Let’s be real: Willie Nelson is an American treasure. He’s a guy who can go from hanging out in the White House (no matter who is living there at any given moment) one night to a honky tonk the next. He’s collaborated with country’s biggest stars, as well as rock, hip-hop, jazz and blues icons. Today, he’s releasing his 72nd album, A Beautiful Time and he’s celebrating his 89th birthday. We’ve decided to celebrate him, by looking back on his 89 best songs from the early ’60s to today.
89. The Willie Nelson Family – “I Saw The Light” from ‘The Willie Nelson Family’ (2021)
ShareThe ‘Family’ album sees Willie collaborating with his sons Lukas (who fronts the rock band Promise of the Real) and Micah (who fronts his own band, Insects Vs. Robots), his daughters Paula (a solo artist) and Amy (of the group Folk Uke) and his late sister Bobbie Nelson, who played piano in his band for decades. “I Saw The Light” is a timeless gospel song, but it’s given new gravitas when Willie sings it with his kids and sister.
88. The Highwaymen – “The Devil’s Right Hand” from ‘The Road Goes On Forever (1995)
ShareThe Highwaymen is arguably country music’s most celebrated supergroup. It featured Willie, Johnny Cash, Waylon Jennings and Kris Kristofferson. This song, from their third and final album, is a cover of outlaw country icon Steve Earle’s classic; Jennings had previously covered it on his own. A warning about firearms, the lyrics include “My very first pistol was a cap and ball Colt /Shoots as fast as lightnin' but it loads a might slow /It loads a might slow, and soon I found out /It'll get you into trouble but it can't get you out.”
87. Snoop Dogg featuring Willie Nelson – “Superman” from ‘Doggumentary’ (2011)
ShareWe all know what Snoop and Willie have in common, so it’s not hugely surprising that they’d get together to collaborate. But would a song featuring the two be a stunt, or worse, a car crash? “Superman” turned out pretty well, actually, which is why we included it here. It’s not a hip-hop song: it’s just Willie singing and strumming guitar, Mickey Raphael on harmonica and Snoop singing his own verse. Both men sing about the hard realization that they’re not invulnerable anymore.
86. “Border Song” from ‘Restoration: The Songs of Elton John and Bernie Taupin’ (2018)
ShareAn early Elton John classic that has been covered by Aretha Franklin and Eric Clapton, among many others. Willie’s vocals don’t match those singers, and he does strain a bit here, but it’s moving to hear him sing, “Holy Moses, let us live in peace, let us strive to find a way to make all hatred cease/there’s a man over there/what’s his color, I don’t care/He’s my brother, let us live in peace.”
85. Kacey Musgraves featuring Willie Nelson – “Are You Sure?” from ‘Pageant Material’ (2015)
ShareA hidden track on Musgraves’ ‘Pageant Material’ album, it shows that her love of Willie is more than just lip service. “Are You Sure?” is a pretty obscure track from Nelson’s third album, 1965’s ‘Country Willie: His Own Songs.’ But Musgraves was praising the song in 2013 on social media, writing, “Willie Nelson’s ‘Are You Sure’ — two minutes and 13 seconds of the realest s— you’ll ever hear. Never gets old. Thank you, Willie.”
84. Chris Young featuring Willie Nelson – “Rose In Paradise” from ‘The Man I Want To Be’ (2009)
ShareA cover of a 1987 Waylon Jennings song; Willie’s voice somehow works perfectly with Young’s, bringing this classic to a new generation.
83. Kenny Chesney featuring Willie Nelson – “That Lucky Old Sun (Just Rolls Around Heaven All Day)” from ‘Lucky Old Sun’ (2008)
ShareThe song was popularized by jazz great Louis Armstrong in 1949, and was later recorded by Ray Charles in 1963. Nelson himself covered it in the ‘70s, but there’s a sweetness to this version, which sees Willie in his 70s, singing “Fuss with my woman, toil for my kids/Sweat till I'm wrinkled and gray/While that lucky old sun got nothin' to do/But roll around heaven all day.” You can just picture Willie and Kenny singing it with their guitars on a beach somewhere.
82. “He Was A Friend Of Mine” from the ‘Brokeback Mountain’ soundtrack (2005)
ShareA cover of a traditional blues song from the 1930s, it definitely took a different meaning when used in ‘Brokeback Mountain’: “He was a friend of mine/Every time I think of him/I just can't keep from cryin'/'Cause he was a friend of mine.”
81. U2 featuring Willie Nelson and Mickey Raphael – “Slow Dancing” (B-side of “If God Will Send His Angels” CD single, 1997)
Share80. “Bird On A Wire” from ‘Tower Of Song – The Songs Of Leonard Cohen’ (1995)
ShareLegendary singer/songwriter Leonard Cohen wasn’t a country artist, but he said that he felt that “Bird On A Wire” is, in fact, a country song. Indeed, Willie’s fellow Highwayman Johnny Cash also covered this song, while Kris Kristofferson allegedly told Cohen that he was going to put the first few lines on his gravestone. And Willie sings them as good as anyone ever has: “Like a bird on the wire/Like a drunk in a midnight choir/I have tried in my way to be free.”
