Waylon Jennings: The original outlaw, and one of the greatest country heros of all time, Jennings was born and raised in Littlefield, TX, where he learned how to play guitar by the time he was eight. When he was 12 years old, he was a DJ for a local radio station and, shortly afterward, formed his first band. His style evolved over time, taking on a tougher, more bass-driven sound. He befriended such artists as Willie Nelson, and formed the Highwaymen with Nelson, Johnny Cash, and Kris Kristofferson in 1985. Between 1966 and 1995, 54 Jennings albums charted, with 11 reaching number one. Meanwhile between 1965 and 1991, 96 singles charted, with 16 number ones. In October 2001, Jennings was inducted into the Country Music Hall of Fame. In one final act of defiance, he did not attend the ceremony and opted instead to send son Buddy Dean Jennings. Waylon passed away on February 13, 2002, but his spirit lives on in all of those that he has inspired.