Nelson got his first guitar at the early age of six and soon started writing his own songs. A few years later, he played his first professional gig with a local polka band. Nelson later joined Bud Fletcher and the Texans and played the local club circuit. Also in the group was his sister Bobbie, who played piano. She later married Bud Fletcher. One of his early inspirations was Bob Wills and His Texas Playboys—a group known for their upbeat country dance music, which included some elements of swing.
After graduating high school in 1950, Nelson went into the U.S. Air Force. He did not last long, however. Stationed in Lackland in San Antonio, Texas, Nelson had to leave the service because of back problems. He tried college, attending Baylor University for a time. To make ends meet, Nelson took on odd jobs, including selling encyclopedias door to door.
Dropping out, Nelson worked as a radio disc jockey for several years and played gigs in his spare time. He continued writing songs, producing some of his most famous works—inclucing "Night Life," "Crazy," and "Funny How Time Slips Away"—in the late 1950s.
In 1960, Nelson moved to the country music capital: Nashville, Tennessee. He got a job as a songwriter for Pamper Music, earning about $50 a week. The next year, two of Nelson's songs become hits for other artists—Faron Young's version of "Hello Walls" and Patsy Cline's legendary rendition of "Crazy." His first album was released the next year without generating much notice.
Singer Ray Price, with whom Nelson had played with previously, made Nelson's song "Night Life" a big hit in 1963. It seemed that his songs were only successful when they were sung by other people. With his gritty, road house sound, Nelson did not fit into the traditional Nashville country music scene. Producers tried to make him fit the more classic country mould, but they just stripped away his unique style, such as his unusual manner of phrasing. And his resistance to these efforts made him a bit of an outlaw, as did his reputation as a hard-drinking, hard-living man.
His home in Ridgetop, Tennessee, burnt down in 1970. Taking this as a sign, Nelson moved away from Nashville, returning to his native state of Texas. He became part of the country music scene in Austin and started hosting his now legendary Fourth of July picnics. Inspired by Woodstock, the gatherings became popular musical celebrations, and included performances from other country music outlaws such as Kris Kristofferson and Waylon Jennings.
Nelson also kept recording albums, but now he was definitely going his own way. Soon the long haired, bandana-wearing guitarist started to develop a following. Shotgun Willie (1973) is considered to be one of his greatest albums of all time, and showcased his abilities as a singer, storyteller, and performer. The next year, Nelson released Phases and Stages (1974), which became another popular album for the rising star.
With his album, Red Headed Stranger (1975), Nelson had his first taste of crossover success. It did well on both the country and rock charts and featured the hit "Blue Eyes Crying in the Rain," which was written by Fred Rose. Along with being his first song to reach No. 1 on the country charts, the song also brought Nelson his first Grammy Award for Best Country Vocal Performance in 1975.
Around this time, he contributed to the compilation Wanted: The Outlaws, which also featured Waylon Jennings, Jessi Colter, and Tompall Glaser. Nelson and Jennings also collaborated on the popular song "Mamas Don't Let Your Babies Grow Up To Be Cowboys," which won the 1978 Grammy Award for Best Country Vocal Performance by a Duo or Group.
Always interested in different music styles, Nelson recorded his own takes on some American standards on his album Stardust (1978). His cover of Hoagy Carmichael and Stuart Gorrell's "Georgia on My Mind" earned him his second Grammy Award for Best Country Vocal Performance. Beyond its critical success, the album proved to have staying power as well, lingering on the country charts for a decade.
Around this time, Nelson also branched out into acting. He first appeared in The Electric Horseman (1979) starring Robert Redford. Soon after, Nelson starred in Honeysuckle Rose (1980), in which he played a veteran country musician performer. His character was torn between his wife (played by Dyan Cannon) and the young singer (Amy Irving) who joins him on the road. The film also featured the song "On the Road Again," which earned Nelson an Academy Award nomination for Best Original Song. Now considered a trademark Nelson tune, "On the Road Again" also won the Grammy Award for Best Country Song in 1980.