79. Frank Sinatra featuring Willie Nelson – “A Foggy Day” from “Duets II’ (1994)
ShareSinatra’s ‘Duets’ album brought him back to the pop charts at the age of 78 in 1993, and his team struck while the iron was hot, releasing the follow-up in ‘94. Sadly, Nelson and Sinatra didn’t actually record this song together: they laid down their vocals at separate sessions. Still, Willie’s excitement about singing with Sinatra is clear on the song; he’d later pay tribute to the man on his albums ‘That’s Life’ (2021) and ‘My Way’ (2018).
78. “Our Song” from ‘First Rose Of Spring’ (2020)
ShareWritten for Willie by Randy Houser, along with Allen Shamblin and Mark Beeson. It’s a beautiful love song, about a man who meets a woman, falls in love and everything changes. And then: “The last time he saw her /He knew everything had changed /He said goodbye and let the tears fall like rain /On the first rose of spring.” Whew: that’s heavy.
77. “Delete and Fast Forward” from ‘God’s Problem Child’ (2017)
ShareCo-written by Willie and producer Buddy Cannon. It sounds like vintage Willie but the lyrics are decidedly from our era: “Delete and fast-forward the news/The truth is the truth, but believe what you choose/When we blow the whole world back to where it began/Just delete and fast-forward again.”
76. “Last Man Standing” from ‘Last Man Standing’ (2018)
ShareAnother Willie/Buddy Cannon co-write. Willie gets a bit self-conscious about his age, singing, “I don't wanna be the last man standing.” But then, he reconsiders: “On second thought maybe I do/It's getting hard to watch my pals checkout/Cuts like a worn out knife.”
75. “Summertime” from ‘Summertime: Willie Nelson Sings Gershwin’ (2016)
ShareThere are a few elements that have always made Willie stand out from his country peers (other than his very distinctive singing and guitar playing). His Sinatra influence is not really typical in the genre, and that love of Sinatra led him to doing this album of Gershwin songs (most of which, Sinatra had covered). It’s difficult to add your own touch to such iconic songs. “Summertime” dates back to the 1930s, but Willie makes it feel new. And he makes it feel like it’s his song.
74. Willie Nelson and Merle Haggard featuring Jamey Johnson – “It’s All Going To Pot” from ‘Django and Jimmie’ (2015)
ShareFrom Willie and Merle’s sixth album together. Jamey Johnson co-wrote this song with producer Buddy Cannon and Larry Shell, but it sounded like Willie’s words. In the ‘60s, Merle sang “We don't smoke marijuana in Muskogee” in his song “Okie from Muskogee,” but over the decades, Willie may have changed his mind about that. At any rate, the song is a blast.
73. “The Scientist” (single-only release, 2011)// later released as a bonus track on ‘Heroes’ (2012)
ShareOK, who predicted that Willie would cover a Coldplay classic for a Chipotle campaign? It sounds crazy, but it happened. It was for a short animated film called “Back To The Start,” which is still on Chipotle’s YouTube page. The film depicts the life of a farmer as he slowly turns his family farm into an industrial animal factory before deciding that he needed to return to his old methods (“going back to the start”). It was very much the message that Willie has been preaching at Farm Aid for decades.
72. “My Way” from ‘My Way’ (2018)
ShareOne of Sinatra’s most iconic songs, if not *the* most iconic. And, again, Nelson gives the song a new gravitas. Hearing him croon “And now the end is near/And so I face the final curtain” is incredibly poignant. And if anyone deserves to sing “I did it my way,” it’s Willie.
71. “Satan Your Kingdom Must Come Down” from ‘Country Music’ (2010)
ShareWillie has gone down several artistic paths over the decades, but on ‘Country Music,’ produced by T-Bone Burnett (the guy behind the ‘O Brother Where Art Thou’ soundtrack), Willie goes back to the roots of traditional country music. “Satan Your Kingdom Must Come Down” is a 1931 song by South Carolina evangelist Blind Joe Taggart. There are lots of versions of this song, Willie’s is one of the most haunting.
70. “Come Rain Or Come Shine” from ‘American Classic’ (2009)
ShareFrom this dip into the “Great American Songbook,” Nelson worked with producer Tommy LiPuma, whose resume included Barbra Streisand, Miles Davis and Al Jarreau, He used musicians from the jazz world on this album, giving it a very different feel. Not all of the songs on the album worked, but this song, popularized by Billie Holiday and Ray Charles, definitely did.
