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===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>
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