Willie Nelson’s 90th birthday is Saturday, April 29. To celebrate this momentous occasion, the country music and cultural icon is throwing himself one heck of a birthday party at the Hollywood Bowl in Los Angeles. The two-day event boasts a stacked lineup featuring Neil Young, Chris Stapleton, Snoop Dogg, Kacey Musgraves, The Chicks, Margo Price, Orville Peck, and many more.

The first Willie Nelson album, …And Then I Wrote, came out in 1962. In the more than six decades since, he has released 98 studio albums, 14 live albums, and 51 compilations. As one of country music’s most prolific songwriters, Nelson has penned hits for Patsy Cline, Roy Orbison, and Waylon Jennings, to name a few. 

The cultural legacy attached to Willie Nelson (it would feel most natural to refer to him as just “Willie”) goes well beyond his storied music career. Over the years, he has used his influence to advocate for important causes like LGBTQ rights, animal welfare, and immigration. In 1985, he started Farm Aid with Neil Young and John Mellencamp to bring awareness to the importance and struggles of family farms across America. The annual benefit concert is hosted by a different heartland city each year and has boasted an impressive lineup of artists since day one. 

Of course, no conversation about Willie Nelson’s cultural impact would be complete without discussing his love of weed. He’s a central pillar of the marijuana legalization movement that has influenced nearly half the U.S. to put recreational cannabis laws on the books. And if there was ever any doubt about his dedication to the devil’s lettuce, well…

In addition to his music career, Willie Nelson has left his mark on Hollywood. Since his big screen debut in 1979’s The Electric Horsemen, he’s racked up nearly 60 acting credits over the years, including starring roles in Honeysuckle Rose, Red Headed Stranger, Barbarosa, and Songwriter, as well as supporting roles in Half Baked, Wag the Dog, and The Dukes of Hazzard, among many others. He’s also appeared in several popular TV shows like Miami Vice, Monk, King of the Hill, and The Simpsons. 

For those of us not fortunate enough to make it to his birthday party, this weekend is a perfect opportunity to take a deep dive into the nonagenarian’s expansive catalog. To make that dive more efficient, here are 90 career-defining Willie Nelson songs, from his biggest hits to more-obscure recordings.

Early Songwriting Gems

“The Storm Has Just Begun”

Willie’s first song that he wrote when he was only 12. It eventually ended up as a b-side of the “Man With The Blues” single and later appeared on Texas Willie.
Album: Willie Nelson - Texas Willie (2021)

“Crazy”
“Darkness on the Face of the Earth”
“Funny How Time Slips Away”
“Hello Walls”

Willie Nelson’s first album, …And Then I Wrote, yielded songs that still resonate today. Among them, “Crazy,” which was written by Willie, and made massively famous by Patsy Cline. The Willie standard “Funny How Time Slips Away” has been covered countless times, including by Linda Ronstadt and Homer Simpson on The Simpsons’ The Yellow Album.
Album: Willie Nelson - …And Then I Wrote (1962)

“I Never Cared For You” with Emmylou Harris

Originally written in 1964 during Willie’s stint at Monument Records, this song has been reworked and released several different times over the years. The Teatro version features hauntingly beautiful background vocals from frequent collaborator Emmylou Harris.
Album: Willie Nelson - Teatro (1998)

Outlaw Classics & Smash Hits

“On the Road Again”

Arguably Willie’s most well-known song, “On the Road Again,” first appeared on the Honeysuckle Rose soundtrack, but he’s cut dozens of versions of it over the years. The track earned Willie a Grammy for Best Country Song, making it possibly the only Grammy-winning song to be written on an airplane barf bag.
Album: Willie Nelson & Family - Honeysuckle Rose Soundtrack (1980)

“Always On My Mind”
“Bridge Over Troubled Water” (Simon & Garfunkel)

Willie performed the Simon & Garfunkel classic at the opening ceremony for the 2002 Winter Olympics in Salt Lake City, Utah.
Album: Willie Nelson - Always On My Mind (1982)

“City of New Orleans”

Album: Willie Nelson - City of New Orleans (1984)

“Blue Eyes Crying In the Rain”
“Red Headed Stranger”

Album: Willie Nelson - Red Headed Stranger (1975)

“Georgia on My Mind (Live)” with Ray Charles

This version was captured live on The Willie Nelson Special in 1985.
Album: Willie Nelson - The Made in the USA Collection (2018)

