Editing Dwight Yoakam (section)

==Musical career==
===1984{{ndash}}1986: ''Guitars, Cadillacs, Etc., Etc.''===
[[File:PeteAnderson(by Scott Dudelson).jpg|200px|thumb|right|[[Pete Anderson]], seen here in 2009, produced and played lead guitar on the majority of Yoakam's albums.|alt=Musician Pete Anderson playing an electric guitar.]]
By 1984, Yoakam had written a large number of songs. Anderson then encouraged him to record some of them on an [[extended play]]. He also served as producer and lead guitarist on the project, roles he would serve throughout most of Yoakam's career.<ref name="encyclopedia"/> The EP was titled ''[[Guitars, Cadillacs, Etc., Etc.]]'' and was released through the [[Oak Records]] label. It consisted of five of Yoakam's original compositions, plus a cover of [[Johnny Cash]]'s "[[Ring of Fire (song)|Ring of Fire]]".<ref name="roots"/> Songs from the extended play received airplay on independent radio stations throughout Los Angeles.<ref name="allmusic"/> Later in the year Yoakam was chosen to serve as an opening act for [[The Blasters]]. This led to him being discovered by [[Reprise Records]] executive Paige Levy, who helped Yoakam sign with the label in 1986.<ref name="roots"/> Reprise re-issued ''Guitars, Cadillacs, Etc., Etc.'' that year with four more tracks, thus making it his debut album.<ref name="allmusic"/> One of the added tracks was "Bury Me", a duet with [[Maria McKee]].<ref name="etc review"/> The first single off the album was a cover of [[Johnny Horton]]'s 1956 single "[[Honky-Tonk Man|Honky Tonk Man]]". Yoakam's rendition of the song charted at number three on ''[[Billboard (magazine)|Billboard]]'' [[Hot Country Songs]] in mid-1986.<ref name="whitburn"/> The song was even more successful in Canada, reaching the number one position on that nation's country music charts then published by ''[[RPM (magazine)|RPM]]''.<ref>{{cite journal | url=https://worldradiohistory.com/CANADA/RPM/80s/1986/RPM-1986-06-28.pdf | title=RPM country singles | journal=RPM | pages=12 | date=June 28, 1986}}</ref> "Honky Tonk Man" also received a [[music video]], which in 1986 became the first by a country artist to air on [[MTV]].<ref name="gq">{{cite web | url=https://www.gq.com/story/dwight-yoakam-honky-tonk-tales | title=Tall Tales With Dwight Yoakam | publisher=[[GQ]] | date=March 17, 2020 | access-date=September 3, 2022 | author=Alex Pappademas}}</ref> The album itself reached the number one position on ''Billboard'' Top Country Albums.<ref name="Country Albums">{{cite magazine|url={{BillboardURLbyName|artist=dwight yoakam|chart=Country Albums C}}|title=Dwight Yoakam Album & Song Chart History – Country Albums|magazine=[[Billboard (magazine)|Billboard]]|publisher=[[Prometheus Global Media]]|access-date=March 2, 2011}}</ref>

Two more singles followed, both of which Yoakam wrote himself. These were "[[Guitars, Cadillacs]]" and "[[It Won't Hurt]]", both of which made Hot Country Songs.<ref name="whitburn">{{cite book|last=Whitburn|first=Joel|title=Hot Country Songs 1944 to 2017|publisher=Record Research, Inc|year=2017|page=412|isbn=978-0-89820-229-8}}</ref> Thirteen years after its release, ''Guitars, Cadillacs, Etc., Etc.'' was [[music recording sales certification|certified double platinum]] by the [[Recording Industry Association of America]] (RIAA), honoring shipments of two million copies in the United States.<ref name="riaa">{{cite web | url=https://www.riaa.com/gold-platinum/?tab_active=default-award&se=dwight+yoakam#search_section | title=Search results for Dwight Yoakam | publisher=[[Recording Industry Association of America]] | access-date=September 2, 2022}}</ref> At the [[29th Annual Grammy Awards]] in 1987, the album was nominated for [[Grammy Award for Best Male Country Vocal Performance]] and "Guitars, Cadillacs" was nominated for [[Grammy Award for Best Country Song|Best Country Song]].<ref name="grammy">{{cite web | url=https://www.grammy.com/artists/dwight-yoakam/16275 | title=Search results for Dwight Yoakam | publisher=Grammy.com | access-date=September 2, 2022}}</ref> The [[Country Music Association]] (CMA) also nominated Yoakam for the Horizon Award (now called Best New Artist) and "Honky Tonk Man" for Music Video of the Year.<ref name="cma">{{cite web | url=https://cmaawards.com/past-winners-and-nominees/?appSession=58F85V8WP97CO980N9W8S4B56XS8G2470X840879749J253D76S72QQKVLHHCI7U3FRISL7313GK7UT19HIK5W299NGJZ3YI6E9P4LN3IRAD87M6YJ5V9W685K3CO5AF | title=Search results for Dwight Yoakam | publisher=[[Country Music Association]] | access-date=September 3, 2022}}</ref> Yoakam also won Top New Male Vocalist at the 1986 [[Academy of Country Music]] (ACM) awards.<ref name="acm">{{cite web | url=https://www.acmcountry.com/winners?awardTitle=dwight+yoakam&awardCategory=&awardYear=&actionButton=Submit | title=Search results for Dwight Yoakam | publisher=[[Academy of Country Music]] | access-date=September 4, 2022}}</ref>

The album was reviewed favorably. Thom Jurek of [[AllMusic]] wrote of the album that it contained influences of [[Bob Dylan]] and [[Bakersfield sound]]. His review also noted the number of personal songs written by Yoakam himself, as well as the cover versions of "Ring of Fire" and [[Ray Price (musician)|Ray Price]]'s "[[Heartaches by the Number]]".<ref name="etc review">{{cite web | url=https://www.allmusic.com/album/guitars-cadillacs-etc-etc-mw0000651008 | title=''Guitars, Cadillacs, Etc. Etc.'' review | publisher=AllMusic | access-date=September 2, 2022 | author=Thom Jurek}}</ref> Ron Fell of ''[[Gavin Report]]''  compared Yoakam's musical image favorably to [[Buddy Holly]] and [[Bruce Springsteen]] while also stating that Yoakam had "an authenticity to his persona".<ref>{{cite journal | url=https://worldradiohistory.com/Archive-All-Music/Gavin-Report/80/86/Gavin-1986-03-14.pdf | title=Ron Fell's personal picks - albums | author=Ron Fell | journal=[[Gavin Report]] | pages=19 | date=March 14, 1986}}</ref> Writing for the ''[[Rapid City Journal]]'', Leonard Running noted the use of [[fiddle]], [[steel guitar]], and [[Dobro]] in the production.<ref name="running">{{cite news | url=https://www.newspapers.com/image/351946671 | title=Dwight Yoakam - ''Guitars, Cadillacs, Etc. Etc.'' | work=[[Rapid City Journal]] | date=April 18, 1986 | access-date=September 2, 2022 | author=Leonard Running | pages=V5}}</ref>

