Dwight Yoakam's 25 Greatest Songs

*This article was originally published on The Word's original website in 2014

by Julian Spivey

1. The Back of Your Hand

Writer: Gregg Lee Henry
Album: Population Me
Year: 2003

What? You’ve never even heard of “The Back of Your Hand,” you say? It was a not so warmly received single from Dwight Yoakam’s 2003 album “Population Me” that most novice Yoakam fans may never have heard, but it’s supremely beautiful in its tragedy and Yoakam’s mournful twang turns it into one of the most crushing songs I’ve ever heard performed. The lyrics and the brilliant reading of them by Yoakam will truly tear at the corners of your soul and the complexity of them is frankly unusual for a Yoakam tune. Uniquely enough Yoakam is a singer who acts and Gregg Lee Henry, the songwriter, is an actor who sings and writes beautiful songs. No wonder the song’s acting metaphors ring so true.    

2. Guitars, Cadillacs

Writer: Dwight Yoakam
Album: Guitars, Cadillacs, Etc., Etc.
Year: 1986

“Guitars, Cadillacs” is the Dwight Yoakam song, and the one that I believe most will always associate him with and would likely agree upon as his best (“The Back of Your Hand” is a personal preference for me). “Guitars, Cadillacs” was Yoakam’s second single off of his debut album and his first original release. The song must have either been a blessing to those tiring of the Urban Cowboy movement of the early ‘80s or a little bit of a “what-the-hell-is-going-on-here?” moment by those not in tune with the rockabilly, country-rock sound of the late ‘50s. “Guitars, Cadillacs” does a terrific job at melding different influences on Yoakam from the raucous rockabilly to that bass line that’s almost ripped from an early ‘60s Buck Owens classic. It was a statement that something new and different had arrived on the country music scene at a time when country music desperately needed it.   

3. Streets of Bakersfield (with Buck Owens)

Writer: Homer Joy
Album: Buenas Noches From a Lonely Room
Year: 1988

“Streets of Bakersfield” must have been the ultimate career highlight for Dwight Yoakam in getting a chance to sing about not only his hometown, but with his hero Buck Owens. This song penned by Homer Joy is the perfect representation of the Bakersfield Sound, popularized in the ‘60s by Dust Bowl transplants like Owens and Merle Haggard. It’s a sound that greatly influenced Yoakam and this magical duet is a way of him paying tribute to it. I also love the message contained within the lyrics of this song … don’t judge people without getting to know them first. Yoakam has always been an outsider to mainstream country music and this song represents that better than just about any he’s recorded.

4. I Sang Dixie

Writer: Dwight Yoakam
Album: Buenas Noches From a Lonely Room
Year: 1988

Dwight Yoakam is no stranger to absolutely crushing songs, most having to do with heartache or the betrayal of a love, but his ballad of a dying Southerner transplanted to the lonely in their nonstop busyness streets of Los Angeles is his most heartbreaking track. The narrator of the song is horrified by this old man being ignored by passersby, left alone to die in the hustle and bustle of it all, so he stops to comfort the man by singing the Southern anthem “Dixie.” It’s a poetically beautiful piece of not only one longing for home toward the very end, but also of a little bit of humanity alive in a place devoid of it. 

5. A Thousand Miles From Nowhere

Writer: Dwight Yoakam
Album: This Time
Year: 1993

“A Thousand Miles From Nowhere” is one of the finest in a long line of Dwight Yoakam songs about being treated cruelly by a lover and attempting to rid oneself from that pain and torture. This song contains some of the most heartbreakingly torturous lyrics Yoakam ever put to paper with lines like: “I’ve got bruises on my memory/I’ve got tear stains on my hands/And in the mirror there’s a vision/Of what used to be a man.” His plaintive, almost crying “Oh I”s scattered throughout the song really hit home the mournful balladry of the piece. It’s truly one of Yoakam’s finest vocals – and has gotten him nominated for Grammy Awards on two separate occasions: for his live performance on 1996’s “Dwight Live” and the acoustic version from his 2000 album “dwightyoakamacoustic.net.” 

