Waylon Jennings

The Outlaw Country Legend; Music History, Albums & Legacy

Waylon Jennings was one of the most influential figures in country music history and a founding force behind the Outlaw Country movement of the 1970s. Known for his deep voice, rebellious attitude and that Flying W logo, Jennings helped redefine what country music was by relentlessly pushing for artistic independence and spearheading a rawer, more authentic sound.

Waylon was born in Texas in 1937, first working as a radio DJ before getting a break as a touring musician on Buddy Holly’s doomed “Winter Dance Party” tour, where he gave up his seat on Buddy Holly’s ill-fated flight.

Throughout the 1970s and 1980s, Jennings recorded a string of legendary albums including Honky Tonk Heroes, Dreaming My Dreams, Are You Ready for the Country, and Ol’ Waylon. His music, style and attitude helped define outlaw country alongside artists like Willie Nelson and Kris Kristofferson.

Today Waylon Jennings remains one of the most respected figures in country music.

“Are you sure ol’ Hank done it this way?”
– Waylon Jennings

Frequently Asked Questions about Waylon Jennings

Who was Waylon Jennings?

Waylon Jennings was an American country music singer, songwriter and guitarist who became one of the leading voices of the Outlaw Country movement in the 1970s. Known for his deep voice, rebellious attitude and independent spirit, Jennings helped redefine country music by breaking away from Nashville’s traditional studio system.

What is the Flying W logo and When was it first used?

The Flying W is the iconic logo associated with Waylon Jennings was first used in about 1978 on the back of Waylon’s “I’ve Always Been Crazy” album. The winged “W” is supposed to invoke an eagle imagery, and became a signature symbol of Jennings’ music and the outlaw country movement, appearing on albums, tour posters and merchandise throughout his life and far beyond.

What Was Waylon Jennings’ part in the Outlaw Country movement?

Waylon Jennings was one of the “founders” of the Outlaw Country movement alongside artists like Willie Nelson and Kris Kristofferson. In the 1970s this group of musicians pushed back at their labels for artistic independence and a rawer sound that was more their own.

They challenged the “Nashville” way of doing country music, which controlled a lot of artists’ creative decisions, and was highly polished in the studio with the express intent of commercial radio play. Waylon, Willie, Johnny Cash had first tried to make it in Nashville at the same time (Waylon and Cash were even roommates once), and couldn’t abide by the style.

So each rejected Nashville and set out on their own in search of an audience. By 1977, they’d paved their own way in country music, and people were calling it Outlaw Country, a sort of tongue-in-cheek reference to being “outlawed” from Nashville.

What are Waylon Jennings’ most famous songs?

Waylon Jennings recorded classic country songs including Luckenbach, Texas, Mammas Don’t Let Your Babies Grow Up to Be Cowboys, and Are You Sure Hank Done It This Way. Waylon’s music blended traditional country roots with a rebellious outlaw attitude. He had 16 number one hits and 11 number one albums in his career.

What are Waylon Jennings’ most famous albums?

Just a few of Waylon Jennings’ most influential albums are below, these albums helped define the outlaw country sound.

Honky Tonk Heroes (1973)
Dreaming My Dreams (1975)
Are You Ready for the Country (1976)
Ol’ Waylon (1977)

Did Waylon Jennings know Buddy Holly?

Yes. Waylon’s first touring musician job was on Buddy Holly’s doomed tour. Jennings famously gave up his seat on Holly’s chartered plane before the tragic 1959 crash that killed Holly, Ritchie Valens and The Big Bopper.

Waylon Jennings Articles & Trivia: Learn about Ol’ Waylon

Discover interesting stories behind Waylon Jennings’ most legendary moments, songs, and albums. These are longer-form trivia and history articles about Waylon topics that deserve more than a trivia one-liner.

The Story of Waylon Jennings escaping fate on Buddy Holly’s doomed plane

What Is Outlaw Country?

Waylon Jennings’ “Are You Sure Hank Done It This Way” Song Facts, History & Lyrics

I’ve always felt that blues, rock ‘n’ roll and country are just about a beat apart.
– Waylon Jennings

Waylon Jennings Discography

Waylon at JD’s (1964)
Folk-Country (1966)
Leavin’ Town (1966)
Nashville Rebel (1966)
Waylon Sings Ol’ Harlan (1967)
Love of the Common People (1967)
The One and Only (1967)
Hangin’ On (1968)
Only the Greatest (1968)
Jewels (1968)
Just to Satisfy You (1969)
Waylon (1970)
Singer of Sad Songs (1970)
The Taker / Tulsa (1971)
Cedartown, Georgia (1971)
Good Hearted Woman (1972)
Ladies Love Outlaws (1972)
Lonesome, On’ry and Mean (1973)
Honky Tonk Heroes (1973)
This Time (1974)
The Ramblin’ Man (1974)
Dreaming My Dreams (1975)
Are You Ready for the Country (1976)
Ol’ Waylon (1977)
I’ve Always Been Crazy (1978)
What Goes Around Comes Around (1979)
Music Man (1980)
Black on Black (1982)
Waylon and Company (1983)
Never Could Toe the Mark (1984)
Turn the Page (1985)
Will the Wolf Survive (1986)
Hangin’ Tough (1987)
A Man Called Hoss (1987)
Full Circle (1988)
The Eagle (1990)
Too Dumb for New York City, Too Ugly for L.A. (1992)
Waymore’s Blues, Part II (1994)

