Country singer/songwriter Willie Nelson poses for a portrait with an electric guitar in circa 1967. / Willie Nelson performs in concert at Luck Ranch on March 26, 2022 in Spicewood, Texas.
Photo by Michael Ochs Archives/Getty Images/ Gary Miller/Getty Images for Shock Ink

Willie Nelson Through the Years: Look Back at 9 Decades in Photos

Born on April 29, 1933, in Abbott, Texas, singer and activist Willie Nelson is one of the most recognizable faces in country music. The living legend, whose songs include "On the Road Again" and "To All the Girls I've Loved Before," has appeared in over 30 movies and is an advocate for biofuels and the legalization of marijuana. Nelson has been honored with 13 Grammys and has sold more than 40 million albums in the United States since starting his career in the 1950s.

He's an icon with an undeniable influence on the music industry in general. Not to mention he's collaborated with some of the other great names in country music from fellow Highwaymen Johnny Cash and Kris Kristofferson to current stars Kacey Musgraves and his own son, Lukas Nelson.

Keep reading to take a look back at Nelson through the decades, from his high school days to maintaining his status as a superstar well into his 80s.

1949: Nelson is a Star Athlete in High School

Nelson was gifted his first guitar at age six, began singing in the church choir, wrote his first song at age seven, and played guitar for the band Bohemian Polka at age nine. Although his love of music started at an early age, Nelson still found time to excel at sports in high school, where he played baseball, basketball and football. After high school, Nelson enlisted in the U.S. Air Force for nine months before being discharged due to back issues.

1955: Nelson Makes His First Two Recordings

Country singer/songwriter Willie Nelson (second from left) performs onstage with a band in circa 1955 in Texas.

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Nelson made his first two recordings, "The Storm Has Just Begun" and "When I've Sung My Last Hillbilly Song," in 1955 and sent them to a local radio station, who rejected them. But he didn't give up that easily. Undeterred, Nelson kept playing with local bands and made his first record, "No Place for Me," in 1956. He moved to Nashville in 1960 and tried to find a record label that would sign him.

1965: Nelson Joins the Grand Ole Opry

Country singer/songwriter Willie Nelson poses for a portrait holding an electric guitar in circa 1965.

Photo by Michael Ochs Archives/Getty Images

In 1964, Nelson signed a recording contract with RCA Victor, which released Country Willie — His Own Songs in 1965. That same year, Nelson joined the Grand Ole Opry, where he met and became friends with Waylon Jennings after seeing him perform. Although Nelson didn't have any major hits in the 1960s, several of his songs cracked the top 25 on the country charts, including "One in a Row," "The Party's Over" and "Bring Me Sunshine."

1975: Nelson Scores His First Number-One Country Hit

Willie Nelson, U.S. country music singer-songwriter, during a concert performance, circa 1975.

David Redfern/Redferns/Getty Images

It's hard to believe Nelson thought about retiring from country music in the early 1970s, but that is exactly what he did before moving to Austin, Texas and being rejuvenated by the city's outlaw country scene. After signing a contract with Columbia giving him complete creative control in 1975, Nelson released the concept album Red Headed Stranger, which contains the No. 1 country hit "Blue Eyes Crying in the Rain." Other 1970s hits include "Mammas Don't Let Your Babies Grow Up to Be Cowboys," "Good-Hearted Woman," "If You've Got the Money I've Got the Time," "Uncloudy Day" and "Remember Me."

1985: Nelson Helps Set Up Farm Aid

Willie Nelson Farm Aid 1985

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Nelson's 1982 cover of "Always on My Mind" topped the country charts, peaked at number five on the Billboard Hot 100, and won Nelson three Grammys. Now a bona fide country superstar, Nelson used his celebrity clout to help set up Farm Aid in 1985 along with Neil Young and John Mellencamp. This annual benefit concert for American farmers is still held today, with Nelson performing as recently as Farm Aid 2021.

1993: Nelson Clears Debts with the IRS

American country musician Willie Nelson performs, with the Highwaymen, at Central Park SummerStage, New York, New York, May 23, 1993.

Photo by Jack Vartoogian/Getty Images

One of the reasons Nelson looks so happy in this concert photo from 1993 is that it is the same year that he cleared all his debts with the IRS. In 1990, the IRS said that Nelson owed a whopping $32 million and seized most of his assets. Nelson released the 1992 album The IRS Tapes: Who'll Buy My Memories? with all proceeds going to the IRS to pay off his debt, which was negotiated down by his lawyer.

2003: Nelson's Duet with Toby Keith Is a Huge Hit

Wille Nelson and Toby Keith


In 2003, Nelson scored a big hit with Toby Keith titled "Beer for My Horses." The song spent six consecutive weeks sitting atop the Billboard Hot Country Songs chart. Two years later, Nelson headlined the 2005 Tsunami Relief Austin to Asia benefit concert, which raised $75,000 for the victims of the 2004 Indian Ocean earthquake.

2013: Nelson Releases a Hit Album of Duets with Female Singers

Keith Urban's Fourth Annual We're All For The Hall Benefit Concert

Frederick Breedon IV/Getty Images for the Country Music Hall of Fame and Museum

Nelson's 2013 album, To All the Girls..., features duets with female singers such as Dolly Parton, Loretta Lynn, Rosanne Cash, Sheryl Crow, Mavis Staples, Norah Jones, Emmylou Harris, Carrie Underwood and Miranda Lambert. The album became Nelson's highest position on the Billboard Hot Country Albums chart since 1989. He followed it up with 2014's Band of Brothers, which topped the Billboard Hot Country Albums chart. He closed the decade with 2019's Ride Me Back Home, the title track of which won Nelson a Grammy for Best Country Solo Performance.

2022: Nelson Releases His 72nd Solo Studio Album

Willie Nelson 2022

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During the COVID-19 lockdowns, Nelson live-streamed a series of benefit concerts to help people financially devastated by the pandemic. In celebration of his 89th birthday on April 29, 2022, Nelson released his 72nd (!!) solo studio album, A Beautiful Time, which includes original songs and covers of the Beatles and Leonard Cohen. We can honestly say that this American icon, singer, activist, actor, husband and father of seven has always been on our mind.

READ MORE: 'Whiskey River' The Story Behind Willie Nelson's Concert Staple