Best Dwight Yoakam Songs: 10 Essential Modern Country Classics

9: Little Sister (from ‘Hillbilly Deluxe’, 1987)

A high-energy cover of Elvis Presley’s 1961 rocker, Little Sister was the lead single from Dwight Yoakam’s second studio album, Hillbilly Deluxe, and shows Yoakam having a great deal of fun paying tribute to the “King Of Rock’n’Roll”. Putting a country spin on Presley’s original, Yoakam makes the song his own as he yodels its mischievous lyrics. Peaking at No.7 on the US Hot Country Singles chart, the song’s twangy guitar licks and bluesy guitar solo kicked open the barn door for a new generation to appreciate the enduring charm of vintage honky-tonk and rockabilly.

8: I Sang Dixie (from ‘Buenas Noches From A Lonely Room’, 1988)

Belonging to country music’s rich tradition of mournful storytelling, I Sang Dixie is a haunting tale from Yoakam’s third album, detailing the downward spiral of a dying alcoholic (“I sang Dixie/As he died/People just walked on by/As I cried”), sung with pathos from a man who has been teetotal his whole life. Producer Pete Anderson was always fond of the song, later explaining that they’d held it back until the time was right. “I Sang Dixie I’d always set a little bit aside, because I thought it was his best song,” he said. “I didn’t want to put it on the first or even the second album, because I thought this is a No.1 record.” He was right. One of the saddest ballads among the best Dwight Yoakam songs, I Sang Dixie peaked at No.1 on the US Country Singles chart.

7: Little Ways (from ‘Hillbilly Deluxe’, 1987)

Paying homage to his biggest musical influence, Buck Owens, Dwight Yoakam delivers a pitch-perfect tribute to the country legend’s classic style on Little Ways. As engineer and backing vocalist Dusty Wakeman explained, “They were trying to capture a sound in the studio, that Bakersfield sound, an updated version.” Boasting bright fiddles and a sprightly tempo, the song was released as the second single from Yoakam’s second album, Hillbilly Deluxe, in June 1987. Thanks to its embrace of the no-frills, stripped-down honky-tonk aesthetic, Little Ways became yet another Top 10 hit on the Billboard country chart and saw Yoakam proudly pick up the baton from his songwriting hero, bringing the Bakersfield sound roaring back to life.

6: Ain’t That Lonely Yet (from ‘This Time’, 1993)

With string arrangements scored by Paul Buckmaster – best known for his work with Elton John and on David Bowie’s Space Oddity – Ain’t That Lonely Yet is one of the best Dwight Yoakam songs for capturing the heartache of a lovesick country boy. Co-written by Kostas Lazarides and James House, the song spins the tale of a heartbroken man desperate to win back his ex-lover, its lyrics weaving a particularly poetic web (“Once there was this spider in my bed/I got caught up in her web of love and lies”). As House explained to American Songwriter magazine: “Kostas asked me if I was going to get back together with my estranged girlfriend, and I said, ‘I ain’t that lonely yet,’ and we looked at each other and said, ‘Let’s write that.’” After peaking at No.2 on the US country chart, Ain’t That Lonely Yet would go on to win Dwight Yoakam his first Grammy, for Best Country Vocal Performance, Male, in 1994.

5: Streets Of Bakersfield (with Buck Owens) (from ‘Buenas Noches From A Lonely Room’, 1988)

Joining forces for a duet with country legend Buck Owens, in order to revisit Owens’ cover of Homer Joy’s Streets Of Bakersfield, this was the moment Dwight Yoakam finally scored his first country chart-topper. “I always thought it was a big song and that’s why I harangued Dwight to record it,” Owens said in a 1992 interview. “To be part of a No.1 song years later was a great experience.” Combining Yoakam’s skill for updating vintage honky-tonk with Owens’ hard-won gravitas, the song is pure country fun. Topped off with a jaunty use of accordion, it saw the elder statesman of country music pass the baton to Yoakam as the proud inheritor of Bakersfield’s rough-hewn charm.

