33 Outlaw Country Stars Who Lived By Their Own Rules

Carly Tennes Published 08/28/2024 in wow

Long before Luke Combs, Miranda Lambert, and Morgan Wallen emerged as the modern faces of country music, the genre was a whole lot more rugged. Enter legendary artists like Johnny Cash, Willie Nelson, Merle Haggard, and Kris Kristofferson, legends who put grit and soul into the music that defined middle-America.

From smoke-fueled studio sessions to performances at the Grand Ole Opry, here are 33 Nostalgic pics of your favorite outlaw country stars.

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1.
“Waylon Jennings, 1979, after just receiving Buddy Holly's motorcycle for his 42nd birthday. The original Crickets tracked down Buddy's motorcycle, bought it from the man, and gave it to Waylon. It's a 1958 Ariel Cyclone.”
2.
“Waylon Jennings & Willie Nelson backstage in the 70s.”
3.
“Waylon Jennings and Johnny Cash, 1974.”
4.
“Waylon Jennings & Buddy Holly, 1959.”
5.
“Waylon Jennings and Willie Nelson at Willie’s Fourth of July Picnic in 1973.”
6.
“Waylon Jennings, 1970.”
7.
“Waylon Jennings, 1973.”
8.
“‘The Highwaymen’ - Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson, 1985.”
9.
“The Highwaymen, Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash, 1985.”
10.
“Kris Kristofferson in ‘Convoy’ (1978).”
11.
“Kris Kristofferson, Willie Nelson and Waylon Jennings, Dripping Springs Festival, Texas 1972.”
12.
“Kris Kristofferson pouring himself a beer for breakfast (1970s).”
13.
“Stevie Ray Vaughan, Bonnie Raitt and Kris Kristofferson in 1980s.”
14.
“Merle Haggard at the Opry (1980).”
15.
“Merle Haggard, 1970s.”
16.
“Rita Coolidge and Kris Kristofferson in 1973.”
17.
“Merle Haggard in the late 1960’s.”
18.
“Johnny Cash shaking an inmate's hand at Folsom State Prison, California (1968)”
19.
Johnny Cash stands outside of Folsom Prison.
20.
Johnny Cash in what appears to be a studio, date unknown.
21.
John Cash during what appears to be a nicotine-fueled writing session, date unknown.
22.
Johnny Cash lights up a cigarette, date unknown.
23.
Kris Kristofferson strums a guitar, 1971.
24.
Kris Kristofferson puffs away at a banquet, 1972.
25.
Kris Kristofferson and his wife, Rita Coolidge, enjoy a snack before taking the stage at the Grand Ole Opry, 1972.
26.
Kris Kristofferson and Roger Miller rock out at Vanderbilt, 1972.
27.
Merle Haggard performs with Johnny Cash on The Johnny Cash Show, 1969.
28.
Merle Haggard meets then-President Richard Nixon, 1973.
29.
“Merle Haggard as cool as ever.”
30.
“Willie Nelson in 1960.”
31.
“Waylon Jennings & Willie Nelson 1974.”
32.
“Willie Nelson at the White House in 1977.”
33.
The Highwaymen hit the stage, October 1985.

1.
“Waylon Jennings, 1979, after just receiving Buddy Holly's motorcycle for his 42nd birthday. The original Crickets tracked down Buddy's motorcycle, bought it from the man, and gave it to Waylon. It's a 1958 Ariel Cyclone.”
2.
“Waylon Jennings & Willie Nelson backstage in the 70s.”
3.
“Waylon Jennings and Johnny Cash, 1974.”
4.
“Waylon Jennings & Buddy Holly, 1959.”
5.
“Waylon Jennings and Willie Nelson at Willie’s Fourth of July Picnic in 1973.”
6.
“Waylon Jennings, 1970.”
7.
“Waylon Jennings, 1973.”
8.
“‘The Highwaymen’ - Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson, 1985.”
9.
“The Highwaymen, Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash, 1985.”
10.
“Kris Kristofferson in ‘Convoy’ (1978).”
11.
“Kris Kristofferson, Willie Nelson and Waylon Jennings, Dripping Springs Festival, Texas 1972.”
12.
“Kris Kristofferson pouring himself a beer for breakfast (1970s).”
13.
“Stevie Ray Vaughan, Bonnie Raitt and Kris Kristofferson in 1980s.”
14.
“Merle Haggard at the Opry (1980).”
15.
“Merle Haggard, 1970s.”
16.
“Rita Coolidge and Kris Kristofferson in 1973.”
17.
“Merle Haggard in the late 1960’s.”
18.
“Johnny Cash shaking an inmate's hand at Folsom State Prison, California (1968)”
19.
Johnny Cash stands outside of Folsom Prison.
20.
Johnny Cash in what appears to be a studio, date unknown.
21.
John Cash during what appears to be a nicotine-fueled writing session, date unknown.
22.
Johnny Cash lights up a cigarette, date unknown.
23.
Kris Kristofferson strums a guitar, 1971.
24.
Kris Kristofferson puffs away at a banquet, 1972.
25.
Kris Kristofferson and his wife, Rita Coolidge, enjoy a snack before taking the stage at the Grand Ole Opry, 1972.
26.
Kris Kristofferson and Roger Miller rock out at Vanderbilt, 1972.
27.
Merle Haggard performs with Johnny Cash on The Johnny Cash Show, 1969.
28.
Merle Haggard meets then-President Richard Nixon, 1973.
29.
“Merle Haggard as cool as ever.”
30.
“Willie Nelson in 1960.”
31.
“Waylon Jennings & Willie Nelson 1974.”
32.
“Willie Nelson at the White House in 1977.”
33.
The Highwaymen hit the stage, October 1985.