6. Little Ways

Writer: Dwight Yoakam
Album: Hillbilly Deluxe
Year: 1987

“Little Ways” is Dwight Yoakam doing his best Buck Owens impression and it works effortlessly. Just listen to the enunciation of the first three words of the song “You’ve … got … your” and take a listen to the “I’ve … got … a …” from Owens’ 1964 hit “I’ve Got a Tiger By the Tail.” The opening of “Little Ways” could easily pass for Owens. Yoakam does heart beaten into the ground heartbreak ballads better than just about anybody else with his mournful twang that makes everything sound painstakingly rough. There’s not a whole lot of difference between some of Yoakam’s mournful ballads like this, “Ain’t That Lonely Yet” and “You’re The One” other than different lyrics, but “Little Ways” with its Owens homage probably stands out at the top.

7. The Heart That You Own

Writer: Dwight Yoakam
Album: If There Was a Way
Year: 1990

Trying to pick out the most devastating Dwight Yoakam lyric would be like trying to decide which one of your kids is your absolute favorite … it’s not easy. However, I think I may have pinpointed which lyric that may be (at least for this time and place) and it comes from his 1992 single “The Heart That You Own.” “I pay rent on a rundown place/There ain’t no view, but there’s lots of space/In my heart, the heart that you own/I pay the rent, pay it right on time/Baby, I pay you every single dime/For my heart, the heart that you own.” That’s one of the saddest things I’ve ever heard, especially with the longing croon in which Yoakam delivers it. It’s a Merle Haggard-esque bit of songwriting and performing if I’ve ever heard it, which is to truly say it’s utterly brilliant in its melancholy. This song truly should’ve been a bigger hit than it was (only reaching number 18 on the country chart), but maybe its throwback appeal hurt it among the modern audience.      

8. Ain’t That Lonely Yet

Writer: Kostas & James House
Album: This Time
Year: 1993

“Ain’t That Lonely Yet” is a heartbreak ballad like many of Dwight Yoakam’s greatest songs, but one with a nice little twist and a quite powerful one, at that. The narrator’s had his heart broken by his lover, but now she realizes her mistake and wants him back, but he’s not about to fall for her game again. The phrase “ain’t that lonely yet” just hits home that it’s going to be one cold day in hell before he’s ready to accept her again. The ex-lover as a web-spinning spider metaphor in the second verse of the song is also one of the finest bits of poetics in Yoakam’s discography. 

9. Fast As You

Writer: Dwight Yoakam
Album: This Time
Year: 1993

“Fast As You” is Dwight Yoakam at his most suave, boastful and sexiest. Certainly the exact opposite attitude of all of the weepers he has that appear on this very list – and yet the inspiration for this song is basically the same as the weepers. However, this time Yoakam isn’t crying or moaning over being treated poorly by his love, but is bound and determined to keep up in the treachery of love without bounds. It’s an eye-for-an-eye relationship song. “Fast As You” is Yoakam at his most rollicking and unabandoned and must be one of the performances to see from him live in concert. 

10. I Want You to Want Me

Writer: Rick Nielsen
Album: Tomorrow’s Sounds Today
Year: 2000

Dwight Yoakam’s cover of the popular 1977 Cheap Trick rock song “I Want You To Want Me” is one of his coolest covers and the one cover I’ve ever heard that is world’s better than the original version. Granted I’m not too keen on cheesy arena rock bands like Cheap Trick, but I think Yoakam is able to strip away the cheesiness of this track and turn it into something that’s more yearning for love than begging for it. I believe this yearning comes out in Yoakam’s one-of-a-kind twang that only he seems truly capable of conjuring. That one difference is key to the song and truly makes Yoakam’s version the definitive version for me.

