Willie Nelson remains one of the most fascinating figures in music.

While he may be known by millennials for his hokey country tunes and unbridled passion for marijuana legalization, Nelson has actually led one of the most fascinating lives in pop culture. Now one of the most important singers of the 20th century, he actually got his start as a DJ in California in the 1950s spinning Country records. From there, Nelson went on to play bass in a band led by country legend Ray Price and helped Price curate some of the biggest country hits of the 1960s. This was all before he went on to personally spearhead the "outlaw music" subgenre and explode as one of the most exciting voices in country music. His sound was revolutionary, a casual singing style that at times bordered on being offbeat, Nelson's detailed, and often slightly bizarre, narratives contained within some of his biggest songs are charismatic, reflective, and funny, a refreshing change from the stiff earnestness of country acts at the time. From his unbridled belief in marijuana legalization and passion for avoiding the IRS, Nelson's identity has always been colorful, to say the least.