Dwight Yoakam

The Best Dwight Yoakam Songs

July 11, 2022 4:21 pm GMT
Last Edited June 19, 2023 3:03 pm GMT

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When Dwight Yoakam first started to show up in LA in the early 80s, he was a mass of contradictions.

A Kentucky boy in the City of Angels playing hardcore honky tonk to an audience of punks who did not know a Nudie suit when they saw one, and nor did they care to. So it went on, until a decade later he was the biggest country star in the world.

36 years and 24 albums in, Yoakam's music is forward-looking and traditional at the same time.

Here’s our best Dwight Yoakam songs list.

Reprise | 2001

No Future In Sight

In 2001, having achieved little success as an actor, Dwight decided to write, produce, score and star in his own Western vehicle South of Heaven West Of Hell.

It was a failure on nearly every level, a catastrophic mistake which resulted in the singer losing his Malibu estate, the repayment of the accrued debts having a profound effect on his subsequent career.

The soundtrack album was brilliant though, with collaborators including Mick Jagger and ZZ Top’s Billy Gibbons. This is the best track from it; seven minutes of burnished desert blues that shines like a steel guitar in the sun.

Reprise | 2000

Readin', Rightin' Rt.23 (Acoustic)

The original version was great, but this stripped-down version - from the turn of the century unplugged effort dwightyoakamacoustic.com - is the one.

Driven along by an impassioned vocal and an even greater rhythm guitar, this is solo Dwight at its peak.

Reprise | 1988

Buenas Noches From A Lonely Room (She Wore Red Dresses)

The climax of the tremendous neo-noir suite of songs that form the first half of this similarly titled 1988 album. It does not end well.

Concord | 2016

I Wouldn't Put It Past Me

Dwight’s most recent album, 2016’s Swimmin’ Pools, Movie Stars.. was his first in a bluegrass style, and very good it was too.

The cream of the crop from the record is this redo of a 1998 original.

Warner | 2015


We're reversing into the future now if you can believe it.

It’s back to 1966 for the chiming 12 strings of the Beatles and the Byrds, and back to 1963 for the drum part from Be My Baby for this gem from 2015’s Secondhand Heart.

A revved-up Dwight channels a Joshua Tree-era Tom Petty, produced by Phil Spector, to tremendous emotional effect.

Warner Nashville | 2012

Long Way To Go

Three years previously and re-signed to his original label Warner, Yoakam had revitalised his career with the tremendous 3 Pears album.

It was a vibrant optimistic affair personified by this gentle hymn to perseverance.

Reprise | 1993

Ain't That Lonely Yet

Every now and then it turns out that an artist’s best work is also their most popular, and so it was with Dwight’s 1993 album This Time.

It remains both his biggest seller and the album you should get if you only want one Yoakam record, cementing a unique sound that moved beyond the sum of its parts to become Dwight alone.

5 of its 11 songs were massive hits, and this was the first of them. A tight little Kostas/James House number that won Dwight a vocal Grammy, all while warming up the country audience for the tsunami to come.

Reprise | 1998

Things Change

1998 saw the release of A Long Way Home, Dwight’s first complete album of self-penned material.

Mostly written while hanging around on the Texas set of Richard Linklater’s The Newton Boys, the new songs were a return to the more straightforward country music of Dwight’s earlier records, none more so than this.

Reprise | 1995

Sorry You Asked?

From 1995’s Gone - the album that started Yoakam’s commercial if not aesthetic decline - this contains a masterpiece of a lyric.

It's nothing less than transcribed conversation; a trick that’s much, much harder to pull off than it sounds, especially when it’s also dead pan hilarious. Is this a verse or a remark?

"Okay we both have the tendency to overreact / so I can't really tell you who's at fault / but there were certain third parties, well her sister for one / who helped bring our reconciling to a drop-dead halt".

Reprise | 1988

I Sang Dixie

Written after a home state visit to Kentucky from California, 'I Sang Dixie' is an unashamed heartstring tugger.

Our man finds a homeless southern compatriot dying on the streets of LA and - yes – sings Dixie to comfort him in his final moments.

It was in Yoakam’s live set for nearly a decade before he recorded it, strategically holding it back until he felt it would be most effective. Good call – it became Dwight’s second No. 1 in 1988.

Warner | 1997

Come On Christmas

Often the last resort of scoundrels, ne’er do wells and panic-stricken former pop stars, one rather suspects that Dwight approached his Yuletide offering in the spirit of a performance art project.

Most of the album is expectation-killing stuff - like Away In A Manger, Silent Night and Silver Bells - but that doesn’t account for this, one of the two Yoakam originals on the record and so comically morose that he surely cannot be serious.

Or can he? Either way, it’s a cracker (sorry).

Reprise | 1990

It Only Hurts When I Cry

Sometimes it’s just about classic country songwriting. Especially when you write with Roger Miller.

Warner | 1986

Guitars, Cadillacs...

The title track from his 1984 debut EP on Oak Records, this was the first stone-cold Dwight classic; ancient and modern at once.

It was the song that got Yoakam signed to a major label and showed LA’s punk community a vision of a different future when he started showing up on live bills with X and The Blasters.

Reprise | 1999

Crazy Little Thing Called Love

Dwight has always had a fantastic line in covers, from the obvious (Streets Of Bakersfield with Buck Owens) to the off-the-wall (a bluegrass Purple Rain recorded on the day Prince died, anyone?)

This one stands high above all of them. If you ever had a suspicion that Freddie Mercury might have written a hillbilly classic, well here’s the proof…

Reprise | 1993

A Thousand Miles From Nowhere

Again from It’s Time, this is Dwight in excelsis.

Rippling guitar lines roll out from his greatest melody, it's his most heartbreaking lyric and it contains a gorgeous extended coda inspired by the last few minutes of Derek & The Dominos’ Layla.

It nearly didn’t make the album, as both Yoakam & producer/collaborator Pete Anderson felt that it might be too experimental. In the end, good sense prevailed and, as Anderson later remarked, it was a key staging point in Dwight’s career:

“I wanted to get to a point where we made Dwight Yoakam music. Whatever Johnny Cash was, Johnny Cash made Johnny Cash music. Was it country, was it folk, was it Americana, was it rockabilly? It was Johnny Cash music. Kenny Rogers, for better or worse, made Kenny Rogers music. I wanted Dwight to be in that stratosphere“.

After this, he was.


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Written by Mark Hagen
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