===1987{{Ndash}}1989: ''Hillbilly Deluxe'', ''Buenas Noches from a Lonely Room'', and ''Just Lookin' for a Hit''===
Yoakam's second Reprise album ''[[Hillbilly Deluxe (Dwight Yoakam album)|Hillbilly Deluxe]]'' was released in 1987.<ref name="allmusic"/> The album was also led off by a cover song; specifically, [[Elvis Presley]]'s "[[Little Sister (Elvis Presley song)|Little Sister]]". After this were Yoakam's original compositions "[[Little Ways]]" and "[[Please, Please Baby]]", followed by a cover of [[Lefty Frizzell]]'s "[[Always Late with Your Kisses]]". All four of these cuts made top ten on the country music charts between 1987 and early 1988.<ref name="whitburn"/> "Little Ways" was a number one single on the Canadian ''RPM'' country charts.<ref>{{cite journal | url=https://worldradiohistory.com/CANADA/RPM/80s/1987/RPM-1987-10-24.pdf | title=RPM Country Singles | journal=RPM | pages=20 | date=October 24, 1987}}</ref> Also covered on the album was [[Stonewall Jackson (musician)|Stonewall Jackson]]'s "Smoke Along the Track".<ref name="allmusic deluxe"/> One of the other tracks on the album was "Readin', Rightin', Rt. 23", an autobiographical song which Yoakam wrote about the towns along [[U.S. Route 23 in Kentucky]] near his grandparents' houses.<ref name="roots"/> ''Hillbilly Deluxe'' was certified platinum for shipments of one million copies,<ref name="riaa"/> and earned Yoakam another Grammy Award nomination in the category Best Male Country Vocal Performance.<ref name="grammy"/> It also reached number one on Top Country Albums.<ref name="Country Albums"/> Jurek praised the cover songs in his review for AllMusic, where he compared Yoakam's vocal phrasing favorably to [[Merle Haggard]]. He also noted the use of [[lap steel guitar]] and fiddle in Anderson's production, as well as Yoakam's lyrics on "Readin', Rightin', Rt. 23".<ref name="allmusic deluxe">{{cite web | url=https://www.allmusic.com/album/hillbilly-deluxe-mw0000192537 | title=''Hillbilly Deluxe'' review | publisher=AllMusic | access-date=September 2, 2022}}</ref> An uncredited review in ''[[Music & Media]]'' magazine stated, "The album features sophisticated, yet fresh country music with rollicking C&W guitar lines, supplemented with Yoakam's straight, yearning vocals."<ref>{{cite journal | url=https://worldradiohistory.com/UK/Music-and-Media/80s/1987/M&M-1987-05-16.pdf | title=Albums of the week | journal=[[Music & Media]] | pages=22 | date=May 16, 1987}}</ref>

[[File:Buck Owens.jpg|200px|thumb|left|Yoakam had a number one single in 1988 with "[[Streets of Bakersfield]]", a duet with [[Buck Owens]] (pictured here in 1977).|alt=A black-and-white headshot of singer Buck Owens.]]
His third Reprise album was 1988's ''[[Buenas Noches from a Lonely Room]]''. The album was his third and final to top the ''Billboard'' country albums chart.<ref name="Country Albums"/> Its first two singles were also his only number one entries on Hot Country Songs, both peaking there in 1988. These were a cover of [[Buck Owens]]' "[[Streets of Bakersfield]]" which featured Owens on duet vocals, and "[[I Sang Dixie]]".<ref name="whitburn"/> Before "Streets of Bakersfield" was recorded for the album, Yoakam had contacted Owens (who was retired from performing at the time) and convinced him to sing the song on a television special for [[CBS]]. The commercial success of the studio version also led to Owens ending his retirement and re-signing with [[Capitol Records]] later in the decade.<ref>{{cite web | url=https://www.allmusic.com/artist/buck-owens-mn0000941579/biography | title=Buck Owens biography | publisher=AllMusic | author=Stephen Thomas Erlewine | access-date=September 2, 2022}}</ref> The third single from ''Buenas Noches from a Lonely Room'' was "[[I Got You (Dwight Yoakam song)|I Got You]]"; while this song reached number five on the country charts, the album's title track failed to enter top 40.<ref name="whitburn"/> This album once again featured Maria McKee on backing vocals, along with accompaniment by [[Tejano music|Tejano]] accordionist [[Flaco Jiménez]]. Also covered on the album were [[Hank Locklin]]'s "[[Send Me the Pillow You Dream On]]" and Johnny Cash's "[[Home of the Blues]]". Jurek thought that the album "shows the first signs of beginning to stretch out and be comfortable with his unique approach to hard honky tonk music, Bakersfield-style".<ref>{{cite web | url=https://www.allmusic.com/album/buenos-noches-from-a-lonely-room-mw0000200324 | title=''Buenas Noches from a Lonely Room'' review | publisher=AllMusic | access-date=September 2, 2022}}</ref> ''Buenas Noches from a Lonely Room'' and "Streets of Bakersfield" were respectively nominated for Best Male Country Vocal Performance and [[Grammy Award for Best Country Collaboration with Vocals|Best Country Collaboration with Vocals]] at the [[31st Annual Grammy Awards]].<ref name="grammy"/> The latter also received a CMA nomination for Vocal Event of the Year.<ref name="cma"/>

Yoakam ended the 1980s with his first [[greatest hits]] album, ''[[Just Lookin' for a Hit]]''. The album consisted of eight previously released singles and two newly recorded cover songs. These were of The Blasters' "Long White Cadillac" and [[The Flying Burrito Brothers]]' "Sin City", the latter of which Yoakam recorded as a duet with [[k.d. lang]].<ref name="encyclopedia">{{cite encyclopedia | title=Dwight Yoakam | encyclopedia=The Encyclopedia of Country Music | publisher=Oxford University Press |editor=Michael McCall |editor2=John Rumble |editor3=Paul Kingsbury | year=2012 | pages=605}}</ref><ref>{{cite web | url=https://www.allmusic.com/album/just-lookin-for-a-hit-mw0000205933 | title=''Just Lookin' for a Hit'' | publisher=AllMusic | access-date=September 2, 2022 | author=Thom Jurek}}</ref> "Long White Cadillac" was issued as a single, reaching number 35 on the country music charts.<ref name="whitburn"/><ref name="allmusic"/> The "Sin City" cover received a Grammy nomination for Best Country Vocal Collaboration.<ref name="grammy"/>

===1990{{ndash}}1992: ''If There Was a Way'' and soundtrack contributions===
[[File:KOSTAS - songwriter (cropped).jpg|150px|thumb|right|Kostas wrote several of Yoakam's singles in the 1990s.|alt=Songwriter Kostas in an outdoor setting.]]
In 1990, Yoakam entered the ''Billboard'' country charts for the thirteenth time with "[[Turn It On, Turn It Up, Turn Me Loose]]", which peaked at number eleven.<ref name="whitburn"/> This song led off his fourth studio album ''[[If There Was a Way]]''. The album would account for five more singles between 1990 and 1992: "[[You're the One (Dwight Yoakam song)|You're the One]]", "[[Nothing's Changed Here]]", "[[It Only Hurts When I Cry]]", "[[The Heart That You Own]]", and the [[Patty Loveless]] duet "Send a Message to My Heart". Of these, all except "Send a Message to My Heart" were top-20 country hits.<ref name="whitburn"/> "Turn It On, Turn It Up, Turn Me Loose" was also nominated for a Grammy Award for Best Male Country Vocal Performance, Yoakam's fourth nomination in that category.<ref name="grammy"/>