69. Willie Nelson featuring Calexico – “Senor (Tales of Yankee Power)” from ‘I’m Not There (Music From The Motion Picture Soundtrack)’ (2007)
ShareThis semi-fictional film based on Bob Dylan’s life (or lives) sported a soundtrack of Dylan covers by younger artists like Eddie Vedder, Jack Johnson and the Black Keys. But Willie, backed by Austin rock band Calexico, was one of the highlights. “Senor” is one of Dylan’s weirdest and most mysterious songs, and Willie sings it perfectly.
68. “Bubbles In My Beer” from ‘You Don’t Know Me: The Songs Of Cindy Walker’ (2006)
ShareAs the album title implies, Willie’s 2006 LP was a tribute to songwriter Cindy Walker… and weirdly, it was released just days before her death. She co-wrote this song with the legendary Bob Wills who recorded it with his Texas Playboys in 1947… three years before Hank Williams wrote “There’s A Tear In My Beer.” Which is no shade to Hank: there are thousands of stories to tell about sad nights in bars. And no one sings them better than Willie.
67. “The Rainbow Connection” from ‘Rainbow Connection (2001)
ShareYes, Willie covers Kermit the Frog’s classic from 1979’s ‘The Muppet Movie.’ And yeah, the idea of Willie singing a “Muppet” song sounds like a joke… until you hear it. In the 2000s, Willie explored a number of genres, including children’s music. But in his hands, this song feels like a Willie original.
66. Willie Nelson and Wynton Marsalis – “Bright Lights, Big City” from ‘Two Men With The Blues’ (2008)
ShareA live album recorded at Jazz at Lincoln Center in New York City (Wynton Marsalis’s home turf). The concert, and the live album, prove that the distance between jazz, the blues and country isn’t really that far.
65. “Gravedigger” from ‘Moment of Forever’ (2008)
ShareFrom Willie’s first album with Buddy Cannon; in fact, ‘Moment of Forever’ was co-produced by Cannon and Kenny Chesney. This song is a cover of Willie’s fellow Farm Aid board member, Dave Matthews. It’s one of Dave’s darker songs, and Willie makes it darker still.
64. Willie Nelson featuring Kenny Wayne Shepherd – “Texas Flood” from ‘Milk Cow Blues’ (2000)
ShareWillie dipped into the blues on this 2000 album, and here, he’s joined by one of the big guitar heroes of modern blues, Kenny Wayne Shepherd. This song dates back to the 1950s, but was popularized in the ‘80s by Stevie Ray Vaughan and Double Trouble, and Kenny Wayne’s solo is a tribute to the late legend.
63. “The Harder They Come” from ‘Countryman’ (2005)
Share‘Countryman’ - Willie’s reggae album - was probably Willie’s most ill-advised genre experiment of the 2000s. But this Jimmy Cliff classic, from the 1972 soundtrack of the same name, worked.
62. “Maria (Shut Up And Kiss Me)” from ‘The Great Divide’ (2002)
ShareComing off of his success with Santana’s “Smooth,” Matchbox Twenty’s Rob Thomas was a hotly sought-after songwriter. He wrote “Maria” for Willie, and sings backup on the song (as well as tending bar in the video). Yes, it sounds like it’s squarely aimed at early 2000s VH1, but it’s a great song and Willie delivers it perfectly.
61. “Vote ‘Em Out” (YouTube-only release, 2018)
ShareWillie released this single as he was endorsing Beto O’Rourke’s 2018 Senate campaign in Texas. While the endorsement upset some of his fans, the song doesn’t mention politicians or parties, and is really just a celebration of democracy: “If you don't like who's in there, vote 'em out/That's what Election Day is all about/The biggest gun we've got/Is called ‘the ballot box’/So if you don't like who's in there, vote 'em out!”
60. Willie Nelson featuring the Time Jumpers – “Heartaches By The Number” from ‘For The Good Times: A Tribute To Ray Price’ (2016)
ShareWillie pays tribute to his one-time mentor Ray Price, by doing songs that Price once covered. The Time Jumpers - a vintage-sounding country swing band featuring Vince Gill - gave the song a classic sound.
59. Willie Nelson and Asleep At The Wheel – “Hesitation Blues” from ‘Willie and the Wheel’ (2009)
ShareIf you want to party like it’s 1949, Asleep At The Wheel is the right band to call, and their 2009 collaborative album with Willie is a blast. “Hesitation Blues” kicked the party off.
58. “I Didn’t Come Here (And I Ain’t Leavin’)” from ‘It Always Will Be’ (2004)
Share‘It Will Always Be’ is one of Willie’s most underrated albums - there’s no theme and no stunt; it’s just Willie in peak form singing and playing great songs: some of which he wrote, and some, like this one, he didn’t. It’s a rowdy song about Willie making a mess of himself at a bar and then being asked to leave: “I didn't come here, and I ain't leavin'/I've been thrown into better places than this/I didn't come here, so I ain't leavin'/If you wanna pucker up I got just the place for you to kiss!” Maybe you can relate.
