Yoakam also has two number-one singles on Hot Country Songs with "Streets of Bakersfield" (a duet with Buck Owens) and "I Sang Dixie", and twelve additional top-ten hits.

He is known for his distinctive tenor singing voice, unconventional musical image, and the lead guitar work of his longtime producer and bandleader Pete Anderson.

[5] Hillbilly Deluxe was certified platinum for shipments of one million copies,[12] and earned Yoakam another Grammy Award nomination in the category Best Male Country Vocal Performance.

[2] 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.

[21] The third single from Buenas Noches from a Lonely Room was "I Got You"; while this song reached number five on the country charts, the album's title track failed to enter top 40.

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".

[27] In addition to Roger Miller, backing vocals on the album included Amy Ray (of the Indigo Girls) and bluegrass musician Tim O'Brien.

Yoakam performed Mellencamp's composition "Common Day Man";[30] the two also joined Joe Ely, John Prine, and James McMurtry on the track "Sweet Suzanne".

[2] 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.

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.

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".

[47] 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".

[48] 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.

These were covers of 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.

[2] 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.

[74] 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".

[79] 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.

[81] It consisted almost entirely of original songs written by Yoakam, except a cover of the standard "Man of Constant Sorrow" and Anthony Crawford's "V's of Birds".

[86] The album included musical accompaniment by Alison Krauss & Union Station members Adam Steffey and Barry Bales on mandolin and upright bass respectively.

[88] 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.

[102] Zac Johnson of AllMusic criticized the soundtrack for including snippets of film dialogue between tracks, although he praised the individual songs and their inclusion of collaborators such as Bekka Bramlett, Mick Jagger, and Billy Gibbons.

Before the movie's release, he told the Associated Press that he did not consider acting significantly different from recording music because both roles were "fragmented" and required "repetition of performance".

"[108] Cyndi Hoelzle of Gavin Report noted Yoakam's appeal outside traditional country music, stating in 1993 that "[h]is records sold across the board-to middle-aged Stonewall Jackson fans and to young punk rockers who'd seen Dwight do his thing in L.A., opening shows for Los Lobos and the Violent Femmes.

"[25] Richard Cromelin of The Los Angeles Times noted that Yoakam's musical image was that of a "brooding, intensely private figure driven by restless ambition and an edgy intellectuality more commonly found in rock stars.

[110] Of these criticisms, he later stated that "I learned a couple albums in... that my opinions and observations on the industry were not pertinent to what I needed to do as an artist, so I just really began to focus solely on what I was doing at the time.

"[6] Alanna Nash wrote in a review of If There Was a Way that "When Dwight Yoakam first came on the scene, with his hip retro-attitude, concha-studded jeans, and music that often grazed the edge of rock & roll, it was hard to tell whether the California cowboy was for real.

The verdict was clear by his third album, Buenas Noches from a Lonely Room, whose key cycle of songs is a classic murder tale that echoes the pride, heartbreak, betrayal, and vengeance of the age-old hillbilly experience.

[108] Darryl Smyers of the Dallas Observer wrote that "With his absurdly large hat and Flying Burrito Brothers fashion sense, Yoakam was championed by a surprising mix of punks, rockabilly hounds, and hard-core honky-tonkers.

[117] Longtime producer and guitarist Pete Anderson filed a lawsuit against him in 2004, stating that he had breached an oral contract by failing to perform a number of concert dates in mid-2002.

[118] Yoakam and Anderson settled the lawsuit out of court, with the former stating that some of the financial issues stemming from these concerts were due to money lost in the commercial failure of South of Heaven, West of Hell.