“Sad Songs and Waltzes”
“Shotgun Willie”
“Whiskey River”

Album: Willie Nelson - Shotgun Willie (1973)

“Highwayman” (Jimmy Webb) with Johnny Cash, Waylon Jennings, and Kris Kristofferson

Album: The Highwaymen - Highwayman (1985)

“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” with Waylon Jennings

Album: Waylon Jennings / Willie Nelson - Waylon & Willie (1978)

“Luckenbach, Texas (Back to the Basics of Love)” with Waylon Jennings

Album: Waylon Jennings - Ol’ Waylon (1977)

“Who’ll Buy My Memories”
“Pretend I Never Happened”

Willie recorded The IRS Tapes: Who’ll Buy My Memories with only his trusty guitar, Trigger, by his side after the IRS seized all of his assets due to his $32 million tax debt. All proceeds from the album went directly to the IRS. The album’s title track features one of Willie’s most emotional vocal performances of his entire career. Initially written by Willie and recorded by Waylon Jennings, Willie later included “Pretend I Never Happened” on both Phases and Stages and The IRS Tapes.
Album: Willie Nelson - The IRS Tapes: Who’ll Buy My Memories (1992) 

“You Left Me A Long, Long Time Ago”
“Mountain Dew” (Bascom Lamar Lunsford & Scotty Wiseman)

Album: Willie Nelson - The Willie Way (1972)

“September Song”
“Stardust”

Album: Willie Nelson - Stardust (1978)

“December Day”
“Family Bible”
“Yesterday’s Wine”

Album: Willie Nelson - Yesterday’s Wine (1971)

“No Place But Texas”

Album: Willie Nelson - The Promiseland (1986)

“The Great Divide”

This great Western ballad has an almost flamenco-esque guitar.
Album: Willie Nelson - The Great Divide (2002)

“Forgiving You Was Easy”

Album: Willie Nelson - Me and Paul (1985)

“Pretty Paper”

This holiday classic was written by Willie, and made famous by Roy Orbison.
Album: Willie Nelson - Pretty Paper (1979)

“Bloody Mary Morning”

Album: Willie Nelson - Phases And Stages (1974)

“Little Old Fashioned Karma”

Album: Willie Nelson - Tougher Than Leather (1983)

“I’d Have To Be Crazy”

Album: Willie Nelson - The Sound in Your Mind (1976)

Top Collaborations

Willie has collaborated with just about everyone from outlaw country contemporaries like Waylon Jennings, Merle Haggard, and Johnny Cash, to R&B superstars like Ray Charles and Brian McKnight, and rapper Snoop Dogg, not to mention rock and roll icons Dr. Teeth and the Electric Mayhem. Additionally, in 1995, he formed the outlaw country supergroup the Highwaymen along with Johnny Cash, Waylon Jennings, and Kris Kristofferson. 

“Pancho & Lefty” with Merle Haggard

Album: Willie Nelson / Merle Haggard - Pancho & Lefty (1983)

“Angel Flying Too Close to the Ground” with Mark McGrath

Originally written for the Honeysuckle Rose soundtrack, Willie rerecorded “Angel Flying Too Close to the Ground” as a duet with Mark McGrath from Sugar Ray for the King of the Hill soundtrack. While that sentence may read like a Mad Lib, this version of is truly phenomenal. The ad for Dale’s Dead Bug at the end is just the icing on the cake.
Album: Various Artists - King of the Hill Soundtrack (1999)

“Don’t Give Up” (Peter Gabriel & Kate Bush) with Sinéad O’Connor

Album: Willie Nelson - Across the Borderline (1993)

“Under Pressure” (David Bowie & Queen) with Karen O

Album: Karen O & Willie Nelson - Under Pressure

“Against the Wind” (Bob Seger)
“The Last Cowboy Song”
“Big River” (Johnny Cash) all with Johnny Cash, Waylon Jennings, and Kris Kristofferson

No Willie playlist curated by a Minnesota radio station is complete without this version of “Big River,” Cash’s love letter to the Mississippi River. It even includes a St. Paul shoutout.
Album: The Highwaymen - Highwayman (1985)

“To All the Girls I’ve Loved Before” with Julio Iglesias

AUTHOR’S NOTE: This song was my first exposure to Willie Nelson. Well, sort of. My parents had a Best of Johnny Carson VHS box set when I was growing up. This rendition of “To All the Girls I’ve Loved Before” was one of the featured clips, and it wasn’t until years later that I realized that it wasn’t actually Willie Nelson.
Album: Julio Iglesias - 1100 Bel Air Place (1984)

