Waylon Jennings was born in Littlefield, TX, and by the age of 12, he was a disc jockey on local radio. He moved to Lubbock, TX where he met Buddy Holly, and toured with Holly on the ill-fated "Winter Dance Party" tour in 1959, giving up his seat on the fatal plane ride that took the lives of Holly, Big Bopper, and Ritchie Valens. He established himself in the mid-70s as a leader of the "outlaw movement" in country music. Here are the ten albums every Waylon fan should have in their collection.
1. Wanted! The Outlaws
The "Outlaws." Waylon & Willie. Waylon & Jessi. Tompall Glaser. The immortal "My Heroes Have Always Been Cowboys." The eloquent writing of Willie Nelson on "Me and Paul"; Jessi Colter's plaintive little-girl voice; Tompall Glaser's rowdy attitude; and the golden baritone of Waylon Jennings. In 1976, this album made country music history by being the first country album to ever make platinum (one million sales).2. Waylon & Willie
The 'Waylon & Willie' release of 1978 is one of the best-selling albums for either artist, even years later. The album went to the top of the charts and stayed there for 11 weeks. It contains five duets between the two, and three solo songs a piece.3. Greatest Hits
When Waylon Jennings' Greatest Hits was released, Ol' Hoss was at the top, running his own music and fronting the "Outlaw" movement, although Waylon himself had a few choice words to say about that. There are only 9 tracks on "Greatest Hits," but they're 9 of the greatest country songs ever recorded, including anthems like "Mamas Don't Let Your Babies Grow Up to Be Cowboys" and "Are You Sure Hank Done It This Way?" This is also the only place to get Waylon's original recording of "Amanda."4. Never Say Die: Live
Waylon proves that he has still got "it." From the attitude-infused performance that opens the album "Closin' In On The Fire," to the softness in his voice as he sings "Amanda/Couple More Years."5. Honky Tonk Heroes
Waylon Jennings officially became an "outlaw" with this album. He bucked the Nashville system and took control of his own music, choosing his own musicians and producing his own music. He chose for this first effort the songs of Texas songwriter Billy Joe Shaver, who's become a legend in his own right. Together Jennings and Shaver put together an album of almost indescribable perfection, and the right start to a whole new era of country music.6. The Ramblin' Man
Waylon Jennings's iconic voice and characteristic hard-line attitude comes across strongly in this disc, a whirl of hard-hitting emotions and packed with powerful melodies, including three bonus tracks not on the original vinyl. There are two number one hits, the title track and the lilting waltz, "Amanda," as well as the #2 charter, "Rainy Day Woman." In addition, the album itself remained on the country charts for nine months. "The Ramblin' Man" is one terrific album from ol' Hoss.
7. I've Always Been Crazy
Besides the title track and "Don't You Think This Outlaw Bit's Done Got Outta Hand," this album contains covers of a medley of Buddy Holly tunes, a cover of Merle's "Tonight the Bottle Let Me Down," and Johnny Cash's "I Walk the Line."8. Lonesome, On'ry and Mean
Released in 1973, this album contains the title cut, as well as covers of Kris Kristofferson's "Me & Bobby McGee," Mickey Newbury's "San Francisco Mabel Joy," Danny O'Keefe's "Good Time Charlie's Got the Blues," Johnny Cash's "Gone to Denver," and Willie Nelson's "Pretend I Never Happened."9. Dreaming My Dreams
This may be Waylon Jennings' greatest album. In addition to featuring many of his greatest chart hits, it also includes the first great anthem to Texas music, "Bob Wills is Still The King," the iconic live version which dominated the airwaves in the late 70's. The wistful sound of "Dreaming My Dreams With You" or the straightforward in-your-face "Are You Sure Hank Done it This Way" show every side of Waylon Jennings. You want to hear ol' Hoss? This is the disc to do it.10. Only Daddy That'll Walk The Line: The RCA Years (Box set)
This 2-CD set contains 40 of the best of Waylon, from "Love of the Common People," and "Good Hearted Woman," to "Storms Never Last," "Theme from the Dukes of Hazzard (Good Ol' Boys)," and a live version of "Bob Wills Is Still the King." Classic Waylon from his years at RCA.