57. “I Never Cared For You” from ‘Teatro’ (1998)
Share“Teatro” is Spanish for theater, and this unique album saw Willie recording in an old movie theater; the sessions were produced by Daniel Lanois, who is well known for working with U2 and Bob Dylan. The album prominently featured Willie’s frequent collaborators Bobbie Nelson on piano and Mickey Raphael on harmonica, along with Emmylou Harris singing backing vocals. Willie first recorded “I Never Cared For You” in 1964, but this more seasoned version is an improvement on the original.
56. Willie Nelson and Ray Price – “Run That By Me One More Time” from ‘Run That By Me One More Time’ (2003)
ShareIn 1960, Willie Nelson moved from Texas to Nashville to make it in country music, and got a gig as Ray Price’s bassist (even though he wasn’t really a bass player). Soon, Nelson eclipsed Price as a country music star. Twenty years later, in 1980, the two recorded a duo album. 23 years after that, they did the follow-up, a very traditional-sounding country album. The excellent title track was the album’s highlight.
55. “What Was It You Wanted” from ‘Across The Borderline’ (1993)
ShareAnother of Willie’s most underrated albums. “What Was It You Wanted” was a Dylan song that was only four years old at the time, but Willie, assisted by producer Don Was, gave the song a swampy swagger.
54. “Who’ll Buy My Memories” from ‘The IRS Tapes: Who’ll Buy My Memories’ (1991)
ShareOriginally available only by mail order, the album featured just Willie and his guitar… no doubt to keep production costs down. As the title alludes to, the album was recorded to help pay Willie’s tax debt to the I.R.S. And while the song and album title is a bit on the nose, the song isn’t about W2 or W4 forms. It’s about the painful memories in the aftermath of a breakup: “A cottage small just built for two/A garden wall with violets blue/Who'll buy my memories of things that used to be?”
53. Carlos Santana featuring Willie Nelson – “They All Went To Mexico” from ‘Havana Moon’ (1983)
ShareIt sounds like a happy, almost Jimmy Buffett-esque song. All of the narrator’s friends, his girlfriend and even his dog went to Mexico, but in this song, “Mexico” seems to be a metaphor for the afterlife. “Where's my pal, where's my friend/All good things must have an end,” he sings. “Sad things and nothings/On and on they go/I guess he went to Mexico.”
52. Waylon Jennings and Willie Nelson – “Write Your Own Songs” from ‘WWII’ (1982)
ShareWritten by Willie who is sort of flipping the bird to the music industry here: “We write what we live and we live what we write, is that wrong?/If you think it is Mr. Music Executive/Why don't you write your own songs…We're making you rich and you're already lazy/So just lay on your a– and get richer or write your own songs!”
51. Willie Nelson with Waylon Jennings – “Take It To The Limit” from ‘Take It To The Limit’ (1983)
ShareFrom the duo’s third album together. This song is a cover of the Eagles, one of the leaders of the “country-rock” movement. The Eagles’ Randy Meisner was a much younger man when he recorded it, and the song definitely hit differently when the older Nelson sang “You know I've always been a dreamer /spent my life running ‘round/And it's so hard to change/Can't seem to settle down/But the dreams I've seen lately/Keep on turning out and burning out and turning out the same.”
50. Neil Young featuring Willie Nelson – “Are There Any More Real Cowboys?” from ‘Old Ways’ (1985)
ShareRock legend Neil Young went to Nashville in the ‘80s to make a legitimate country record, using local musicians and scoring guest appearances from Waylon Jennings, and on this song, his future Farm Aid co-founder Willie Nelson. The song poked fun at the “urban cowboy” trend of the time, and paid tribute to the farmers who work to feed the country. He was specific about the cowboys that he was paying tribute to: “Not the one that's snortin' cocaine/When the honky-tonk's all closed/But the one that prays for more rain/Heaven knows/That the good feed/Brings the money/And the money buys the clothes/Not the diamond sequins/Shining on TV.”
49. The Highwaymen – “Highwayman” from ‘Highwayman’ (1985)
ShareThis is a cover of a 1977 song by Jimmy Webb, but the Highwaymen’s version is the definitive one, and it became their signature song. The narrator is a soul who has lived many lives: a highwayman, a sailor, a construction worker on the Hoover Dam, and finally as a captain of a starship. In the song, Willie is the highwayman, Kris Kristofferson is the sailor, Waylon Jennings is the construction worker and Johnny Cash is the starship captain. It’s the supergroup’s finest moment.