“Seven Spanish Angels” with Ray Charles

Album: Ray Charles - Friendship (1984)

“Are There Any More Real Cowboys?” with Neil Young

Willie and Neil Young (along with John Mellencamp) founded the annual benefit concert Farm Aid in 1985 to help American farmers. They regularly perform together at Farm Aid concerts, including in 1993, when they delivered a particularly impassioned version of Young’s “Last of His Kind.”
Album: Neil Young - Old Ways (1985)

“Roll Me Up and Smoke Me When I Die” with Snoop Dogg, Kris Kristofferson, and Jamey Johnson

Album: Willie Nelson - Heroes (2012) 

“Angel Eyes” with Emmylou Harris

When two of the most distinct voices in country music team up, the results are bound to be pure magic. And, of course, they are.
Album: Willie Nelson & Family - Honeysuckle Rose Soundtrack (1980)

“(Ghost) Riders In The Sky” with Johnny Cash

In this live version, Willie and Johnny’s voices create an almost unbelievable harmony. During the banter at the end, Willie talks about covering a Johnny Cash song for his reggae album.
Album: Johnny Cash Willie Nelson - VH1 Storytellers (1998)

“Everything’s Beautiful (In It’s Own Way)” with Dolly Parton

Album: Kris Kristofferson, Willie Nelson, Dolly Parton & Brenda Lee - The Winning Hand (1982)

“Write Your Own Songs” with Waylon Jennings

Album: Waylon Jennings / Willie Nelson - WWII (1982)

“Beer For My Horses” with Toby Keith

Album: Toby Keith - Unleashed (2002)

“I Gotta Get Drunk” with George Jones

Album: George Jones - My Very Special Guests (1979)

“Walkin’” with Norah Jones

Album: Willie Nelson - To All The Girls… (2013)

“Learning to Lose” with Margo Price 

Album: Margo Price - All American Made (2017)

“Are You Sure” with Kacey Musgraves

Album: Kacey Musgraves - Pageant Material (2015)

“Will You Still Love Me Tomorrow?” with Carole King

Album: Willie Nelson & Friends - Outlaws and Angels (2004)

“We Are The World” with USA for Africa

This charity single was written by Michael Jackson and Lionel Richie, and performed by supergroup U.S.A. For Africa, which featured Willie, Stevie Wonder, Dionne Warwick, Bob Dylan, Bruce Springsteen, Ray Charles, Tina Turner,  and many more.
Album: Various Artists - U.S.A. For Africa: We Are The World (1985)

Best Covers

Perhaps one of Willie’s biggest strengths as an artist is his ability to cover beloved songs and make them entirely his own. Throughout his lengthy career, he’s covered hundreds, if not thousands, of songs across nearly every genre. The list of artists who’ve received the Willie treatment includes Coldplay, Pearl Jam, Cyndi Lauper, Bob Dylan, Elton John, and many others. He even covered Kermit the Frog!

“The Scientist” (Coldplay)

Willie’s heart-wrenching Coldplay cover was initially released as an Apple iTunes single as part of a Chipotle campaign. It was later included as a bonus track on Heroes.
Album: Willie Nelson - Heroes (2012)

“Cowboys Are Frequently Secretly Fond of Each Other” (Ned Sublette)

This cover was released on Valentine’s Day 2006 in the wake of the success of Brokeback Mountain.
Album: Willie Nelson - Lost Highway (2009)

“Over the Rainbow” (The Wizard of Oz)

An absolutely gutting cover of the song Judy Garland made famous. 
Album: Willie Nelson - Somewhere over the Rainbow (1981)

“The Rainbow Connection” (The Muppet Movie)

Try and listen to this cover of Kermit the Frog’s show-stopper without tearing up. You can’t.
Album: Willie Nelson - Rainbow Connection (2001)

“Just Breathe” (Pearl Jam) with Lukas Nelson 

This tragically beautiful Pearl Jam cover features Willie’s son Lukas.
Album: Willie Nelson - Heroes (2012)

“Crazy Arms” (Ray Price)
“Both Sides Now” (Joni Mitchell)

Album: Willie Nelson - Both Sides Now (1970)