11. You’re The One

Writer: Dwight Yoakam
Album: If There Was a Way
Year: 1990

“You’re The One” is like many of Dwight Yoakam’s heartbreak ballads, but with a nice bit of screw you thrown in to it for a twist. The narrator of the song is talking about all of these truly horribly things that his lover has done to him, but reveals that she’s been repaid with a little bit of her own medicine. Yoakam’s truly unique drawling voice fits the tone and mood of this song so well and that makes both the narrator’s pain and his unflinching “I don’t care” attitude when the tables are turned on his ex stand out so brilliantly. 

12. It Only Hurts Me When I Cry

Writers: Dwight Yoakam & Roger Miller
Album: If There Was a Way
Year: 1990

You can just tell by listening to the lyrics of Dwight Yoakam’s “It Only Hurts Me When I Cry” that Roger Miller played a huge role in the writing of it. In fact, this was one of the very last songs the legendary Nashville songwriter penned before his death in 1992 at the early age of 56 from lung and throat cancer. Just the phrasing in the chorus: “The only time I feel the pain/Is in the sunshine or the rain/And I don’t feel no hurt at all/Unless you count when teardrops fall/I tell the truth ‘cept when I lie/It only hurts me when I cry” is straight out of Miller’s brilliant playbook. Also, out of the legend’s playbook is how this song can be so almost peppy in its sadness. It must have been such an honor for Yoakam to pen a song with one of the genre’s greatest songwriters of all-time.  

13. Carmelita (with Flaco Jimenez)

Writer: Warren Zevon
Album: Partners
Year: 1992

“Carmelita” is one of my favorite covers by Dwight Yoakam and was initially done for famed Tejano accordionist Flaco Jimenez for his 1992 album “Partners,” and can be found on Yoakam’s anthology set “Reprise Please Baby: The Warner Bros. Years.” The song was written and recorded by the terrific singer-songwriter Warren Zevon for his 1976 self-titled album and is about a man wanting to be consoled by his girl while having a bad time being strung out on heroin, a rather bold choice for Jimenez and Yoakam to cover. With all due respect to Zevon, who’s a personal favorite of mine, I believe this version thanks to Yoakam’s yearning delivery and Jimenez’s Latin flavor is the perfect version of “Carmelita.”

14. Honky Tonk Man

Writers: Johnny Horton, Tillman Franks & Howard Hausey
Album: Guitars, Cadillacs, Etc., Etc.
Year: 1986

I’ve long said that nobody does covers like Dwight Yoakam and this was the very first sign of that. Many covers are almost too loyal to the originals for their own good, but Yoakam always makes a cover sound like a Dwight Yoakam song and does so while also somehow remaining true to the original’s roots. His first single back in 1986 was cover of Johnny Horton’s 1956 single “Honky Tonk Man.” Horton’s version is classic, but doesn’t have that certain cool swagger that Yoakam gives it. The song went to number three on the charts and introduced the world to a guy who was ready to do traditionalism his own way.  

15. Suspicious Minds

Writer: Mark James
Album: Honeymoon in Vegas (Movie Soundtrack)
Year: 1992

“Suspicious Minds” is one of the coolest and best songs that Elvis Presley ever recorded and Dwight Yoakam being the incredibly cool cat that he is and supreme Elvis fan cut this tune for the soundtrack to the 1992 movie “Honeymoon in Vegas” and in some ways seemed to have one-upped even the King of Rock ‘n’ Roll (not bad, considering Rolling Stone ranked Elvis’ version as one of the 100 greatest songs of all-time). It’s a song that just fits the Dwight Yoakam modus operandi – narrator trapped in a less than ideal relationship in which trust issues are key. The best Yoakam version of this song appears on the terrific anthology set “Reprise, Please, Baby” (2002), in which 22 of the 25 songs on this list appear. Elvis is likely one of the most covered artists of all-time and to this date this is the very best cover of an Elvis song I’ve ever heard.    

