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The magical Willie Nelson playlist
Willie Nelson isn’t just a country legend, but he’s a whole mood. His songs somehow feel like they’ve always been part of your life.
Whether you’re rolling down backroads or sitting in silence, his music can hit the soul just right. This playlist highlights the must-hear tracks that made him an icon and proves why Willie still plays on repeat for generations.
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Blue Eyes Crying in the Rain (1975)
“Blue Eyes Crying in the Rain” is a country song by Fred Rose. It was first recorded by Elton Britt in 1946 and Roy Acuff in 1947. Willie Nelson recorded it for his 1975 album Red-Headed Stranger.
The single came out in July 1975 and hit number one on the Billboard Country Charts on October 4, 1975. The song is about lost love and memories. Nelson produced it himself. It runs 2 minutes and 18 seconds, with “Bandera” as the B-side.
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On the Road Again (1980)
On the Road Again” is a famous song written and recorded by Willie Nelson in 1980. He wrote it during a flight for the movie Honeysuckle Rose, where he played the lead role as an aging musician chasing fame.
The song became the film’s theme and celebrates the fun of life on the road, playing music and traveling with friends.
It hit number one on the country charts and reached number 20 on the Billboard Hot 100. It won a Grammy for Best Country Song in 1981 and became one of Nelson’s most iconic hits.
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Always on My Mind (1982)
Willie Nelson’s Always on My Mind album came in February 1982 and became a huge success. It hit number one on the Billboard Top Country Albums chart for 22 weeks and stayed on it for 253 weeks.
It reached number two on the Billboard 200 and stayed there for 99 weeks. The album features country, pop, and rock and roll and includes hits like “Always on My Mind,” “Let It Be Me,” and “Last Thing I Needed First Thing This Morning.”
It won three Grammys in 1983 and two CMA awards in 1982. It was certified platinum in 1991.
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Crazy (1961)
“Crazy” is a classic country song written by Willie Nelson and made famous by Patsy Cline. It was released in October 1961 and quickly became her signature song. Cline’s version hit number two on the Billboard country chart and nine on the Hot 100.
The song is now seen as a country music standard and has been covered by many artists. It was honored by being added to the Grammy Hall of Fame and the National Recording Registry. “Crazy” also holds the title of the most-played song ever on U.S. jukeboxes.
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Whiskey River (1973)
“Whiskey River” is a well-known song often linked to Willie Nelson, but it was actually written by Johnny Bush and Paul Stroud. Bush recorded and released it in 1972, and Nelson included his version on the 1973 album Shotgun Willie.
Even though Nelson didn’t write it, the song became one of his signature tunes and the usual opener for his concerts since around 1974. He released a live version as a single in 1978 on Willie and Family Live.
Mammas Don’t Let Your Babies Grow Up to Be Cowboys (1978)
In 1978, Willie Nelson and Waylon Jennings released a duet version of “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” on their album Waylon & Willie. The song was first written and recorded by Ed Bruce in 1976.
Nelson and Jennings’ version became a big hit, reaching number one on the Hot Country Singles chart and 42 on the Billboard Hot 100.
Their performance was so well-loved that it won a Grammy Award in 1979 for Best Country Performance by a Duo or Group with Vocal.
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Angel Flying Too Close to the Ground (1981)
“Angel Flying Too Close to the Ground” is a song written and performed by Willie Nelson. It first appeared on the Honeysuckle Rose movie soundtrack in 1980 and was released as a single in January 1981.
The song hit number one on the Billboard country chart in March 1981, becoming Nelson’s seventh solo number one. Some believe the song is about a tough relationship or a hard time in Nelson’s life, possibly involving his ex-wife.
Nelson said he waited for the right time to release it. He also performed it on The Muppets with the Electric Mayhem Band. Claude Gray recorded a popular version, too.
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Hello Walls (1961)
“Hello Walls” is a country song written by Willie Nelson and first recorded by Faron Young. It was released on February 27, 1961, and became a big hit.