Unlike his previous albums, Yoakam co-wrote several tracks on ''If There Was a Way'' with other writers. He wrote with [[Roger Miller]] on "It Only Hurts When I Cry", a song to which Miller also contributed backing vocals.<ref name="way liner"/> Yoakam had met Miller at the Grammy Awards and presented him with the title, and Miller agreed to co-write the song after Yoakam stated he was a fan of Miller's music.<ref name="right time">{{cite journal | url=https://worldradiohistory.com/Archive-All-Music/Gavin-Report/90/93/Gavin-Report-1993-03-05.pdf | title=Dwight Yoakam: The Right Time | author=Cyndi Hoelzle | journal=[[Gavin Report]] | pages=40–41 | date=March 5, 1993}}</ref> "Turn It On, Turn It Up, Turn Me Loose" was one of the first successful cuts for Greek-American songwriter [[Kostas (songwriter)|Kostas]].<ref name="new">{{cite journal |last=Simons |first=David |date=May 1994 |title=Made in Montana: Kostas Is A Hitmaking Machine From Way Up North |journal=New Country |volume=1 |issue=3 |pages=20–21 |issn=1074-536X }}</ref> Record producer [[Tony Brown (record producer)|Tony Brown]] had sent Kostas' [[demo (music)|demo]] of the song to Pete Anderson because he thought the song sounded like Yoakam had written it. Because of this, Anderson suggested that Yoakam begin writing songs with Kostas.<ref name="right time"/> The two co-wrote both "Nothing's Changed Here" and "Send a Message to My Heart" on ''If There Was a Way'', leading to further collaborations on subsequent albums.<ref name="whitburn"/> Yoakam had written "You're the One" in 1978 about a woman with whom he had ended a relationship.{{sfn|McLeese|2012|p=36}} In addition to Roger Miller, backing vocals on the album included [[Amy Ray]] (of the [[Indigo Girls]]) and bluegrass musician [[Tim O'Brien (musician)|Tim O'Brien]].<ref name="way liner">{{Cite AV media notes |title=If There Was a Way |others=Dwight Yoakam |date=1990 |type=CD booklet |publisher=Reprise Records |id=7599-26344-2}}</ref> [[Alanna Nash]] of ''[[Entertainment Weekly]]'' rated the album "A", stating that it continued on the "[[hillbilly]]" themes of his previous albums while also containing more [[rock and roll]] influence than its predecessors.<ref name="nash way">{{cite magazine | url=https://ew.com/article/1990/11/02/if-there-was-way/ | title=''If There Was a Way'' review | publisher=February 11, 1990 | magazine=Entertainment Weekly | access-date=September 2, 2022 | author=Alanna Nash}}</ref> Jurek praised the album for rock influences as well, particularly the cover of "[[Let's Work Together]]".<ref name="allmusic way"/>

Yoakam contributed to two movie soundtracks in 1992. First, he cut two songs for ''[[Falling from Grace (film)|Falling from Grace]]'', the 1992 directorial debut of rock singer [[John Mellencamp]]. Yoakam performed Mellencamp's composition "Common Day Man";<ref>{{cite web | url=https://www.allmusic.com/album/falling-from-grace-mw0000277710 | title=''Falling from Grace'' review | publisher=AllMusic | access-date=September 2, 2022}}</ref> the two also joined [[Joe Ely]], [[John Prine]], and [[James McMurtry]] on the track "Sweet Suzanne". Credited to Buzzin' Cousins, this song charted on Hot Country Songs for five weeks in early 1992.<ref>Whitburn, p. 65</ref> It also accounted for Yoakam's second CMA nomination in the category of Vocal Event of the Year.<ref name="cma"/> Later in the year, Yoakam covered Elvis Presley's "[[Suspicious Minds]]" for the soundtrack of ''[[Honeymoon in Vegas]]''. This rendition charted on Hot Country Songs by year's end.<ref name="whitburn"/> In addition to these, he re-recorded "Miner's Prayer", a track from ''Guitars, Cadillacs, Etc., Etc.'', as a duet with bluegrass singer [[Ralph Stanley]] on the latter's 1992 album '' Saturday Night & Sunday Morning''.<ref>{{cite web | url=https://www.billboard.com/music/country/dwight-yoakam-guide-bluegrass-7518949/ | title=Dwight Yoakam's Guide to Bluegrass, From Ralph Stanley to Ricky Skaggs | publisher=Billboard | date=September 28, 2016 | access-date=September 3, 2022 | author=Elias Leight}}</ref> This track was nominated for a Grammy award for Best Country Vocal Collaboration.<ref name="grammy"/> Finally, Yoakam released an album titled ''La Croix d'Amour'' for the European market in 1992. This consisted mainly of selections from other albums, as well as previously unreleased cover songs.<ref name="virgin"/>

===1993{{ndash}}1996: ''This Time'', ''Dwight Live'', and ''Gone''===
For his next studio album, 1993's ''[[This Time (Dwight Yoakam album)|This Time]]'', Yoakam wrote either by himself or in collaboration with Kostas. The only exception was the album's lead single "[[Ain't That Lonely Yet]]", which Kostas co-wrote with [[James House (singer)|James House]].<ref name="Thom Jurek">{{cite web | url=https://www.allmusic.com/album/this-time-mw0000095308 | title=''This Time'' review | publisher=AllMusic | access-date=September 3, 2022 | author=Thom Jurek}}</ref> This song peaked at number two on the ''Billboard'' country charts,<ref name="whitburn"/> while also topping the American ''[[Radio & Records]]'' country music charts and Canadian ''RPM'' country charts.<ref>{{cite journal | url=https://worldradiohistory.com/Archive-All-Music/Archive-RandR/1990s/1993/RR-1993-05-21.pdf | title=R&R Country National Airplay | journal=[[Radio & Records]] | pages=58 | date=May 21, 1993}}</ref><ref>{{cite journal | url=https://worldradiohistory.com/CANADA/RPM/90s/1993/RPM-1993-06-12.pdf | title=RPM 100 Country Tracks | journal=RPM | pages=12 | date=June 12, 1993}}</ref> It won Yoakam the Grammy Award for Best Male Country Vocal Performance in 1993, his first win from that association.<ref name="grammy"/> ''This Time'' charted four more singles between 1993 and 1994. First were "[[A Thousand Miles from Nowhere]]" and "[[Fast as You]]", which both achieved peaks of number two as well. The latter also became Yoakam's first entry on the [[Billboard Hot 100|''Billboard'' Hot 100]], peaking at 70.<ref name="whitburn"/> After these were "[[Try Not to Look So Pretty]]" and "[[Pocket of a Clown]]", which were less successful on the charts.<ref name="whitburn"/> Of the album, Anderson told ''Gavin Report'' that "It's really the first record we've made where we just took all the boundaries down", while Yoakam himself said that "I felt that my musical statements on the preceding albums were valid, but that they were complete statements and there was no need to further articulate them. It was time to allow my music latitude."<ref name="right time"/> He cited the track "Home for Sale" as an example, describing it as a "stone country" lyric backed by a [[Hammond organ]], an instrument not commonly used in country.<ref name="right time"/> Jurek noted influences of [[doo-wop]] in "Pocket of a Clown" and of [[Roy Orbison]] in "Ain't That Lonely Yet".<ref name="Thom Jurek"/> In July 1994, Yoakam began the This Time Tour, a 75-city tour which featured [[Alison Krauss and Union Station]] as an opening act.<ref name="deseret">{{cite web | url=https://www.deseret.com/1994/7/20/19120758/yoakam-s-no-yokel-with-new-hip-image | title=Yoakam's no yokel with new 'hip' image | publisher=[[Deseret News]] | date=July 20, 1994 | access-date=September 3, 2022 | author=Jerry Johnston}}</ref><ref name="right time"/> The Country Music Association nominated "Ain't That Lonely Yet" for Single of the Year in 1993, and Yoakam himself in the category Male Vocalist of the Year in 1994.<ref name="cma"/> The album achieved his highest RIAA certification, for triple-platinum in 1996.<ref name="riaa"/>

[[File:Dwight Yoakam in 2008.jpg|200px|thumb|left|Yoakam performing in 2008.|alt=Country music singer Dwight Yoakam, looking to his side while strumming a guitar.]]