4: Honky Tonk Man (from ‘Guitars, Cadillacs, Etc., Etc.,’ 1986)

There’s no denying it: Dwight Yoakam’s energetic cover of Johnny Horton’s 1956 hit Honky-Tonk Man was a milestone for contemporary country music. Issued as Yoakam’s debut single, in January 1986, it became the first country song to air on MTV, peaking at No.3 on the US Hot Country Singles chart and exposing a whole new generation to the genre. “I have kids come up to me all the time and say, ‘I never really liked country music before,’” Yoakam told Song Hits magazine the following year. “And I always tell them the same thing: ‘That’s probably because you’ve never had it presented to you in a way that you could like or that you’ve even heard real country music before.’” Kicking off Yoakam’s neo-traditionalist crusade, Honky Tonk Man stood in stark contrast to pop-leaning “urban cowboy” fodder, and its breakout success on MTV undoubtedly changed the face of country music for years to come.

3: A Thousand Miles From Nowhere (from ‘This Time’, 1993)

Cloaking his heartbreak in an upbeat melody, A Thousand Miles from Nowhere was written by Dwight Yoakam after a romantic relationship came to an end (“I’m a thousand miles from nowhere/Time don’t matter to me/’Cause I’m a thousand miles from nowhere/And there’s no place I want to be”). Released as the second single from his fifth studio album, This Time, this plaintive lament for lost love went on to peak at No.2 on the Billboard country chart and is fondly regarded by fans as one of the best Dwight Yoakam songs. “I think it sounds pretty majestic and melodic,” producer Pete Anderson later told Guitar Player magazine. “I still love how it sounds. I think I came up with a great slide part that really took things to another level.” Evoking classic country themes of loneliness and heartache for a modern audience, A Thousand Miles From Nowhere is one of Dwight Yoakam’s greatest songwriting triumphs.

2: Guitars, Cadillacs (from ‘Guitars, Cadillacs, Etc., Etc., 1986)

The second single from Dwight Yoakam’s breakthrough 1986 album, Guitars, Cadillacs is enough to get anyone’s motor running. Merging classic honky-tonk with 50s rockabilly and a forward-looking production style characterised by twanging guitar hooks, the song peaked at No.5 on the US Hot Country Singles chart, thanks in part to an effortlessly cool promo video. Directed by manager Sherman Halsey, the clip hit all the touchpoints of rural North America’s cultural heritage, as a denim-clad Yoakam swung his hips in a car garage (“Yeah, my guitars, Cadillacs, hillbilly music,” he sings, “is the only thing that keeps me hanging on”). “That Cadillac meant you made it,” Yoakam told Country Music Television in 1986. “If you came out of the hills of Kentucky and you had a Cadillac, you were somebody.” By wrapping rock’n’roll nostalgia in an irresistibly catchy honky-tonk bop, Guitars, Cadillacs continued Yoakam’s neo-traditionalist takeover of MTV, dragging country music into a whole new era.

1: Fast As You (from ‘This Time’, 1993)

Easily one of Yoakam’s most popular songs, Fast As You saw the singer cross over to the US Hot 100 for the very first time, courtesy of a rollicking guitar riff reminiscent of Roy Orbison’s Pretty Woman. Meeting with extraordinary success to propel its parent album, This Time, to sell over 3.2 million copies, it remains a firm fan favourite, with more than 70.6 million Spotify streams to its name. “Fast As You was an intelligent lyric written to an uptempo groove, which is a pretty lethal combination,” Pete Anderson said. “Wow! That was a big rocket ship for that record.” Marking the peak of Dwight Yoakam’s meteoric rise as a country music trailblazer who brought old-school honky-tonk back into fashion, Fast As You outpaces the competition to top our list of the best Dwight Yoakam songs.

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