48. “Cowboys Are Frequently, Secretly Fond Of Each Other” (single-only release, 2006)
ShareIt’s a cover of a 1981 song by a little-known musician named Ned Sublette. Someone gave Willie a tape of the song in the ‘80s, and two decades later, he decided to record it. As Willie said, “I thought it was the funniest goddamn song I'd ever heard.” The lyrics include, “Well, a cowboy may brag about things that he's done with his women/But the ones who brag loudest are the ones that are most likely queer/Cowboys are frequently secretly fond of each other/Say, what do you think all them saddles and boots was about?” Willie said, “I had [the tape] on the bus for 20 years, and people would come in and I'd play it. When ‘Brokeback Mountain’ come out, it just seemed like a good time to kick it out of the closet.” Willie told Time magazine, “Every now and then somebody might get a little offended. It's got bad language in it, so I just don't do it in my shows… But you know, people are listenin' to it, likin' it. Every now and then somebody don't like it, but that's okay. Similar to years ago, when the hippie thing come out and I started growin' my hair and puttin' the earring in, I got a little flak here and there.” And hey, these days plenty of country guys have long hair and earrings. Willie’s just always been a bit ahead of his time.
47. “Please Don’t Tell Me How The Story Ends” from ‘Willie Nelson Sings Kristofferson’ (1979)
ShareA lot of people have cited Kris Kristofferson as an amazing songwriter, but Willie recorded a whole album of his songs to make the point (and of course, they’d later be bandmates in the Highwaymen). And this song is a good example of why Kristofferson is so admired. He doesn’t give too many details, but it seems to be about the end of a sweet affair: “This could be our last goodnight together/We may never pass this way again/Just let me enjoy 'till it’s over /Or forever/Please don't tell me how the story ends.”
46. Willie Nelson and Leon Russell – “Heartbreak Hotel” from ‘One For The Road’ (1979)
ShareNot *all* songs about heartbreak have to be sad, of course! This rollicking version of the Elvis Presley classic from Willie and Leon Russell’s album pretty much says, “OK, I get so lonely, I could die… but until that happens, I’m gonna keep chasing women.”
45. “Blue Skies” from ‘Stardust’ (1978)
ShareBy the late ‘70s, Willie had established himself as one of the faces of the outlaw country movement, so his record label must have been surprised by his idea to record an album of popular music standards. Indeed, his label didn’t want him to do it, but Nelson was (and is) a true outlaw: he does what he wants. And in this case, he was right. “Blue Skies,” a cover of an Irving Berlin song from 1926, was his fourth #1 single on country radio.
44. “Loving Her Was Easier (Than Anything I’ll Ever Do Again)” from ‘Willie Nelson Sings Kristofferson’ (1979)
ShareAnother devastatingly sad song about a breakup, delivered perfectly by Willie.
43. “Till I Gain Control Again (live)” from ‘Willie And Family Live’ (1978)
ShareWritten by Rodney Crowell for Emmylou Harris, it was a #1 hit for Crystal Gayle in the ‘80s. But chart success aside, Nelson’s live cover is the best version. It’s a moving meditation on the need for solid friends/family/lovers. The lyrics ring so true it hurts: “Out on the road that lies before me now /There are some turns where I will spin /I only hope that you can hold me now/’Til I can gain control again.”
42. “Georgia On My Mind” from ‘Stardust’ (1978)
ShareA 1930 Hoagy Carmichael song, the most famous version was done by Ray Charles in 1960. Clearly, Willie has never been intimidated by recording iconic songs. And even if his version isn’t quite as great as Brother Ray’s, it’s still pretty incredible.
41. “If You’ve Got The Money, I’ve Got The Time” from ‘The Sound In Your Mind’ (1976)
ShareA 1950 hit for country legend Lefty Frizzell, it became Willie’s second country #1 single a quarter of a century later. And it remains one of Willie’s most joyous party jams.
40. “I’d Trade All Of My Tomorrows (For Just One Yesterday)” from ‘Country Favorites – Willie Nelson Style’ (1966)
ShareOne of Willie Nelson’s many strengths is that he picks great songs: sometimes, he writes them himself. Sometimes, they’re written for him. And sometimes he covers classics but puts his own spin on them. That’s the case with this weeper, written by Jenny Lou Carson.
39. “Last Thing I Needed, First Thing This Morning” from ‘Always On My Mind’ (1982)
ShareChris Stapleton recently recorded this one for his album, ‘From A Room: Vol. 1.’ The song was written for Willie by Gary P. Nunn and Donna Farar, and Willie took it to #2 on the country charts. In the song, the bills are “past due,” the narrator is going to be late to work, the house is falling apart. But, “The last thing I needed, first thing this morning, is to have you walk out on me.” Ouch.
38. “For The Good Times” from ‘Willie Nelson Sings Kristofferson’ (1979)
Share“Don’t look so sad,” Willie sings. “I know it’s over.” Whew, Kristofferson was good at breakup songs. There are a lot of great versions of this one, including Kristofferson’s own take, as well as soul legend Al Green’s incredible version. Willie’s version holds up to both of them.