Yoakam released two albums in 1995. The first was ''[[Dwight Live]]'', a live album recorded in July 1994 in [[San Francisco]].<ref name="allmusic"/> Stephen Thomas Erlewine wrote of this album that "nothing on the album improves on the original recorded versions",<ref>{{cite web | url=https://www.allmusic.com/album/dwight-live-mw0000176531 | title=''Dwight Live'' review | publisher=AllMusic | access-date=September 3, 2022 | author=Stephen Thomas Erlewine}}</ref> while Tony Scherman of ''Entertainment Weekly'' thought the album was "beautifully paced" and showed Yoakam's strengths as a vocalist.<ref>{{cite web | url=https://ew.com/article/1995/05/26/dwight-live/ | title=''Dwight Live'' | publisher=Entertainment Weekly | date=May 26, 1995 | access-date=September 3, 2022 | author=Tony Scherman}}</ref> The album was certified gold in 1996.<ref name="riaa"/> His other release for 1995 was the studio album ''[[Gone (Dwight Yoakam album)|Gone]]''. Yoakam wrote the entire album, collaborating with Kostas on two songs. Among the backing vocalists were [[Carl Jackson]], [[Jim Lauderdale]], [[Joy Lynn White]], and [[The Rembrandts]].<ref name="gone liner">{{Cite AV media notes |title=Gone |others=Dwight Yoakam |date=1995 |type=CD booklet |publisher=Reprise Records |id= 9362-46051-2}}</ref> "[[Nothing (Dwight Yoakam song)|Nothing]]", one of the collaborations with Kostas, was selected as the lead single and charted at number 20 on Hot Country Songs in 1995. The song's [[B-side]] "Gone (That'll Be Me)" and "Sorry You Asked?" were released as singles as well, though neither reached top 40.<ref name="whitburn"/> Jurek thought that individual tracks displayed influences of [[rhythm and blues]], [[mariachi]], [[Tejano music]], and [[psychedelic rock]].<ref name="gone allmusic">{{cite web | url=https://www.allmusic.com/album/gone-mw0000645809 | title=''Gone'' review | publisher=AllMusic | access-date=September 3, 2022 | author=Thom Jurek}}</ref> Jeffrey B. Remz of [[Country Standard Time]] wrote that ''Gone'' was "a critically received album, which did not do boffo numbers because Yoakam received very little airplay for what was probably his most musically diverse album. And in some parts of the country, his tour did not draw crowds either."<ref name="covers"/>

===1997{{ndash}}1998: ''Under the Covers'', ''Come On Christmas'', ''A Long Way Home''===
Yoakam's next release for Reprise was 1997's ''[[Under the Covers (Dwight Yoakam album)|Under the Covers]]'', an album composed entirely of cover songs.<ref name="allmusic"/> Yoakam and Anderson had begun recording songs for this project prior to ''Gone'', while other selections previously appeared on ''La Croix d'Amour''.<ref name="covers">{{cite web | url=https://www.countrystandardtime.com/d/print_article.asp?xid=900 | title=Dwight Yoakam peeks out from 'under the covers' | publisher=Country Standard Time | date=July 1997 | access-date=September 3, 2022 | author=Jeffrey B. Remz}}</ref> The project accounted for only one single in a rendition of [[The Everly Brothers]]' "Claudette".<ref name="whitburn"/> Bluegrass musician [[Ralph Stanley]] played banjo on a cover of [[The Clash]]'s "[[Train in Vain]]", while [[Sheryl Crow]] sang duet vocals on a cover of [[Sonny & Cher]]'s "[[Baby Don't Go]]". Jurek wrote of this album, "While this set is not perfect, it's still damn fine and warrants repeated listens to come to grips with Yoakam's visionary ambition."<ref>{{cite web | url=https://www.allmusic.com/album/under-the-covers-mw0000024521 | title=''Under the Covers'' review | publisher=AllMusic | access-date=September 3, 2022 | author=Thom Jurek}}</ref> Remz praised the covers of [[Glen Campbell]]'s "[[Wichita Lineman]]" and "Train in Vain" in particular, but criticized the cover of [[The Beatles]]' "[[Things We Said Today]]".<ref>{{cite web | url=https://www.countrystandardtime.com/d/cdreview.asp?xid=977 | title=''Under the Covers'' review | publisher=Country Standard Time | access-date=September 3, 2022 | author=Jeffrey B. Remz}}</ref> After this was an album of [[Christmas music]] titled ''[[Come On Christmas]]'', released later in the year. Yoakam wrote the title track and "Santa Can't Stay", while the rest of the album largely consisted of traditional Christmas songs such as "[[Away in a Manger]]" and "[[Silver Bells]]". Thom Owens of AllMusic wrote that the album contained "high-spirited, entertaining country-rockers that may not add anything new to Yoakam's catalog, but they make the record an enjoyable holiday album."<ref>{{cite web | url=https://www.allmusic.com/album/come-on-christmas-mw0000025120 | title=''Come On Christmas'' review | publisher=AllMusic | access-date=September 3, 2022 | author=Thom Owens}}</ref>