“Don’t Think Twice, It’s Alright” (Bob Dylan) with Merle Haggard 

This Bob Dylan cover comes from Haggard and Willie’s sixth and final collaboration.
Album: Willie Nelson / Merle Haggard - Django and Jimmie (2015)

“It’s Hard to Be Humble” (Mac Davis) with Lukas Nelson and Micah Nelson 

Album: Willie Nelson - Ride Me Back Home (2019)

“Ou Es-Tu, Mon Amour? (Where Are You, My Love?)” (Django Reinhardt)

Album: Willie Nelson - Teatro (1998)

“What a Wonderful World” (Louis Armstrong)

Album: Willie Nelson - What A Wonderful World (1988)

“Warmth of the Sun” (The Beach Boys)

Album: The Beach Boys - Stars and Stripes: Vol. 1 (1996)

“Bird on a Wire” (Leonard Cohen)

Album: Various Artists - Tower of Song: The Songs of Leonard Cohen (1995)

“Summertime” (George Gershwin)

Willie is a lifelong Gershwin fan, so it’s no surprise he released this album. While the whole album is solid, “Summertime” is the standout track. Willie’s love of Gershwin made him a natural choice as a collaborator on Amanda Shires’ cover of “Summertime,” just released on April 26. The track is the first single off Shires’ upcoming album with Willie’s son, Bobbie Nelson.
Album: Willie Nelson - Summertime: Willie Nelson Sings Gershwin (2016)

“My Way” (Frank Sinatra)

Album: Willie Nelson - My Way (2018)

“Heart of Gold” (Neil Young)

Album: Willie Nelson - Partners (1986)

“Take It to the Limit” (Eagles)

Album: Willie Nelson with Waylon Jennings - Take It to the Limit (1983)

“Border Song” (Elton John)

Album: Various Artists - Restoration: Reimagining the Songs of Elton John and Bernie Taupin (2018)

“Unchained Melody” (The Righteous Brothers)

Album: Willie Nelson - Stardust (1978)

“Hallelujah” (Leonard Cohen)

Album: Willie Nelson - Songbird (2006)

“I’m So Lonesome I Could Cry” (Hank Williams) with Lukas Nelson and Micah Nelson 

Willie’s cover of Williams’ 1949 country standard features Willie’s sons, Lukas and Micah. The trio of Nelson voices meld to create a beautiful rendition that would surely make Hank proud.

Album: Willie and the Boys - Willie’s Stash Vol. 2 (2017)

Wild Cards

While Willie’s roots obviously lie in country music, he’s never turned down an opportunity to get outside his comfort zone and experiment with different genres. Throughout his career, he’s dabbled in jazz, blues, and polka. He even released an entire reggae album with 2005’s Countryman.

“Waltz Across Texas” (Ernest Tubb) with Jimmy Sturr 

Album: Jimmy Sturr - Gone Polka (2001)

“I’m A Worried Man” (Johnny Cash) with Toots Hibbert
“The Harder They Come” (Jimmy Cliff)

Album: Willie Nelson - Countryman (2005)

“Time After Time” (Cyndi Lauper)
“Don’t Fade Away” with Brian McKnight

Album: Willie Nelson - The Great Divide (2002)

“Bright Lights, Big City” with Wynton Marsalis

Album: Willie Nelson / Wynton Marsalis - Two Men With The Blues (2008)

“Night Life” with B.B. King

Album: B.B. King - Deuces Wild (1997)

“Frosty the Snowman”

Album: Willie Nelson - Pretty Paper (1979)

The Later Years

“Cruel World”

Album: Various Artists - The Music of Red Dead Redemption II (2019)

“He Was a Friend of Mine” (Bob Dylan)

Album: Various Artists - Brokeback Mountain Original Motion Picture Soundtrack (2005)

“Vote ‘Em Out”

Willie released this stand-alone single in the midst of the 2018 Senate election in Texas.

“I’ll Love You Till The Day I Die” (Chris Stapleton / Rodney Crowell)
“I Don’t Go To Funerals”

The chorus features the brilliant line, “I don’t go to funerals / And I won’t be at mine.”

Album: Willie Nelson - A Beautiful Time (2022)

This is a collection of 90 treasures from Willie’s catalog, but there are many more worth celebrating. Leave your favorites in the comments. Happy 90th, Willie!

Willie Nelson & Family lead the Outlaw Music Festival on June 23 at Somerset Amphitheater in Somerset, Wisc. Find more info here.