37. “Darkness On The Face Of The Earth” from ‘And Then I Wrote’ (1962)
ShareFrom Willie’s debut album. Willie sounds like a kid, and the production here was way more “pop” than what you’d expect but the real shocker was the photo of him on the cover: he’s clean-shaven and he has short hair! Hey, it was 1962. But Willie was getting an early start with heartbreak jams: “I stumbled through the darkness, my footsteps were unsure/I lived within a world that had no sunshine/When you left me darling, my world came to an end/And there was darkness on the face of the earth.”
36. “Bloody Mary Morning” from ‘Phases and Stages’ (1974)
ShareWhile alcohol isn’t the substance that Willie is most often associated with, this song is based on his own experience, as he wrote in his autobiography: “‘Bloody Mary Morning’ was another boozy song about this boozy period of my life. Its origins might be found in those days on the road when I was living a double life...I was a lousy drunk, a foolish drunk, a fighting drunk, a drunk who did himself much damage. But I was caught up in the culture of drinking. That's what country singers did, right? That's what pickers did. That was the life.” There’s a wild version of the song by country punkers the Supersuckers featuring Willie on lead guitar.
35. “I’ll Love You Till The Day I Die” from ‘A Beautiful Time’ (2022)
Share*Sixty-five years* after his debut single (1957’s “No Place For Me”), Willie is still putting out new music. As you may have noticed on this list, he’s done so at a pretty prolific rate: he’s put out over 30 albums this millennium. And this song, written for him by Chris Stapleton and Rodney Crowell, ranks as one of his best.
34. “It’s Not Supposed To Be That Way” form ‘Phases and Stages’ (1974)
Share‘Phases and Stages’ is a painful album, even by Willie’s standards: it’s a concept album that documents a divorce. Side one tells the story from the woman’s side, and side two was from the man’s perspective. “It's not supposed to be that way/You're supposed to know I love you” speaks to the importance of communicating in your relationship.
33. “Sunday Mornin’ Comin’ Down” from ‘Willie Nelson Sings Kristofferson’ (1979)
ShareA number one hit on the country charts in 1970 for Johnny Cash, Willie first recorded it in 1971, but this version from 1979 is his best take on the classic. Funny enough, Waylon Jennings also recorded a version in 1971. The lyrics are also funny… in a tragic way: “Well, I woke up Sunday morning/With no way to hold my head that didn't hurt/And the beer I had for breakfast wasn't bad/So I had one more for dessert.”
32. “She’s Not For You” from ‘Shotgun Willie’ (1973)
ShareA sad tale about a guy warning another guy about a girl… and it seems he knows her deal from experience: “Pay no mind to her she only wants to play/She's not for you, she's not for you/And I'm the only one who would let her act this way.”
31. “Three Days” from ‘And Then I Wrote’ (1962)
Share30. “Sad Songs And Waltzes” from ‘Shotgun Willie’ (1973)
ShareIn which Willie tells a woman who broke his heart that he’s writing a song about her. But, he notes, she needn’t fear, for “sad songs and waltzes aren’t selling this year.”
29. “Mr. Record Man” from ‘And Then I Wrote’ (1962)
ShareIt’s a pretty “meta” song, about a sad lonely man listening to the radio… he hears a song that resonated with him. “The man that I heard singing sound so blue and all alone/As I listen to his lonely song, I wonder could it be?/Could there somewhere be another lonely man?/Like me.”
28. “City Of New Orleans” from ‘City Of New Orleans’ (1984)
ShareWritten and recorded by Steve Goodman in 1971, folk singer Arlo Guthrie recorded a version in ‘72, but Willie’s version in ‘84 is the definitive one, and it even topped the country charts that year.
27. “Shotgun Willie” from ‘Shotgun Willie’ (1973)
Share‘Shotgun Willie’ was Willie’s first album with Atlantic Records, and it was their first country release. Outside of the confines of a label who “knew” country music, Willie had a bit more freedom. Many feel that “outlaw country” started here. Willie sang “Well you can't make a record if you ain't got nothing to say/You can't play music if you don't know nothing to play.” Sixteen albums in, Willie still had a lot to say, but who could have predicted he’d still be knocking out records fifty years later!
26. “Blue Eyes Crying In The Rain” from ‘Red Headed Stranger’ (1975)
ShareOriginally recorded in 1947 by Roy Acuff. But you’d be forgiven for thinking that it’s a Willie original since it’s one of his signature songs. The song topped the country charts for Nelson and was even a #21 hit on the pop charts.
25. “Hello Walls” from ‘And Then I Wrote’ (1962)
ShareAnother early song that Willie wrote for Faron Young, who had a #1 hit with it. And yep, it’s another song for the dumped. After the narrator gets the bums rush, he has no one to talk to but the walls in his room. “Hello window/Well I see that you're still here/Aren't you lonely/Since our darlin' disappeared?/Well, look here, is that a teardrop/In the corner of your pane?/Now don't you try to tell me that it's rain.”
