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Willie Nelson Young: Must-See Photos of the Country Icon Before the Braids

It's hard to believe he started way back in the '50s — and he's still going strong!

Willie Nelson is a true living legend of country music. He’s been in the industry for over 60 years, and at 90, he’s still going strong and is beloved by many generations of fans. Even those who are not familiar with Nelson’s body of work can probably picture him — his long braids, bushy beard and easygoing smile have been iconic for decades.

Nelson may be known as one of the founding fathers of outlaw country, thanks to his rebellious spirit and embrace of the counterculture, but his career started long before that musical movement took off in the ’70s. In honor of his new album, The Border, coming out in May, here’s a look back at Willie Nelson young — before he started sporting his famous braids!

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Willie Nelson young: ’50s beginnings

Born in Texas in 1933, Nelson wrote his first original song when he was just 7 years old and never stopped, becoming a professional musician in the late ’50s, when he was in his 20s. In his recent book, Energy Follows Thought: The Stories Behind My Songs, he recalled those early days, writing, “The moment I found a way to make money making music, I was gone.”

Nelson didn’t find immediate success, but he was determined to keep writing songs no matter what. As he described in the book, “I was down and out. Didn’t have a clue of what a song might be worth. All I knew is that I had to write them.” During this time, he began selling songs to other artists.

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Willie Nelson young with various other musicians in 1955
Willie Nelson young, age 22, (second from left) onstage with a band in 1955Getty

In 1956, Nelson recorded his first single, “No Place for Me,” but it failed to find an audience. He spent the ’50s working as a DJ and taking on odd jobs, including selling vacuums and encyclopedias as a door-to-door salesman.

1957 brought a turning point in young Willie Nelson’s career, as he wrote the song “Family Bible,” which became his first hit when it was recorded by Claude Gray in 1960. Looking back on the pivotal song, Nelson wrote, “A song about faith gave me the faith to move to Nashville, where, in the ’60s, I found my footing as a songwriter” — and from there his profile continued to rise.

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Willie Nelson young: ’60s breakthrough

Nelson started the ’60s off strong. He wrote a number of songs that became hits for other artists, including “Crazy” (performed by Patsy Cline in 1961), “Funny How Time Slips Away” (performed by Billy Walker in 1961) and “Pretty Paper” (performed by Roy Orbison in 1963).

Fred Foster, president of Monument Records, poses with his newest signees, Fred Carter (left) and Willie Nelson in circa 1960
Left to right: Musician Fred Carter, Monument Records President Fred Foster and Willie Nelson, age 27, in 1960Getty

“Crazy,” which became Cline’s signature song and a country music standard, gave Nelson his biggest early success. As he wrote, “Crazy is as crazy does, and this particular ‘Crazy’ convinced me, at a time when I wasn’t a hundred percent sure of my writing talent, that I’d be crazy to stop writing.”

In 1962, Nelson released his debut album, …And Then I Wrote. The single “Touch Me” made it to number 7 on Billboard‘s country chart, and the album kicked off a wildly prolific career. Since then he’s released 73 solo studio albums, and if you count collaborative albums, live albums and compilation albums his discography goes up to over 100 total records!

Willie Nelson onstage in 1962
Willie Nelson, age 29, onstage in 1962Getty

Over time, Nelson became celebrated as an artist in his own right, rather than just a songwriter for other singers, but he wasn’t happy with all of his early albums as a clean-cut crooner, writing, “I was holding back my rebellious spirit in the hope that going along with the label’s program would get me somewhere.”

Country singer/songwriter Willie Nelson poses for a portrait in circa 1965
Willie Nelson, age 32, in 1965Getty

As he put it, in the ’60s he had “no image to speak of,” and while he built up a reputation as a talented young singer/songwriter, Nelson wouldn’t become the long-haired star we know and love today until the next decade.

Country singer/songwriter Willie Nelson poses for a portrait with an electric guitar in circa 1967
Willie Nelson, age 34, in 1967Getty

A ’70s country icon

By the ’70s, Nelson was already a veteran performer, and he kept up a fast pace, releasing two albums a year from 1970 to 1972. However, he felt these albums didn’t show his full potential and wanted to let his rebellious side take the lead.

Country singer/songwriter Willie Nelson performs onstage at the Palomino Club on May 8, 1970 in Los Angeles, California
Willie Nelson, age 37, onstage in 1970Getty

Nelson’s 1973 album Shotgun Willie was a shift in an edgier direction and earned rave reviews, with Rolling Stone writing, “At the age of 39, Nelson finally seems destined for the stardom he deserves.”

Country singer/songwriter Willie Nelson poses for a portrait wearing a cowboy hat in circa 1973
Willie Nelson, age 40, in 1973Getty

As Nelson entered his 40s, he began growing out his hair and sporting a beard, developing the instantly recognizable look he still proudly rocks today. In 1975, the album Red Headed Stranger became his first to hit number 1 on the country charts, and it was certified platinum.

Country music singer-songwriter Willie Nelson promotes his "Red Headed Stranger" album at Peaches Records and leaves his footprints in concrete on October 28, 1975 in Atlanta, Georgia
Willie Nelson, age 42, in 1975Getty

Red Headed Stranger is one of Nelson’s most famous albums, but as he remembered, “When I turned it in, the suits hated it. Said it sounded tinny and unfinished. Said the combination of old songs and new ones was confusing. Said it wouldn’t sell.”

Nelson was undeterred, and knew he had something special on his hands. He proved the suits wrong as “it sold like hotcakes,” and for the rest of the decade, he cranked out one hit album after another, all filled with songs that embodied his outlaw spirit.

Country singer/songwriter Willie Nelson poses for a portrait in circa 1977
Willie Nelson, age 44, in 1977Getty

Willie Nelson young was not yet a hippie bad boy, and it’s fascinating to realize that he didn’t land on his distinctive style until he was pushing 40. The country is proof that it can take a while to find your signature aesthetic and sound, but when you do, it’s worth holding on to for decades.


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