Between 1995 and 1997, Yoakam received three consecutive Grammy nominations in the category of Best Male Country Vocal Performance. The songs nominated in this category were "Pocket of a Clown", "A Thousand Miles from Nowhere", and "Nothing". He also received three consecutive nominations for [[Grammy Award for Best Country Album|Best Country Album]] between 1996 and 1998, with the nominations going to ''Dwight Live'', ''Gone'', and ''Under the Covers''.<ref name="grammy"/> After these was his next studio album of original content, 1998's ''[[A Long Way Home (album)|A Long Way Home]]''.<ref name="allmusic"/> Yoakam wrote the entire project by himself, making it his first not to have any co-writers or cover songs.{{sfn|McLeese|2012|p=163}} The album charted two singles in "[[Things Change (Dwight Yoakam song)|Things Change]]" and "These Arms".<ref name="whitburn"/> This album also featured Ralph Stanley, this time as a duet partner on "Traveler's Lantern".<ref name="cst"/> Brian Steinberg of Country Standard Time thought that the album was "back to basics" and comparable to Yoakam's releases in the 1980s, stating that "This isn't Yoakam's most innovative work, but it contains enough moments to make it worth attention."<ref name="cst">{{cite web | url=https://www.countrystandardtime.com/d/cdreview.asp?xid=2149 | title=''A Long Way Home'' review | publisher=Country Standard Time | access-date=September 3, 2022 | author=Brian Steinberg}}</ref> Also in 1998, Yoakam funded a charity album for release on Little Dog Records, a label which his then-producer and guitarist Pete Anderson owned. This album was titled ''Will Sing for Food'' and featured other artists recording renditions of Yoakam's songs. Among the artists contributing were [[Sara Evans]], [[Mandy Barnett]], [[Kim Richey]], [[Gillian Welch]], and [[David Ball (country singer)|David Ball]].<ref>{{cite magazine | url=https://books.google.com/books?id=rg4EAAAAMBAJ | title=Nashville Scene | author=Chet Flippo | magazine=Billboard | pages=57 | date=April 11, 1998}}</ref> Nash contrasted these two albums in a double review, calling ''A Long Way Home'' "a fresh, dynamic set, updating his trademark Bakersfield-does-L.A. sound without sacrificing his honky-tonk roots" while stating that ''Will Sing for Food'' had "stunningly original interpretations".<ref>{{cite web | url=https://ew.com/article/1998/06/12/long-way-homewill-sing-food/ | title=''A Long Way Home'' / ''Will Sing for Food'' review | publisher=Entertainment Weekly | date=June 12, 1998 | access-date=September 3, 2022 | author=Alanna Nash}}</ref> Steinberg gave the latter a mixed review, praising the contributions of [[Bonnie Bramlett]] and [[Scott Joss]] while considering other cuts on the album too similar in sound to Yoakam's originals.<ref>{{cite web | url=https://www.countrystandardtime.com/d/cdreview.asp?xid=2150 | title=''Will Sing for Food'' review | publisher=Country Standard Time | access-date=September 3, 2022 | author=Brian Steinberg}}</ref>

===1998{{ndash}}1999: ''Last Chance for a Thousand Years: Dwight Yoakam's Greatest Hits from the 90's''===
[[File:Queen – montagem – new.png|200px|thumb|right|Yoakam had a hit in 1999 with a cover of Queen's "Crazy Little Thing Called Love".|alt=A composite image showing the four members of the band Queen.]]
In 1998, [[Columbia Records]] released ''[[A Tribute to Tradition]]'', a multi-artist tribute album to 1960s and 1970s country music. Yoakam was one of several artists featured on the album's closing track "Same Old Train", an original composition by [[Marty Stuart]].<ref>{{cite web | url=https://www.allmusic.com/album/a-tribute-to-tradition-mw0000600042 | title=''A Tribute to Tradition'' | publisher=AllMusic | access-date=September 3, 2022 | author=Jana Pendragon}}</ref> The track featured twelve other country musicians, including [[Earl Scruggs]], [[Merle Haggard]], [[Clint Black]], and [[Randy Travis]]. It charted for five weeks on Hot Country Songs in late 1998.<ref>Whitburn, p. 316</ref> The song won Grammy Award for Best Country Collaboration with Vocals at the [[41st Annual Grammy Awards]], thus giving Yoakam his second win from the organization.<ref name="grammy"/> It was also nominated for CMA Vocal Event of the Year.<ref name="cma"/>

Yoakam ended the decade with his second greatest-hits package, ''[[Last Chance for a Thousand Years: Dwight Yoakam's Greatest Hits from the 90's]]''. In addition to tracks from his 1990s Reprise albums, the compilation included three new songs. These were covers of [[Queen (band)|Queen]]'s "[[Crazy Little Thing Called Love]]" and [[Waylon Jennings]]' "I'll Go Back to Her" and the new song "Thinking About Leaving", which Yoakam wrote with [[Rodney Crowell]].<ref>{{cite web | url=https://www.allmusic.com/album/mw0000243327 | title=''Last Chance for a Thousand Years: Dwight Yoakam's Greatest Hits from the 90's'' | publisher=AllMusic | access-date=September 3, 2022 | author=Stephen Thomas Erlewine}}</ref> The cover of "Crazy Little Thing Called Love" served as the album's lead single, peaking at 12 on the country charts and 64 on the Hot 100.<ref name="whitburn"/> It was also his final number one on the Canadian country music charts published by ''RPM'' before that publication closed in 2000.<ref>{{cite journal | url=https://worldradiohistory.com/CANADA/RPM/90s/1999/RPM-1999-08-16.pdf | title=RPM Country 100 | journal=RPM | pages=14 | date=August 16, 1999}}</ref> "Thinking About Leaving" was also issued as a single, but did not enter the country music top 40.<ref name="whitburn"/> In 2000, "Crazy Little Thing Called Love" was nominated for a Grammy Award for Best Male Country Vocal Performance.<ref name="grammy"/>

===2000{{ndash}}01: ''dwightyoakamacoustic.net'' and ''Tomorrow's Sounds Today''===
Yoakam's tenure with Reprise Records ended with a pair of albums both released in 2000. The first was ''[[dwightyoakamacoustic.net]]'', composed entirely of acoustic recordings with just Yoakam's vocal and acoustic guitar. The only exception was a re-recording of "Guitars, Cadillacs", which Yoakam performed ''[[a cappella]]''.<ref name="acoustic"/> Yoakam said that he was inspired to do such an album due to the success of similar acoustic renditions in his concerts. He had originally planned to release the album through his website until representatives of Reprise Records thought the album had sales potential. The album itself had minimalistic packaging as well, consisting solely of a sticker with the album's name on the front of an otherwise-clear CD case.<ref>{{cite news | url=https://www.newspapers.com/image/429082785 | title=Dwight Yoakam returns to basics | work=[[Times Leader|The Times Leader]] | date=July 28, 2000 | access-date=September 3, 2022 | author=Mario Tarradell | pages=13}}</ref> Steve Huey of AllMusic thought that the album's minimalism allowed a greater focus on Yoakam's vocal interpretation than previous albums.<ref name="acoustic">{{cite web | url=https://www.allmusic.com/album/dwightyoakamacousticnet-mw0000064106 | title=''dwightyoakamacoustic.net'' | publisher=AllMusic | access-date=September 3, 2022 | author=Steve Huey}}</ref>