24. Toby Keith featuring Willie Nelson – “Beer For My Horses” from ‘Unleashed’ (2002)
ShareWillie’s setlists are mostly made up of vintage tracks, this is one of the few jams from this millennium that has made it to the stage. Toby Keith was a huge star at the time, and he brought Willie back onto the country airwaves thanks to this #1 hit.
23. “Picture In A Frame” from ‘It Always Will Be’ (2004)
ShareA gorgeous cover of an underrated Tom Waits song from his 1999 album ‘Mule Variations.’ Lots of love songs are written from the perspective of young folks. But this song, co-written by Waits and his wife and collaborator Kathleen Brennan, has lyrics that are simple but are about a long-term relationship. The tremor in Willie’s voice hints that maybe the object of the narrator’s love is no longer with him. “I come callin' in my Sunday best/Ever since I put your picture in a frame.”
22. “Angel Flying Too Close To The Ground (live)” from ‘Honeysuckle Rose – Music From the Original Soundtrack (1980)
ShareEven if you haven’t seen the film (which Nelson co-starred in), the song works, and it’s yet another heartbreaking line from Willie: “Fly on, fly on past the speed of sound/I'd rather see you up than see you down/So leave me if you need to, I will still remember/Angel flying too close to the ground.”
21. Willie Nelson featuring Paula Nelson – “Have You Ever Seen The Rain” from ‘To All The Girls…’ (2013)
ShareTalent runs in this family: Willie’s daughter Paula has a fantastic voice, and father and daughter’s voices work together perfectly on this downbeat version of the Creedence Clearwater Revival rocker.
20. Willie Nelson featuring Snoop Dogg, Kris Kristofferson and Jamey Johnson – “Roll Me Up” from “Heroes’ (2012)
ShareWillie, Snoop, Kris and Jamey sound like they’re having a blast here. Hmmm, what was going on in the studio that day? This is another rare new(ish) song that frequently makes Willie’s playlists. He has referred to it as a gospel song.
19. Willie Nelson featuring Bonnie Raitt – “Getting Over You” from ‘Across The Borderline’ (1993)
ShareAnother breakup song (as you may have gathered from the title). Here, Willie and Bonnie sing as if they’re a couple. Willie sings, “Why do I still write?/Why do I still call?/Why do I still think there's hope for us at all/These are the things I hate/But they're the things I do/To get over you.” Bonnie counters, “Sunsets make me cry/Old pictures make me grin/But I don't really care to see your face again/These are the things I say/But they're so hard to do/Like gettin' over you.” Their distinctive guitars have their own sad conversation, but all voices involved seem to have accepted that the relationship is over.
18. Willie Nelson featuring Paula Nelson – “Be That As It May” from ‘It Always Will Be’ (2004)
ShareWritten for Willie by his daughter Paula. Not only does she have a great voice, but she’s also a great writer: “It’s later than you think/Your whole life could change with or without me/A promise is a lie/With a prettier disguise/Like I’ll love you/For the rest of my life.”
17. Willie Nelson featuring Lukas Nelson – “Just Breathe” from ‘Heroes’ (2012)
ShareLukas Nelson suggested this classic Pearl Jam ballad to his dad, and their duet version of the song works perfectly, and it’s even made Willie’s setlists a handful of times.
16. Waylon Jennings and Willie Nelson – “Mammas Don’t Let Your Babies Grow Up To Be Cowboys” from ‘Waylon & Willie’ (1978)
ShareBy the late ‘70s, both Waylon and Willie were huge superstars, so putting them together on an album was a no-brainer. But this song, a cover of a singer named Ed Bruce, was the right tune with the right singers at the right time. It topped the country music charts for four weeks, while the album topped the country album charts for ten weeks.
15. “Stay All Night (Stay A Little Longer)” from ‘Shotgun Willie’ (1973)
ShareAnother instance where Willie took a classic from the fog of history and made it current; “Stay All Night” was a 1945 song by Bob Wills, but became a favorite at Willie’s shows.
14. “Time Of The Preacher” from ‘Red Headed Stranger’ (1975)
ShareThe opening track from Nelson’s concept album about a fugitive on the run from the law after he killed his wife and her lover. After she left him, “He cried like a baby/He screamed like a panther/In the middle of the night/And he saddled his pony/He went for a ride/It was the time of the preacher/In the year of '01/Now the preachin' is over/And the lesson's begun.” In 1986, a film was made based on the album, with Willie in the starring role. BTW: you can hear a wild version of the song from 1996, by Johnny Cash backed by Krist Novoselic of Nirvana, Kim Thayil of Soundgarden and Sean Kinney of Alice In Chains (it’s on YouTube).
13. “It Always Will Be” from ‘It Always Will Be’ (2004)
ShareThe title track from Willie’s 52nd album. He wrote this one himself, showing that he was still a top-notch songwriter, four decades into his career.