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“Waylon Jennings, 1979, after just receiving Buddy Holly's motorcycle for his 42nd birthday. The original Crickets tracked down Buddy's motorcycle, bought it from the man, and gave it to Waylon. It's a 1958 Ariel Cyclone.”

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Categories: Wow History Music

Tags: country_music old_school the_highwaymen johnny_cash willie_nelson merle_haggard kris_kristofferson

NEXT GALLERY 40 People Having a Worse Day Than You

1. “Waylon Jennings, 1979, after just receiving Buddy Holly's motorcycle for his 42nd birthday. The original Crickets tracked down Buddy's motorcycle, bought it from the man, and gave it to Waylon. It's a 1958 Ariel Cyclone.”

2. “Waylon Jennings & Willie Nelson backstage in the 70s.”

3. “Waylon Jennings and Johnny Cash, 1974.”

4. “Waylon Jennings & Buddy Holly, 1959.”

5. “Waylon Jennings and Willie Nelson at Willie’s Fourth of July Picnic in 1973.”

6. “Waylon Jennings, 1970.”

7. “Waylon Jennings, 1973.”

8. “‘The Highwaymen’ - Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson, 1985.”

9. “The Highwaymen, Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash, 1985.”

10. “Kris Kristofferson in ‘Convoy’ (1978).”

11. “Kris Kristofferson, Willie Nelson and Waylon Jennings, Dripping Springs Festival, Texas 1972.”

12. “Kris Kristofferson pouring himself a beer for breakfast (1970s).”

13. “Stevie Ray Vaughan, Bonnie Raitt and Kris Kristofferson in 1980s.”

14. “Merle Haggard at the Opry (1980).”

15. “Merle Haggard, 1970s.”

16. “Rita Coolidge and Kris Kristofferson in 1973.”

17. “Merle Haggard in the late 1960’s.”

18. “Johnny Cash shaking an inmate's hand at Folsom State Prison, California (1968)”

19. Johnny Cash stands outside of Folsom Prison.

20. Johnny Cash in what appears to be a studio, date unknown.

21. John Cash during what appears to be a nicotine-fueled writing session, date unknown.

22. Johnny Cash lights up a cigarette, date unknown.

23. Kris Kristofferson strums a guitar, 1971.

24. Kris Kristofferson puffs away at a banquet, 1972.

25. Kris Kristofferson and his wife, Rita Coolidge, enjoy a snack before taking the stage at the Grand Ole Opry, 1972.

26. Kris Kristofferson and Roger Miller rock out at Vanderbilt, 1972.

27. Merle Haggard performs with Johnny Cash on The Johnny Cash Show, 1969.

28. Merle Haggard meets then-President Richard Nixon, 1973.

29. “Merle Haggard as cool as ever.”

30. “Willie Nelson in 1960.”

31. “Waylon Jennings & Willie Nelson 1974.”

32. “Willie Nelson at the White House in 1977.”

33. The Highwaymen hit the stage, October 1985.

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eBaum's Picks

1.
“Waylon Jennings, 1979, after just receiving Buddy Holly's motorcycle for his 42nd birthday. The original Crickets tracked down Buddy's motorcycle, bought it from the man, and gave it to Waylon. It's a 1958 Ariel Cyclone.”

2.
“Waylon Jennings & Willie Nelson backstage in the 70s.”

3.
“Waylon Jennings and Johnny Cash, 1974.”

4.
“Waylon Jennings & Buddy Holly, 1959.”

5.
“Waylon Jennings and Willie Nelson at Willie’s Fourth of July Picnic in 1973.”

6.
“Waylon Jennings, 1970.”

7.
“Waylon Jennings, 1973.”

8.
“‘The Highwaymen’ - Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson, 1985.”

9.
“The Highwaymen, Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash, 1985.”

10.
“Kris Kristofferson in ‘Convoy’ (1978).”

11.
“Kris Kristofferson, Willie Nelson and Waylon Jennings, Dripping Springs Festival, Texas 1972.”

12.
“Kris Kristofferson pouring himself a beer for breakfast (1970s).”

13.
“Stevie Ray Vaughan, Bonnie Raitt and Kris Kristofferson in 1980s.”

14.
“Merle Haggard at the Opry (1980).”

15.
“Merle Haggard, 1970s.”

16.
“Rita Coolidge and Kris Kristofferson in 1973.”

17.
“Merle Haggard in the late 1960’s.”

18.
“Johnny Cash shaking an inmate's hand at Folsom State Prison, California (1968)”

19.
Johnny Cash stands outside of Folsom Prison.

20.
Johnny Cash in what appears to be a studio, date unknown.

21.
John Cash during what appears to be a nicotine-fueled writing session, date unknown.

22.
Johnny Cash lights up a cigarette, date unknown.

23.
Kris Kristofferson strums a guitar, 1971.

24.
Kris Kristofferson puffs away at a banquet, 1972.

25.
Kris Kristofferson and his wife, Rita Coolidge, enjoy a snack before taking the stage at the Grand Ole Opry, 1972.

26.
Kris Kristofferson and Roger Miller rock out at Vanderbilt, 1972.

27.
Merle Haggard performs with Johnny Cash on The Johnny Cash Show, 1969.

28.
Merle Haggard meets then-President Richard Nixon, 1973.

29.
“Merle Haggard as cool as ever.”

30.
“Willie Nelson in 1960.”

31.
“Waylon Jennings & Willie Nelson 1974.”

32.
“Willie Nelson at the White House in 1977.”

33.
The Highwaymen hit the stage, October 1985.