His other release in 2000 was ''[[Tomorrow's Sounds Today]]''.<ref name="allmusic"/> The album accounted for two charted singles in "[[What Do You Know About Love]]" and a cover of [[Cheap Trick]]'s "[[I Want You to Want Me]]".<ref name="whitburn"/> Yoakam co-wrote with Buck Owens on three tracks: "The Sad Side of Town", "Alright, I'm Wrong", and "I Was There", the latter two of which were also recorded as duets with him. Although the two had previously sung together on "Streets of Bakersfield", Owens rejected further collaborations throughout the 1990s as he considered Yoakam "too young", but ultimately agreed to collaborate again when the two met at a concert in 1999.<ref name="route 23">{{cite web | url=https://www.cmt.com/news/rnp7tc/dwight-yoakam-route-23-came-west-too | archive-url=https://web.archive.org/web/20220904022745/https://www.cmt.com/news/rnp7tc/dwight-yoakam-route-23-came-west-too | url-status=dead | archive-date=September 4, 2022 | title=Dwight Yoakam: Route 23 came west, too | publisher=CMT | date=November 14, 2001 | access-date=September 3, 2022 | author=Robert Price}}</ref> Writing for AllMusic, Hal Horowitz thought the Owens collaborations showed Yoakam's continued influence of the [[Bakersfield sound]] of which Owens was a part. He also praised the guitar work of Pete Anderson and compared Yoakam's lyrical style to that of [[Hank Williams]].<ref name=TST>{{cite web | url=https://www.allmusic.com/album/tomorrows-sounds-today-mw0000102926 | title=''Tomorrow's Sounds Today'' | publisher=AllMusic | access-date=September 3, 2022 | author=Hal Horowitz}}</ref> Scherman was less favorable, considering the material "forgettable" despite describing Anderson's guitar work with favor.<ref>{{cite web | url=https://ew.com/article/2000/11/03/tomorrows-sounds-today/ | title=''Tomorrow's Sounds Today'' | publisher=Entertainment Weekly | date=November 3, 2000 | access-date=September 3, 2022 | author=Tony Scherman}}</ref> Yoakam received his final CMA nomination in 2001, when that institution nominated "Alright, I'm Wrong" for Vocal Event of the Year.<ref name="cma"/> At the end of his contract with Reprise, parent company [[Warner Records]] issued a [[box set]] album titled ''[[Reprise Please Baby: The Warner Bros. Years]]''. The package consisted of 89 tracks from Yoakam's Reprise catalog, including previously unreleased songs and early demos. Also included was a duet with [[Kelly Willis]] on a cover of [[George Jones]] and [[Tammy Wynette]]'s "[[Golden Ring (song)|Golden Ring]]".<ref>{{cite web | url=https://www.cmt.com/news/9ojtwc/yoakam-gets-boxed-set-treatment | archive-url=https://web.archive.org/web/20220904022743/https://www.cmt.com/news/9ojtwc/yoakam-gets-boxed-set-treatment | url-status=dead | archive-date=September 4, 2022 | title=Yoakam gets boxed set treatment | publisher=[[CMT (American TV channel)|CMT]] | date=September 20, 2002 | access-date=September 3, 2022}}</ref>

===2002{{ndash}}04: ''Population Me'' and compilations===
Yoakam spent much of 2001 and 2002 touring with [[Brooks & Dunn]]. He also founded a new record label called Electrodisc after his contract with Reprise expired.<ref>{{cite web | url=https://www.cmt.com/news/g7y1yg/yoakams-next-cd-will-be-an-electrodisc | archive-url=https://web.archive.org/web/20220904033829/https://www.cmt.com/news/g7y1yg/yoakams-next-cd-will-be-an-electrodisc | url-status=dead | archive-date=September 4, 2022 | title=Yoakam's next CD will be an electrodisc | publisher=CMT | date=July 25, 2002 | access-date=September 3, 2022 | author=Jay Orr}}</ref> The label partnered with Audium Records (now [[MNRK Music Group]]) for distribution.<ref>{{cite web | url=https://www.cmt.com/news/v5arko/yoakam-brings-electrodisc-to-audium | archive-url=https://web.archive.org/web/20220904021240/https://www.cmt.com/news/v5arko/yoakam-brings-electrodisc-to-audium | url-status=dead | archive-date=September 4, 2022 | title=Yoakam brings electrodisc to Audium | publisher=[[CMT (American TV channel)|CMT]] | date=November 20, 2002 | access-date=September 3, 2022}}</ref> His first Audium release was 2003's ''[[Population Me]]''.<ref name="allmusic"/> This album charted two singles, both of which were covers: [[Gregg Henry]]'s "The Back of Your Hand" and [[Mike Stinson]]'s "The Late Great Golden State".<ref name="whitburn"/> Also covered on this album was [[Burt Bacharach]]'s "[[Trains and Boats and Planes]]". [[Timothy B. Schmit]] provided backing vocals on "The Late Great Golden State", while [[Willie Nelson]] sang duet vocals on "If Teardrops Were Diamonds". Jurek found influences of [[Jackson Browne]], the [[Eagles (band)|Eagles]], and [[Chuck Berry]] in the album's sound.<ref>{{cite web | url=https://www.allmusic.com/album/population-me-mw0000031097 | title=''Population Me'' | publisher=AllMusic | access-date=September 3, 2022 | author=Thom Jurek}}</ref> Messinger wrote of the album that "the complex, innovative sound he and Anderson have developed certainly merits repeated exploration."<ref>{{cite web | url=https://www.countrystandardtime.com/d/cdreview.asp?xid=971 | title=''Population Me'' review | publisher=Country Standard Time | access-date=September 5, 2022 | author=Eli Messinger}}</ref>

Between 2003 and 2004, Yoakam released three more compilations of covers albums to fulfill contractual obligations with his labels.{{sfn|McLeese|2012|p=191}} The first was 2003's ''[[In Others' Words]]'' on Reprise. This consisted entirely of cover songs mostly from movie soundtracks and tribute albums to which Yoakam contributed. The oldest track was a cover of the [[Grateful Dead]]'s "[[Truckin']]", which Yoakam cut in 1991.<ref>{{cite web | url=https://www.cmt.com/news/jmw6sl/yoakams-second-album-of-covers-due | archive-url=https://web.archive.org/web/20220904035338/https://www.cmt.com/news/jmw6sl/yoakams-second-album-of-covers-due | url-status=dead | archive-date=September 4, 2022 | title=Yoakam's second album of covers due | publisher=CMT | date=July 30, 2003 | access-date=September 3, 2022}}</ref> Jurek wrote that the compilation was "far from a stellar set but does fill in the gaps nicely."<ref>{{cite web | url=https://www.allmusic.com/album/in-others-words-mw0000317949 | title=''In Others' Words'' | publisher=AllMusic | access-date=September 3, 2022}}</ref> [[Rhino Records]] released a greatest-hits package titled ''[[The Very Best of Dwight Yoakam]]'' in 2004. This compilation was certified gold after its release.<ref name="riaa"/> Erlewine thought that while the album did not contain many of his earlier songs, it otherwise showed the range of his styles and would have potential appeal to fans who preferred his more rock-influenced cuts such as the covers of "Crazy Little Thing Called Love" and "I Want You to Want Me".<ref>{{cite web | url=https://www.allmusic.com/album/the-very-best-of-dwight-yoakam-mw0000207796 | title=''The Very Best of Dwight Yoakam'' | publisher=AllMusic | access-date=September 5, 2022 | author=Stephen Thomas Erlewine}}</ref> His third and final compilation was ''[[Dwight's Used Records]]'' on Audium also in 2004. Among the collaborators on this project were [[Heather Myles]], [[Deana Carter]], and the [[Nitty Gritty Dirt Band]]. Artists covered included [[John Prine]]'s "[[Paradise (John Prine song)|Paradise]]", [[ZZ Top]]'s "[[I'm Bad, I'm Nationwide]]", and [[Johnny Cash]]'s "[[Understand Your Man]]".<ref>{{cite web | url=https://www.allmusic.com/album/dwights-used-records-mw0000333310 | title=''Dwight's Used Records'' | publisher=AllMusic | access-date=September 3, 2022 | author=Mark Deming}}</ref> Country Standard Time writer Eli Messinger thought that, by drawing from a decade's worth of material, the album showed new variety in Yoakam's style over his traditional studio albums.<ref>{{cite web | url=https://www.countrystandardtime.com/d/cdreview.asp?xid=970 | title=''Dwight's Used Records'' | publisher=Country Standard Time | access-date=September 3, 2022 | author=Eli Messinger}}</ref>

