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===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"/>
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