16. Pocket Of a Clown

Writer: Dwight Yoakam
Album: This Time
Year: 1993

The shuffling tune “Pocket of a Clown” has some truly great imagery and is probably one of Dwight Yoakam’s best written songs with lines like: “Inside the pocket of a clown/Is a sad place to hang around/Just watching smiles turn into frowns/Inside the pocket of a clown.” And, then Yoakam’s tailored worn pining on the chorus just hits home the somberness of the whole thing. It’s amazing to me that the song wasn’t more of a hit than it was; failing to reach even the top 20 in 1994.

17. Rapid City, South Dakota

Writer: Kinky Friedman
Album: Why The Hell Not … The Songs of Kinky Friedman
Year: 2006

“Rapid City, South Dakota,” a Kinky Friedman song that Dwight Yoakam covered for a Freidman tribute album, is an unusual Yoakam song for a couple of reasons. It’s unusual because it’s a story song, which is something you don’t typically get from Yoakam, more in tune with heartbreak ballads and honky tonk swingers. This story aspect of “Rapid City, South Dakota” is part of what makes it so intriguing. The topic of the story is what might have made it controversial had it been released as a single to country radio. The narrator of the story, “a ragged kid with overalls” who’s escaping Rapid City, South Dakota mighty fast with the girl he impregnated left behind. Not to worry though, he’s left her with the name of a doctor in Chicago that can take care of the issue. Friedman called the song the “first pro-choice country song,” which makes it a rather unique and brave cover for Yoakam. The emotions of the story come out brilliantly in Yoakam’s twangy delivery.   

18. Turn It On, Turn It Up, Turn It Loose

Writer: Kostas & Wayland Patton
Album: If There Was a Way
Year: 1990

“Turn It On, Turn It Up, Turn It Loose,” from 1990’s “If There Was a Way,” is quite possibly Dwight Yoakam’s most upbeat heartbreak song as the narrator opts to dance his blues away with a stranger in a honky tonk rather than crying in his beer. When you do as many heartbreakers as Yoakam does it’s probably hard to put a new or different spin on the topic, but this song co-written by Kostas and Wayland Patton does the trick perfectly. The song includes one of the best instrumental interludes of any Yoakam song, as well, featuring Scott Joss’ mandolin solo after the first chorus. The Buck Owens reference in the song’s second verse surely must have been a key in Yoakam choosing this song.

19. This Drinkin’ Will Kill Me

Writer: Dwight Yoakam
Album: Hillbilly Deluxe
Year: 1987

Dwight Yoakam’s “This Drinkin’ Will Kill Me” is a song that I’ve heard performed in many different variations from its original album appearance on “Hillbilly Deluxe,” the 1981 demo version from the “Guitars, Cadillacs, Etc., Etc.” Deluxe Edition reissued in 2006 and the acoustic version from “dwightyoakamacoustic.net” … and it’s sounded perfect every single time. Based on the fact that it was one of his 1981 demos, five years before his debut album, this must be one of Yoakam’s oldest songs and it shows that he had a rare and unique talent at an early age. “This Drinkin’ Will Kill Me” includes one of Yoakam’s best and countriest choruses with the supremely written: “Death can come from this broken heart/Or it can come from this bottle/So why prolong the agony/Hey, bartender, I think I’ll hit the throttle.” Despite liking all the variations of this song, I do believe that the best performance is from his 1981 demo session, it’s a little less chaotic than the album version and a little more emotional than the acoustic take.