===2005{{ndash}}2007: ''Blame the Vain'' and ''Dwight Sings Buck''===
In 2005, Yoakam signed with [[New West Records]], an [[Americana music]] label based out of California. His first release for the label was 2005's ''[[Blame the Vain]]''. It was also Yoakam's first credit as a producer, as he had ended his relationship with Pete Anderson in 2004. At the time, former [[RCA Records]] artist [[Keith Gattis]] had taken over as Yoakam's guitarist and bandleader.{{sfn|McLeese|2012|p=191-192}} Yoakam said that he had contacted a number of producers until Gattis encouraged him to produce by himself.<ref name="joyful">{{cite magazine | url=https://books.google.com/books?id=zhQEAAAAMBAJ | title=A joyful return for Yoakam | author=Phyllis Stark | magazine=Billboard | pages=39, 40 | date=June 25, 2005}}</ref> New West partnered with [[Columbia Records]] to release two singles to radio.<ref name="joyful"/> These were "Intentional Heartache" and the title track, which both made the lower regions of the country charts in 2005 and accounted for Yoakam's last appearance there.<ref name="whitburn"/> In the book ''Dwight Yoakam: A Thousand Miles from Nowhere'', Don McLeese thought that Anderson's absence gave the album "an unbridled lack of restraint", citing the [[hard rock]] sound and spoken-word coda of "Intentional Heartache" as examples.{{sfn|McLeese|2012|p=192-193}} Ray Waddell of ''Billboard'' also noted a "hard-charging" sound to the album, comparing various tracks to [[Elvis Presley]].<ref>{{cite magazine | url=https://books.google.com/books?id=zBQEAAAAMBAJ | title=Reviews | author=Ray Waddell | magazine=Billboard | pages=42 | date=July 2, 2005}}</ref> Rhino Records re-issued ''Guitars, Cadillacs, Etc, Etc.'' in 2006 to honor the album's 20th anniversary. This re-issue included previously unreleased demos and live tracks, along with liner notes written by Yoakam.<ref>{{cite web | url=http://www.cmt.com/news/vnltt4/dwight-yoakams-debut-album-to-be-reissued-expanded | archive-url=https://web.archive.org/web/20220904035123/https://www.cmt.com/news/vnltt4/dwight-yoakams-debut-album-to-be-reissued-expanded | url-status=dead | archive-date=September 4, 2022 | title=Dwight Yoakam's debut album to be reissued, expanded | publisher=CMT | date=July 25, 2006 | access-date=September 3, 2022}}</ref>

After Buck Owens' death in 2006, Yoakam began performing covers of his songs in concert. This culminated in his 2007 album ''[[Dwight Sings Buck]]'', composed entirely of Owens covers. Yoakam recorded the project with his touring band, which at the time included then-former [[The Mavericks|Mavericks]] member [[Eddie Perez (guitarist)|Eddie Perez]] on lead guitar. Yoakam stated that he and the band listened to Owens' originals to draw inspiration from the recordings. Among the songs chosen were "[[Act Naturally]]", "[[Crying Time]]", and "Close Up the Honky Tonks", the last of which served as the lead single.<ref>{{cite magazine | url=https://books.google.com/books?id=ow4EAAAAMBAJ | title=Nashville Scene | author=Ken Tucker | magazine=Billboard | pages=65 | date=October 13, 2007}}</ref> A review in AllMusic was favorable, stating that "He doesn't set out to imitate Owens' style or delivery, but he does capture the essence of each song, playing them as Buck intended: no frills, no foolin' around".<ref>{{cite web | url=https://www.allmusic.com/album/dwight-sings-buck-mw0000488962 | title=''Dwight Sings Buck'' | publisher=AllMusic | access-date=September 3, 2022 | author=Jeff Tamarkin}}</ref>

===2008{{ndash}}2020: ''3 Pears'', ''Second Hand Heart'', and ''Swimmin' Pools, Movie Stars...''===
[[File:BeckMSG190718-13 (47065153261) (cropped).jpg|200px|thumb|left|Beck produced two tracks on Yoakam's 2012 album ''3 Pears''.|alt=Musician Beck, wearing a black suit and hat, and holding an electric guitar.]]
Yoakam performed at the [[CMA Music Festival]] in [[Nashville, Tennessee]], in 2008, where he was joined by [[Faith Hill]]. This was Yoakam's first appearance at the event in over 20 years.<ref>{{cite news | url=https://www.newspapers.com/image/282417510/ | title=Dwight Yoakam back at CMA fest | work=[[The Jackson Sun]] | date=June 6, 2008 | access-date=September 3, 2022 | pages=2B}}</ref> He otherwise performed very few concerts in 2009 and 2010, citing the [[Great Recession]] and the rise of digital music distribution as a reason behind the slower pace of his career at the time. Despite this, he still stated that he planned to continue releasing albums.<ref>{{cite news | url=https://www.newspapers.com/image/505268525/ | title=Country star has eyes on the digital future | work=[[The Record (North Jersey)|The Record]] | date=January 7, 2010 | access-date=September 3, 2022 | author=David J. Spatz}}</ref> In July 2011, he re-signed with Warner for his next album, 2012's ''[[3 Pears]]''.<ref>{{cite news | url=https://www.cmt.com/news/mzcybw/dwight-yoakam-reunites-with-warner-music-group-for-new-album | archive-url=https://web.archive.org/web/20220904033827/https://www.cmt.com/news/mzcybw/dwight-yoakam-reunites-with-warner-music-group-for-new-album | url-status=dead | archive-date=September 4, 2022 | title=Dwight Yoakam reunites with Warner Music Group for new album | work=CMT | date=July 5, 2011 | access-date=September 3, 2022}}</ref> The album included production from rock musician [[Beck]] on two tracks. Upon release, it became Yoakam's highest entry on the [[Billboard 200|''Billboard'' 200]] albums chart, reaching number 18.<ref name="allmusic"/> Mikael Wood of the ''Los Angeles Times'' thought the album displayed a "softer side" than Yoakam's previous efforts.<ref>{{cite web|url=https://www.latimes.com/entertainment/music/la-xpm-2012-oct-04-la-et-ms-dwight-yoakam-3-pears-20121005-story.html|title=Dwight Yoakam shows a softer side on '3 Pears'|last=Wood|first=Mikael|date=October 4, 2012|work=[[Los Angeles Times]]|access-date=May 7, 2020}}</ref> Stephen Thomas Erlewine wrote of the album, "Yoakam has surprised by digging deeper into every one of his obsessions, creating a record that captures the careening, adventurous spirit of the '60s without ever feeling doggedly retro. It's as fresh as any music he's ever made, and one of his very best albums."<ref>{{cite web | url=https://www.allmusic.com/album/mw0002408332 | title=''3 Pears'' | publisher=AllMusic | access-date=September 3, 2022 | author=Stephen Thomas Erlewine}}</ref>