Collaborations with Willie Nelson

Waylon & Willie (1978)
WWII (1982)
Take It to the Limit (1983)
Clean Shirt (1991)

The Highwaymen (with Willie Nelson, Johnny Cash, and Kris Kristofferson)

Highwayman (1985)
Highwayman 2 (1990)
The Road Goes On Forever (1995)

Live Albums

Waylon Live (1976) (Live)
Waylon Live: Expanded Edition (1976) (Live)
Live from Austin, TX (1989) (Live)
Never Say Die: Live (2000) (Live)
Waylon Jennings Live at the US Festival (1983) (Live)
Live: American Outlaws (2016) (with The Highwaymen)

Without [Waylon] Jennings and his ground-breaking separation from the Nashville country machine, artists like me would not be able to make the music we do.
– Steve Earle

Featured Waylon Jennings T-Shirts & Merch

Waylon Jennings Lonesome Onry & Mean T-Shirt – Lightweight Vintage Style
Price range: $34.95 through $38.95 Select options This product has multiple variants. The options may be chosen on the product page
Select options This product has multiple variants. The options may be chosen on the product page Quick View Add to wishlist
Are You Sure Hank Done It This Way Waylon Jennings T-Shirt – Lightweight Vintage Style
Price range: $34.95 through $38.95 Select options This product has multiple variants. The options may be chosen on the product page
Select options This product has multiple variants. The options may be chosen on the product page Quick View Add to wishlist
Waylon Jennings Guitar T-Shirt – Lightweight Vintage Style
Price range: $34.95 through $38.95 Select options This product has multiple variants. The options may be chosen on the product page
Select options This product has multiple variants. The options may be chosen on the product page Quick View Add to wishlist
Waylon Jennings Black on Black T-Shirt – Lightweight Vintage Style
Price range: $34.95 through $38.95 Select options This product has multiple variants. The options may be chosen on the product page
Select options This product has multiple variants. The options may be chosen on the product page Quick View Add to wishlist

Waylon was the only one of us who really deserved the ‘Outlaw’ title. He fought for his music, he fought for his friends, and he usually won.
– Johnny Cash

Waylon Jennings Trivia & Quotes

“Down in Texas, they think when they die, they go to Willie’s house.” – Waylon Jennings

“The only two things in life that make it worth livin’ Is guitars that tune good and firm feelin’ women” – Waylon Jennings, “Luckenbach, Texas (Back To The Basics Of Love)”

“I’m just a man, no more no less. Bad as the worst, good as the rest.” – Waylon Jennings

Waylon Jennings and Johnny Cash were once roommates in a rented apartment in Nashville.

“Ain’t living long like this… Can’t live at all like this, can I baby?” – Waylon Jennings

“Let’s go to Luckenbach, Texas With Waylon and Willie and the boys” – Waylon Jennings, “Luckenbach, Texas (Back To The Basics Of Love)”

Willie Nelson’s “Shotgun Willie”, Waylon Jennings’ “Honky Tonk Heroes”, and Billy Joe Shaver’s “Old Five and Dimers Like Me” were all released in 1973, cementing Outlaw Country music as a genre.

“Here comes the ‘tra la la'” – Waylon Jennings

“Are you sure ol’ Hank done it this way?” – Waylon Jennings

Notable Waylon Jennings Live Videos

Waylon at Austin City Limits in 1984

This is Waylon Jennings performing "I Ain't Living Long Like This" for Austin City Limits with The Waylors and Ralph Mooney on pedal steel guitar. It was taped for the opening of ACL's tenth season. It was released as a DVD called "Live from Austin Texas"

Waylon playing Are You Sure Hank Done It This Way

Waylon Jennings performing his classic "Are You Sure Hang Done It That Way" live at the US Festival, 1983. Waylon appeared at the US Festival on June 4, 1983, on the bill with Willie Nelson, Alabama, Hank Williams, Jr., and Emmylou Harris, and Jennings' wife Jessi Colter, who did a duet "Storms Never Last."

Waylon's Last Performance

This is the full concert of Waylon Jennings’ last major performance, at the historic Ryman Auditorium in Nashville, two years before he died. This is Waylon Jennings & The Waymore Blues Band in high resolution at the Grand Ole Opry.