The song hit number one on the Billboard country chart for nine weeks and peaked at number 12 on the pop chart. It stayed on the country chart for 23 weeks total. The lyrics is about the story of a lonely man talking to the walls in his room.
This song was a significant success for Faron Young and helped introduce Willie Nelson to a national audience as a talented songwriter.
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Good Hearted Woman (1972)
Willie Nelson co-wrote “Good Hearted Woman” with Waylon Jennings. Jennings first recorded it as the title track of his 1972 album, which helped shape the outlaw country image for both artists.
Even though Nelson only added a few lines, he got half the royalties. In 1976, they released a duet version on the album Wanted! The Outlaws, which made the song even more popular.
That album became a huge success and was the first platinum album in country music history. The song remains one of the most iconic outlaw country hits ever recorded.
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To All the Girls I’ve Loved Before (1984)
“To All the Girls I’ve Loved Before” was written by Albert Hammond and Hal David and first recorded by Hammond in 1975. The most famous version came in 1984 when Julio Iglesias and Willie Nelson recorded it for Iglesias’s album 1100 Bel Air Place.
Their duet became a big hit, reaching number one on the country chart and five on the Billboard Hot 100. It helped Iglesias break into the English-language market.
The song was released as a 7″ vinyl single by CBS, with “I Don’t Want to Wake You” as the B-side. It’s a smooth country pop song that runs 3 minutes and 30 seconds.
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Night Life (1960)
Willie Nelson wrote “Night Life” in 1960 while driving between his home in Pasadena and his job at the Esquire Ballroom in Houston. Because of money problems, he sold the song to Paul Buskirk for $150.
It was first released as “Nite Life” by Paul Buskirk and the Little Men featuring Hugh Nelson. Nelson’s label, D Records, rejected it for not being country enough. It was later re-released in 1963 under Nelson’s name by Bellaire Records.
The song was recorded at Gold Star Studios in Houston, produced by Bill Quinn, and had “Rainy Day Blues” as the B-side. It runs 2:35 and is considered a country classic.
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Georgia on My Mind (1978)
Willie Nelson released his version of “Georgia on My Mind” in 1978 as part of his Stardust album, which featured classic standards.
The song, written by Hoagy Carmichael and Stuart Gorrell in 1930, became Nelson’s first number-one hit on the US Hot Country Songs chart and reached number 84 on the Billboard Hot 100.
It topped the Canadian RPM Country Tracks chart, too. The song follows a 32-bar AABA structure. Nelson’s version won the Grammy for Best Male Country Vocal Performance in 1979.
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Funny How Time Slips Away (1961)
“Funny How Time Slips Away” is a song written by Willie Nelson in 1961, during the same week he wrote “Crazy” and “Night Life.” It was first recorded by country singer Billy Walker and released as a single by Columbia Records in June 1961.
Walker’s version reached number 23 on the Billboard Hot Country Singles chart and later appeared on his 1963 Greatest Hits album.
The song is about the story of two former lovers catching up after time apart. It played a significant role in helping establish Nelson’s name as a top songwriter in country music.
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Roll Me Up and Smoke Me When I Die (2012)
“Roll Me Up and Smoke Me When I Die” is a song by Willie Nelson, released on April 20, 2012, as a single and included on his album Heroes. The song was first going to be the album title, but they changed it to avoid hurting sales in certain stores.
It features guest vocals from Snoop Dogg, Kris Kristofferson, and Jamey Johnson. Willie performed it the same day during his statue in Austin.
The song has a bold, funny tone that shows Nelson’s laid-back views on death and cannabis. A green vinyl version with a solo cut came out for Record Store Day.
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The Wall (2014)
“The Wall” is a song by Willie Nelson, released as a single on May 6, 2014, and later included on his album Band of Brothers. Willie co-wrote it with Buddy Cannon.
The music video, which shows parts of his career, premiered on Rolling Stone the same day.
An acoustic version came out on Willie’s website in June 2014. The album, mostly made up of Nelson’s songs, was praised by critics, and “The Wall” stood out for his honest vocals, just as Willie Nelson announced his 76th solo album.
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Last Updated: September 24, 2025
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