His next Warner album was 2015's ''[[Second Hand Heart (album)|Second Hand Heart]]''. It reached the number two position on Top Country Albums after its release, his highest peak on that chart since ''Buenas Noches from a Lonely Room'' in 1988.<ref>{{cite magazine|last1=Trust|first1=Gary|title=Reba McEntire, George Strait & Dwight Yoakam Return to Country Charts|url=https://www.billboard.com/articles/columns/chart-beat/6545726/reba-mcentire-george-strait-dwight-yoakam-country-charts|access-date=April 23, 2015|magazine=[[Billboard (magazine)|Billboard]]|date=April 23, 2015}}</ref> It consisted almost entirely of original songs written by Yoakam, except a cover of the standard "[[Man of Constant Sorrow]]" and [[Anthony Crawford (musician)|Anthony Crawford]]'s "V's of Birds". Erlewine found influences of The Beatles, Buck Owens, and [[cowpunk]] in the album's arrangements.<ref>{{cite web | url=https://www.allmusic.com/album/second-hand-heart-mw0002820353 | title=''Second Hand Heart'' | publisher=AllMusic | access-date=September 3, 2022}}</ref> Ann Powers of [[NPR]]'s First Listen shared a similar opinion of the album, also praising the "brightness" of its sound.<ref>{{cite web | url=https://www.npr.org/2015/04/05/396881299/first-listen-dwight-yoakam-second-hand-heart | title=Review: Dwight Yoakam, 'Second Hand Heart' | publisher=NPR | date=April 5, 2015 | access-date=September 3, 2022 | author=Ann Powers}}</ref>

In 2016 Yoakam was contacted by a label executive of [[Sugar Hill Records (bluegrass label)|Sugar Hill Records]], who wanted him to record a [[bluegrass music]] album for them.<ref name="odessa"/> This album, ''[[Swimmin' Pools, Movie Stars...]]'', was released that same year. It mostly comprises re-recordings of previous songs in his career, including "Guitars, Cadillacs" and "Please, Please Baby".<ref name="dauphin"/> Yoakam co-produced with [[Jon Randall]] and [[Gary Paczosa]].<ref>{{cite news |last1=Thanki |first1=Juli |title=Back to bluegrass |work=The Tennessean |date=August 3, 2016 |page=A2}}</ref> The album included musical accompaniment by [[Alison Krauss & Union Station]] members [[Adam Steffey]] and [[Barry Bales]] on [[mandolin]] and [[upright bass]] respectively. Also contributing were guitarist [[Bryan Sutton]], fiddler [[Stuart Duncan]], and banjoist [[Scott Vestal]].<ref name="odessa">{{cite news | url=https://www.newspapers.com/image/507568787 | title=Country legend on stage Oct. 20 | work=[[The Odessa American]] | date=October 12, 2018 | access-date=September 4, 2022 | pages=6A}}</ref> In addition to his own material, Yoakam covered [[Prince (musician)|Prince]]'s "[[Purple Rain (song)|Purple Rain]]".<ref name="dauphin">{{cite web | url=https://www.soundslikenashville.com/reviews/album-review-dwight-yoakams-swimmin-pools-movie-stars/ | title=Album review: Dwight Yoakam's ''Swimmin' Pools, Movie Stars...'' | publisher=Sounds Like Nashville | date=September 22, 2016 | access-date=September 3, 2022 | author=Chuck Dauphin}}</ref> Yoakam chose to cover the song the day Prince died, as he had seen the news of the musician's death on television prior to recording.<ref>{{cite news |last1=Devlin |first1=Mike |title=Yoakam's rebellious streak burns bright; Country star to play Manitoulin Country Fest in August |work=The Sudbury Star |date=January 28, 2017 |page=C3}}</ref> Chuck Dauphin of Sounds Like Nashville thought the album brought out the bluegrass influences already present in such songs as "What I Don't Know".<ref name="dauphin"/> Deming called the album "a stylistic detour for Dwight Yoakam, but its execution sums up many of his greatest strengths as an artist".<ref>{{cite web | url=https://www.allmusic.com/album/swimmin-pools-movie-stars-mw0002974546 | title=''Swimmin' Pools, Movie Stars...'' | publisher=AllMusic | access-date=September 3, 2022 | author=Mark Deming}}</ref> Also in 2016, Yoakam released covers of [[The Monkees]]' "Tomorrow's Gonna Be Another Day" and [[Johnny Rivers]]' "[[Mountain of Love]]" on limited edition vinyl through [[Third Man Records]], a label owned by [[Jack White]].<ref>{{cite web|url=https://theboot.com/dwight-yoakam-special-edition-third-man-records/|title=Dwight Yoakam to Release Special Edition Vinyl Via Third Man Records|work=The Boot|date=June 10, 2016}}</ref>

===2017{{ndash}}present: Bakersfield Beat and ''Brighter Days''===
In 2017, Yoakam covered "Wichita Lineman" at a tribute ceremony to songwriter [[Jimmy Webb]] held at [[Carnegie Hall]].<ref>{{cite web | url=https://www.rollingstone.com/music/music-country/see-dwight-yoakams-powerful-wichita-lineman-at-jimmy-webb-tribute-119542/ | title=See Dwight Yoakam's Powerful 'Wichita Lineman' at Jimmy Webb Tribute | publisher=Rolling Stone | date=May 4, 2017 | access-date=September 4, 2022 | author=Stephen L. Betts}}</ref> In 2018, Yoakam was selected by [[SiriusXM]] satellite radio to curate his own show, Bakersfield Beat, on that company's Prime Country channel. The success of this led to Yoakam receiving his own channel also named Bakersfield Beat, in which he plays his own songs as well as those in the genres of [[Bakersfield sound]], [[cowpunk]], and [[country rock]].<ref>{{cite web | url=https://www.rollingstone.com/music/music-country/dwight-yoakam-to-program-new-siriusxm-channel-the-bakersfield-beat-206159/ | title=Dwight Yoakam to Program New SiriusXM Channel 'The Bakersfield Beat' | publisher=[[Rolling Stone]] | date=February 22, 2018 | access-date=September 4, 2022 | author=Jeff Gage}}</ref> In 2022, he started the LSD Tour with [[Lucinda Williams]] and [[Steve Earle]].<ref>{{cite web | url=https://www.daily-jeff.com/story/news/2022/02/01/dwight-yoakam-brings-his-lsd-tour-wheeling/9271868002/ | title=What's the Buzz: Dwight Yoakam brings his LSD Tour to Wheeling | publisher=The Daily Jeff | date=February 1, 2022 | access-date=September 3, 2022 | author=Heather Sevigny}}</ref> He also performed a concert with [[Old Crow Medicine Show]] in 2022 to honor the 30th anniversary of ''Hillbilly Deluxe''.<ref>{{cite web | url=https://www.theoaklandpress.com/2022/08/24/dueling-dudes-keith-urban-dwight-yoakam/ | title=Dueling Dudes: Keith Urban, Dwight Yoakam to perform Friday | publisher=[[The Oakland Press]] | date=August 24, 2022 | access-date=September 3, 2022 | author=Gary Graff}}</ref>

Yoakam announced in November 2024 the release of his first studio album in nine years, ''[[Brighter Days (Dwight Yoakam album)|Brighter Days]]''. The album is his first for Via Records/[[Thirty Tigers]] and it includes the single "I'll Pay the Price". Also released in advance of the album was a duet with [[Post Malone]] titled "I Don't Know How to Say Goodbye (Bang Bang Boom Boom)". The project, produced by Yoakam, also includes covers of [[Cake (band)|Cake]]'s "Bound Away" and [[the Byrds]]'s "Time Between".<ref>{{cite web | url=https://www.countrystandardtime.com/news/newsitem.asp?xid=14340 | title=Yoakam proclaims "I'll Pay The Price" | publisher=Country Standard Time | date=November 6, 2024 | accessdate=November 6, 2024}}</ref>