1 of 32 Johnny Cash poses for a mugshot after U.S. Customs agents found hundreds of pep pills & tranquilizers in his luggage as he returned to El Paso, Texas from a trip to Juarez, Mexico in 1965. Michael Ochs Archives/Getty Images

2 of 32 Willie Nelson and Waylon Jennings enjoy a drink together in New York. 1978. Richard E. Aaron/Redferns/Getty Images

3 of 32 Waylon Jennings poses with a pistol. YouTube

4 of 32 Johnny Paycheck holds a Teamsters union sign while joining a group of striking bookbinders. 1977. Hulton Archive/Getty Images

5 of 32 Charlie Daniels sits backstage with a bottle of booze at the Uptown Theater in Chicago, Illinois. 1978. Kirk West/Getty Images

6 of 32 Johnny Cash straddles railroad tracks, guitar in hand. 1969. Michael Rougier/The LIFE Picture Collection/Getty Images

7 of 32 Mugshot of Willie Nelson after he was arrested for speeding and driving without a license in Pasadena, Texas. 1960. Wikimedia Commons

8 of 32 Mugshot of Willie Nelson after he was arrested in 1974 by Dallas police for possession of marijuana. Wikimedia Commons

9 of 32 Waylon Jennings, Jessi Colter, and Rosalynn Carter at a reception preceding a concert to benefit the Carter-Mondale campaign in 1980 Wikimedia Commons

10 of 32 Country singer Merle Haggard in a candid portrait taken in the early 1970s. Michael Ochs Archives/Getty Images

11 of 32 Johnny Cash chats with some of the inmates and guests during his visit to Cummins Prison in Arkansas. 1969. Bettmann/Getty Images

12 of 32 Waylon Jennings, drink in hand, goes in for a kiss. 1973. Michael Ochs Archives/Getty Images

13 of 32 Willie Nelson (left) and actor/comedian John Belushi hang out at the Lone Star Cafe in New York City after Nelson's first T.V. appearance on Saturday Night Live. 1977. Stephanie Chernikowski/Redferns/Getty Images

14 of 32 Mugshot of David Allan Coe before he served three years in the Ohio State Penitentiary. Ohio State Police Department

15 of 32 Hank Williams, Jr. sits at home with hunting trophies and a portrait showing him in Montana, where he almost died in a fall during a mountain climbing expedition. 1977. Bettmann/Getty Images

16 of 32 Singer Tanya Tucker in the late 1970s. Michael Ochs Archives/Getty Images

17 of 32 Charlie Daniels in Australia. Circa 1970. GAB Archive/Redferns/Getty Images

18 of 32 Pioneering rock and roller Buddy Holly and Waylon Jennings pose together in a photo booth. 1958. Personal photo

19 of 32 Waylon Jennings (center) enjoys pre-race festivities before an NASCAR race. 1972. ISC Images and Archives/Getty Images

20 of 32 Kris Kristofferson, as seen in a publicity photo. 1978. Wikimedia Commons

21 of 32 David Allen Coe speaks with several police officers. Date unspecified. David Allen Coe

22 of 32 Waylon Jennings performs on stage. Circa 1970. Michael Ochs Archives/Getty Images

23 of 32 Billy Joe Shaver stands outside near Wise Fool's Pub in Chicago, Illinois. 1980. Kirk West/Getty Images

24 of 32 Johnny Cash sits in the driver's seat of a Cadillac. Date unspecified. Wikimedia Commons

25 of 32 Sammi Smith performs on stage. Circa 1970s. Michael Ochs Archives/Getty Images

26 of 32 Johnny Paycheck (left) and Merle Haggard sit at the Countryside Opry in, Chicago, Illinois. 1980. Kirk West/Getty Images

27 of 32 Tompall Glaser poses for a portrait. 1977. Michael Ochs Archives/Getty Images

28 of 32 Kris Kristofferson poses with his guitar. 1970. Michael Ochs Archives/Getty Images

29 of 32 Billy Joe Shaver (left) poses at Wise Fool's Pub in Chicago, Illinois. 1980. Kirk West/Getty Images

30 of 32 Ed Bruce sits backstage at Phoenix in Chicago, Illinois. 1980. Kirk West/Getty Images

31 of 32 Willie Nelson takes a drink backstage. Date unspecified. Wally McNamee/Corbis/Getty Images