Happy birthday, Willie Nelson! The singer turns 85 on April 29.

These days, Nelson is known for his beard and long double braids, but before he became an icon of “outlaw” country music, he was a clean-cut teen at Abbott High School in Abbott, Texas.

He looks almost unrecognizable as a high school junior in this 1949 yearbook photo.

Nelson was also a dedicated high school athlete. He was a halfback on the football team and played on the basketball and baseball teams. Here’s Nelson’s official football portrait from around 1950:

While in school, Nelson sang for money in local taverns and dance halls.

“When I was about 12, I had my first paying gig,” the singer told Parade in 2010. “Eight dollars to play rhythm guitar in a polka band. Pretty soon, I ended up playing in all the bars within driving distance of Abbott, Texas.”

He also reportedly had various odd jobs including tree trimmer, pawn shop employee and phone operator. Still, he never lost sight of his dream career.

“Since I was a kid, music was what I wanted to do,” Nelson told Parade. “I thought I could make it by my own talents. That’s what I wanted to prove.”