12. Merle Haggard and Willie Nelson – “Pancho and Lefty” from ‘Pancho & Lefty’ (1983)
ShareThe production on this one is very… well, it was obviously recorded in the ‘80s. But the song is so great, it’s easy to overlook the very “adult contemporary” sounding intro. The song is a cover of legendary songwriter Townes Van Zandt. Willie and Merle’s version topped the country charts, and even made it to #21 on the adult contemporary charts… so maybe they knew what they were doing with that production.
11. “Whiskey River” from ‘Shotgun Willie’ (1973)
ShareFirst written and recorded by Johnny Bush, it’s since become Willie’s song, and only Willie’s. It’s one of his signature jams. Fun fact: it was the first song ever performed on the live music TV show ‘Austin City Limits.’
10. “American Tune” from ‘Across The Borderline’ (1993)
ShareA cover of what might be Paul Simon’s finest solo song; Paul produced and played guitar on Willie’s version. There’s a lot on the narrator’s mind: “We come on the ship they call The Mayflower/We come on the ship that sailed the moon/We come in the age's most uncertain hours/And sing an American tune.” But then he realizes how late it is: “You can't be forever blessed/Still, tomorrow's going to be another working day/And I'm trying to get some rest.”
9. Julio Iglesias and Willie Nelson – “To All The Girls I’ve Loved Before” from ‘1100 Bel Air Place’ (1984)
ShareOk, here’s one with some serious adult contemporary production, and yeah, it really worked here, too. It topped the country charts, but also was a number 5 pop hit and helped Iglesias cross over to an English-speaking audience.
8. “Me and Paul” from ‘Yesterday’s Wine’ (1971)
Share‘Yesterday’s Wine’ was not a very successful album, and after the album’s release, Nelson retired from music… temporarily, obviously. But one classic from the album was “Me and Paul,” Willie’s tribute to his drummer and touring companion, Paul English. Willie wrote in his memoir that the song “described the road that my drummer and best friend, Paul English, and I had been riding together.” Sadly, English died in 2020.
7. “Making Believe” from ‘Country Favorites – Willie Nelson Style’ (1966)
ShareOriginally recorded by Kitty Wells in 1955, she had a #2 hit with the song. But it sounds like a Willie song; he’s pining over an ex-, lamenting, “Can't hold you close when you're not with me/You're somebody's love, you'll never be mine.”
6. Ray Charles and Willie Nelson – “Seven Spanish Angels” from ‘Friendship’ (1984)
ShareIn the ‘80s, fans might have forgotten that Ray Charles was once one of the most popular country singers in America, two decades earlier. This duet with Willie, from Ray’s ‘Friendship’ album, was a good reminder… and indeed, it topped the country charts.
5. “Night Life” from ‘Country Willie – His Own Songs’ (1965)
ShareAs the legend goes, Willie sold the song to his guitar teacher for $150, and the song was rejected by a record label for not being “country enough.” It was a preview of issues with the music industry that Nelson would have for decades to come. The guy who rejected it, of course, is but a footnote, while “Night Life” is a classic, and it has since been covered by Aretha Franklin, B.B. King, and Frank Sinatra.
4. “Crazy” from ‘And Then I Wrote’ (1962)
ShareThe song that put Willie on the map: he wrote it for Patsy Cline, who had a massive hit with it in 1961. It’s since gone on to become one of the most iconic songs in popular music history.
3. “Always On My Mind” from ‘Always On My Mind’ (1982)
ShareAnother classic that you might have thought Willie wrote. Nope: it was written by Wayne Carson, Johnny Christopher, and Mark James, and both Brenda Lee and Elvis Presley recorded it before Willie did. But with due respect to both of those legends, Willie owns this song. B.B. King told this writer that Willie’s version is his favorite song of all time.
2. “Funny How Time Slips Away” from ‘And Then I Wrote’ (1962)
ShareAnother of Willie’s early classics. He wrote it, but the original version was recorded by a singer named Billy Walker, who had a #23 hit with it. Apparently, Patsy Cline wanted it to be her follow-up to “I Fall To Pieces,” and she ended up “settling” for “Crazy” instead. Anyway, the version of “Funny How Times Slips Away” that we love is Willie’s. But Al Green, Tina Turner, the Supremes and Elvis Presley have all done good covers.
1. “On The Road Again (live)” from ‘Honeysuckle Rose – Music From The Original Soundtrack’ (1980)
ShareThe man has played over 2300 concerts in his lifetime; this song is his anthem. The life he loves really *is* making music with his friends. Nelson wrote the song for the film ‘Honeysuckle Rose,’ which he starred in. The movie is about an aging musician who never quite hits the big time; it’s also about his relationship with his family, who are part of his band … and they are on a seemingly endless tour. So the role wasn’t a stretch. Willie wrote the song at the request of one of the film’s producers, who asked for a song about life on the road. They were on a flight at the time, and according to legend, Nelson wrote the song on a barf bag.