Nelson's successful streak—both commercially and critically—continued into the 1980s. The ballad "Always on my Mind" won the Grammy Award for Best Country Vocal Performance in 1982. Albums Without A Song (1984) and City of New Orleans (1984) reached the top or near the top of the country charts. Singing with singer Julio Iglesias, Nelson scored a big hit with the ballad "To All the Girls I've Loved Before" in 1984.
The following year, Nelson teamed up with Johnny Cash, Waylon Jennings, and Kris Kristofferson to form the Highwaymen. Their first release, Highwayman (1985) was a big hit, as was the title track. The group went on to produce a live album and another studio effort, Highwayman 2 (1995).
Known for his compassion, Nelson—along with Neil Young and John Mellencamp—organized the first Farm Aid concert in 1985 in an effort to help family farmers. To date, the Farm Aid organization has raised more than $30 million and continues to work to keep family farmers on their land. In 2007, Ben & Jerry's released "Willie Nelson's Country Peach Cobbler Ice Cream" with a portion of Nelson's proceeds donated to Farm Aid.
In 1990, Nelson ran into his own financial problems. The Internal Revenue Service (IRS) told him that he owed the government $16 million in taxes, and they seized most of his property to cover the bill. Maintaining his sense of humor, Nelson released The IRS Tapes: Who'll Buy My Memories to generate some cash to pay off the government.
On a much more personal level, Nelson was dealt another devastating blow when his son Billy committed suicide on Christmas Day in 1991. Still, Nelson managed to keep going and keep recording. Several of his albums, including Across the Borderline (1993) and Healing Hands of Time (1994) reached the top 20 on the country album charts.
Known for smoking marijuana, Nelson was arrested in 1994 after pot was found in his car. The case was later thrown out. In 2006, Nelson was again arrest for possession in Louisiana. This time he received six months probation.
That same year, Nelson helped out his hometown of Abbott, Texas. He bought and continues to support the town's church and grocery store, which were both in danger of failing. Nelson has also worked on behalf of the environment, promoting an alternative, cleaner burning fuel known as biodiesel. In 2007, he even started marketing his own brand called BioWillie, which is a combination of diesel and biodiesel made from soybeans. "It seems like that's good for the whole world if we can start growing our own fuel instead of starting wars over it." said Nelson in a 2005 interview.
Not only is he generous with his money, but also his time. Over the years, Nelson has shown a deep commitment to his fans. After a show, "He'll stay there for hours, signing autographs and meeting people," friend Kris Kristofferson told Texas Monthly.
And Nelson shows no signs of slowing down. He still tours heavily, playing approximately 150 to 200 dates a year. Always experimenting, Nelson continues to try out new types of material. In 2005, he released Countryman, which incorporated elements of reggae. Nelson released Moment of Forever in 2008, which garnered much critical praise. He also scored a Grammy that same year for the single "Lost Highway," another of his collaborations with Ray Price. Nelson also performed live in Amsterdam with rap icon Snoop Dogg in May of 2008. The duo have since work together on several projects, including the video "My Medicine."
In February 2009, Willie Nelson teamed up with music group Asleep at the Wheel to release the country swing album entitled Willie and the Wheel. In March, he released his latest solo effort entitled Naked Willie. The album includes remixes of his early recordings. He also continues to perform live into 2009 with his "On the Road Again" tour.
Nelson also appeared on the big screen in more films such as Surfer Dude (2008), Shoot Out of Luck (2008), Beer for My Horses (2008) and The Boom Boom Room (2008).
In his personal life, Nelson has seen many ups and downs. He married Martha Matthews in 1952, and they had three children together, Lana, Susie, and Billy, before splitting up. In 1963, Nelson married singer Shirley Collie, but he divorced her to be with Connie Koepke. They had two daughters, Paula and Amy. Willie and Connie divorced in 1988 after Willie became involved with Ann Marie "Annie" D'Angelo. Nelson married D'Angelo in 1991 and they have been together ever since. They have two sons, Lucas and Jacob Micah.