20. Crazy Little Thing Called Love

Writer: Freddie Mercury
Album: Last Chance for a Thousand Years: Dwight Yoakam’s Greatest Hits from the 90’s
Year: 1999

As mentioned on number 15 above, and number 21 below, Dwight Yoakam is quite the Elvis Presley fan. “Crazy Little Thing Called Love” is not an Elvis song, but rather a Queen song that became the group’s first American number one single in 1980. However, “Crazy Little Thing Called Love” is a song that I always felt sounded like it could have been an Elvis song in its rockabilly style, and upon doing some research have found out that Queen frontman Freddie Mercury did in fact write it as a tribute to the late Presley. I think it’s this Elvis-esque quality of the tune that enamored Yoakam and led him to cut it himself. It’s another one of those effortlessly cool Yoakam cover songs that some could argue is, in fact, better than the original.

21. Little Sister

Writers: Doc Pomus & Mort Shuman
Album: Hillbilly Deluxe
Year: 1987

Buck Owens is likely Dwight Yoakam’s biggest musical influence and hero, but you can tell throughout the years that Yoakam is a huge fan of the King of Rock ‘n’ Roll Elvis Presley. Yoakam has recorded numerous Elvis songs over the years like “Suspicious Minds,” “Mystery Train” and this song, “Little Sister,” which Elvis took to number five on the Billboard Top 40 chart in 1961. With no disrespect intended toward The King, Yoakam tends to find a way to spice up and improve on Presley’s classics and this is prime example. Some people would probably find it mighty hard to out sexy Elvis Presley, but Yoakam manages to do just that by infusing some serious swagger few but him could muster.  

22. The Late, Great Golden State

Writer: Mike Stinson
Album: Population Me
Year: 2003

Like “The Back of Your Hand,” at number one on this list, “The Late, Great Golden State” is a little played single from Dwight Yoakam’s 2003 album “Population Me,” that is frankly a hidden classic from Yoakam’s discography. It’s a great representation of the California sound not only represented by the Bakersfield Sound, but also by California rock groups like Creedence Clearwater Revival. I think the line from the song “I ain’t old, just out of date in the late, great Golden State,” despite being written by someone else, is a terrific line for this time in Yoakam’s career were he couldn’t care less if were played on country radio, but is content to record the kind of music he wants to record.    

23. A Heart Like Mine

Writer: Dwight Yoakam
Album: 3 Pears
Year: 2012

Dwight Yoakam’s latest album 2012’s “3 Pears,” which broke the record for most weeks at number one on the Americana music chart, proved just how unique of an artist Yoakam truly is mixing different musical styles into one to create one of the best received “country” albums of that year. “A Heart Like Mine” is the standout track from the album and sounds incredibly retro, like it could have been a hit song on Top 40 radio in the ‘60s. It’s Bakersfield Sound meets psychedelic rock and it produced one of the most unique tracks Yoakam has recorded.   

24. Close Up the Honky Tonks 

Writer: Red Simpson
Album: Dwight Sings Buck
Year: 2007
 
You knew it was only going to be a matter of time before Dwight Yoakam recorded a complete tribute album to his Bakersfield music idol Buck Owens. Yoakam released “Dwight Sings Buck” the year after the Country Music Hall of Famer passed away in 2006 featuring some of the icon’s biggest hits like “Act Naturally” and “Together Again,” but the best cover off of the album proved to be the lesser known “Close Up the Honky Tonks,” written by Red Simpson and featured on Owens’ 1964 “Together Again” album, but not released as a single. Yoakam turns the plaintive song about a man losing his love to the bright lights and hot action of the local honky tonk into a six-plus minute epic equipped with some of the finest steel guitar you’ve heard in years.
 
25. Try Not to Look So Pretty 

Writers: Dwight Yoakam & Kostas
Album: This Time
Year: 1993
 
“Try Not to Look So Pretty” is one of those quintessentially heartbreaking Dwight Yoakam ballads. It’s beautiful in its simplicity of a man trying to steer clear of a wily, dangerous woman because he knows she’s bad for him, but she’s just too darn pretty to turn down. It’s Merle Haggard-esque in both its performance and lyrical content. It’s also solid proof that Yoakam would have been just as popular in the ‘50s and ‘60s as he was in the ‘80s and ‘90s. 

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