Willie Nelson struggled to find mainstream country singing success, while serving as one of Nashville's most popular songwriters behind the scenes. It wasn't until Nelson embraced his singular style that he found stardom as the king of outlaw country. Take our quiz to see how much you know about this music legend.
Willie Nelson calls the Lone Star State home. He was born on April 29, 1933 in Abbott, Texas -- where he was raised by his grandparents.
Willie's sister Bobbie has performed with him many times over the years, and she also helped him join his first band. She was dating lead singer Bud Fletcher of Bud Fletcher and the Texans back when brother Willie joined the band in 1947. Bobbie and Bud later married.
Nelson joined the Air Force after graduating from high school in 1950. Due to back problems, he only made it a year before he was honorably discharged from the service.
Nelson attended Baylor University for a couple of years in the mid-'50s as an agriculture major, before dropping out to pursue music.
Willie sold his first song, "Family Bible," for just $50. He used the money to move to Nashville in 1960 to try to make it big in country music.
You may be surprised to learn just how many big country hits Nelson penned as he tried to make it as a singer in Nashville. In addition to Patsy Cline's "Crazy," Nelson wrote "Hello Walls," "Pretty Paper," and "Funny How Time Slips Away."
Nelson's first album, "And Then I Wrote," failed to chart when it was released in 1962. A half-dozen or so other efforts also enjoyed little success throughout the '60s.
After his house burned down in 1970, Willie left Nashville and headed to Austin, Texas. There, he embraced the outlaw country genre and started to find success as a singer for the first time.
After some success at Atlantic Records, Nelson moved to Columbia Records, where he released his first platinum album 'Red Headed Stranger" in 1975. The album went to number one on the country charts and even hit number forty on the pop charts.
Nelson picked up his first Grammy award in 1975. He won the award for Best Country Male Vocal Performance for "Blue Eyes Crying in the Rain."
Nelson played Wendell in "The Electric Horseman" in his film debut. The 1979 Sydney Pollack film also starred Robert Redford and Jane Fonda.
Nelson starred as Buck Bonham, a country star torn between his love for two different women in the 1980 film "Honeysuckle Rose."
When producers asked Nelson to write a song for "Honeysuckle Rose," he put together "On the Road Again." He penned the lyrics for the song on the back of a barf bag while riding on an airplane.
Nelson named his guitar after Roy Rogers' horse, Trigger. Trigger, a Martin N-20, has been by Willie's side since 1969, and has the scars to prove it.
Willie has been married four times, starting back in 1952. He married his fourth wife Ann Marie D'Angelo in 1991. He has seven kids altogether. His son, Willie Jr., committed suicide.
Nelson debuted the iconic "Georgia on My Mind" on his 1978 album, "Stardust," which also featured covers of other pop standards, like "Unchained Melody" and "Someone to Watch Over Me."
In 1979, Willie released "Willie Nelson Sings Kristofferson," an album of Kris' greatest hits. It included Nelson's covers of "Me and Bobby McGee" and "For the Good Times."
In 1963, Nelson wrote the song "Pretty Paper" for Roy Orbison. When Nelson was ready to release his first Christmas album in 1979, he included a cover of the tune and used the title "Pretty Paper" for the album.
Willie Nelson and Waylon Jennings had a smash hit in 1978 with their duet of "Mamas Don't Let Your Babies Grow Up to Be Cowboys." They even won the Grammy for Best Country Vocal Duo or Group for the song.
Nelson's "Always on My Mind" album came out in 1982 and featured the famous title track, as well as covers like "Bridge Over Troubled Water," "A Whiter Shade of Pale" and "Let It Be Me."
Nelson scored big on the pop charts for his 1984 duet with Julio Iglesias. The duo dedicated the song to all the girls they've loved, kissed and caressed.
Willie Nelson teamed up with Kris Kristofferson, Johnny Cash and Waylon Jennings to form The Highwaymen in the '80s. They were inspired to form the group after performing together for a Johnny Cash Christmas show in 1984.
Nelson teamed up with John Mellencamp and Neil Young to hold the first Farm Aid concert in 1985. Since then, the group has raised more than $50 million to support American farmers.
Nelson got in big trouble with the IRS in 1990, learning that he owed one of the biggest past-due tax bills in history. He sold "Who'll Buy My Memories: The IRS Tapes," to pay off a $16 million tax bill.
To celebrate turning 81, Nelson became a fifth-degree black belt in Gongkwon Yusul, a Korean martial art that he had been practicing for more than 20 years.
Willie's 2012 album, "Heroes," featured a host of guest stars, as well as a cover of Coldplay's "The Scientist."
Nelson faced his first arrest for marijuana possession in 1974. He was arrested on similar charges in 2006 and 2010.
Nelson was inducted into the Country Music Hall of Fame in 1993, at the age of 60. He was also inducted into the National Agriculture Hall of Fame in 2011, for his contributions to the field of farming.
In 2004, Wilson introduced BioWillie, a brand of biodiesel made from soybeans and other vegetables. Starting in 2015, he put his name on Willie's Reserve -- a brand of marijuana sold in states where the drug has been legalized.
Willie Nelson has long supported the group NORML -- National Organization for the Reform of Marijuana Laws -- and even serves on the group's board. NORML aims to end federal prohibition against marijuana.