Waylon Jennings passed in 2002 at the age of 64 -- one year after being inducted into the Country Music Hall of Fame. Throughout his career, he remained an honest artist fighting to record the music inside him, the way he wanted to hear it. Jennings' career started in 1958 as when he became a member of Buddy Holly’s Crickets. After Holly’s death, Jennings spread his wings as a solo artist and found a home of his own in country music. We’ve compiled a list of songs that we feel best represents the career of this legendary outlaw -- from popular Willie Nelson duets to the theme from 'The Dukes of Hazard,' to final chart toppers like ‘Wrong’ and ‘Rose in Paradise.’ These are the Top 10 Waylon Jennings songs.

  • 10


    From 'The Eagle' (1990)

    In 1990, Waylon Jennings proved that he still had a few hits left in him, even though by this time he was considered a legend in the music business. The class of '89 -- Garth Brooks, Clint Black, Alan Jackson and Travis Tritt -- were starting to control the charts with the new young country movement at this time, leaving less room for the veterans of the genre. The humorous single accompanied by a comical video gave Waylon Jennings the final Top 5 hit of his career. 'Wrong' is a right way to start our list of the Top 10 Waylon Jennings songs.

  • 9

    'Mamas Don't Let Your Babies Grow Up to Be Cowboys'

    From 'Waylon and Willie' (1978)

    Originally released by its writer Ed Bruce in 1975, 'Mamas Don't Let Your Babies Grow Up to Be Cowboys' was re-recorded by Waylon Jennings and Willie Nelson in 1978. Not only was it a No. 1 hit and Grammy winner, but the chorus is one of the most widely known lyrics in American music. It would be no more a surprise to hear a family singing this song around a campfire than it would be to hear blaring in a crowded honky-tonk.

  • 8

    'Rose in Paradise'

    From 'Hangin' Tough' (1987)

    In 1987, Waylon Jennings landed the final No. 1 of his career with 'Rose in Paradise,' although he would continue to record and tour up until his untimely death in 2002. At the time this song was a hit, Jennings was also riding high as a member of the Highwaymen with his peers Johnny Cash, Willie Nelson, and Kris Kristofferson. Formed in 1985, the quartet launched the first of many tours and three albums together. In 1998, Jennings would also be a part of another super group called the Old Dogs with Mel Tillis, Jerry Reed, Bobby Bare and producer Shel Silverstein.

  • 7

    'Good Hearted Woman'

    From ‘Wanted: The Outlaws’ (1976)

    Waylon Jennings originally recorded this song in 1972, then re-recorded the song as a duet with co-writer Willie Nelson for the ‘Wanted: The Outlaws’ album in 1976. The "outlaw" explosion of the late ‘70s was actually just RCA Records' marketing finally catching up with what Waylon Jennings had been doing for years. Quickly, the conservative country industry accepted hippies, levis and smokers alongside rhinestone-wearing Opry stars. ‘Good Hearted Woman’ is a prime example of a classic "outlaw" hit during this period and a must-have on our list of the Top 10 Waylon Jennings songs.

  • 6

    'Are You Sure Hank Done It This Way?'

    From 'Dreaming My Dreams' (1975)

    In 1975 -- the year Waylon was named the CMA's Male Vocalist of the Year -- he wrote a tribute song to his hero, Hank Williams, Sr. No matter where he played or how many hit songs he had on the radio, Waylon always included at least one Hank Williams song at each concert. Jennings also recorded an entire album of his heroes’ hits on the CD ‘Waylon Sings Hank Williams.’ In 2001, this song was recorded by Alabama for the tribute album ‘Waylon: The Music Inside.’

  • 5


    From 'Waylon’s Greatest Hits, Vol. 2' (1984)

    In 1984, Waylon Jennings sang ‘America’ on a Statue of Liberty restoration television special. The exposure helped the single peak at No. 6 on the Billboard Country charts while earning Song of the Year nominations. The tune was penned by Sammy Johns, known for his 1975 hit ‘Chevy Van.’ Johns also had more country music success by writing the No. 1 hit ‘Desperado Love’ for Conway Twitty. This patriotic classic has a solid placement on our list of the Top 10 Waylon Jennings songs.

  • 4

    'I'm a Ramblin' Man'

    From ‘The Ramblin’ Man’ (1974)

    From the moment Waylon Jennings signed with RCA Records in 1965, he battled with label executives over the polished 'Nashville sound' that was used in several recording sessions. Jennings didn’t want the lush orchestration and background choruses on his songs. The musical outlaw wanted to play his music his way, choosing his own songs and arrangements and using his own band. Waylon’s basic live-sounding production earned him many hits, including ‘I’m a Ramblin’ Man.’

  • 3

    'I've Always Been Crazy'

    From ‘I’ve Always Been Crazy’ (1978)

    The album ‘I’ve Always Been Crazy’ produced two major hits for Jennings -- the title track and a song called ‘Don't You Think This Outlaw Bit's Done Got Out of Hand,’ which was Jennings' personal statement on the state of the outlaw movement. Although being an outlaw was more about musical style than behavior, this song was written after Waylon was detained by the Drug Enforcement Administration in 1977 for possession of cocaine and conspiracy to distribute. Jennings was never convicted of the crime, however, due to faults in the legal process. ‘I’ve Always Been Crazy’ is a shoo-in on our list of the Top 10 Waylon Jennings songs.

  • 2

    'Good Ol' Boys' (Theme From 'The Dukes Of Hazzard')

    From ‘Music Man’ (1980)

    Waylon Jennings first served as the narrator for 1975’s 'Moonrunners,' but the movie was later re-worked to create the television series 'The Dukes Of Hazzard.' Jennings was once again tapped to serve as host for the TV series, which premiered on CBS in 1979. In addition to lending his voice to the show, Jennings also wrote the theme song ‘Good Ol’ Boys.’ Released as a single, the tune hit No. 1 on the Billboard Country Singles chart and became his biggest hit on the Billboard Hot 100 pop charts. The record was also certified double-platinum by the Recording Industry Association of America with over 2 million in sales.

  • 1

    'Luckenbach, Texas'

    From 'Ol' Waylon' (1977)

    ‘Luckenbach, Texas’ is a song that many people assume that Waylon Jennings wrote, but it was actually penned by Chips Moman and Bobby Emmonds. Ironically, the tribute about an easy way of life in a small, laidback Texas town was written and recorded by men who had never been to Luckenbach, Texas. Jennings recorded the song anyway, as he liked the overall theme of getting back to the basics of love. The single was also Waylon’s biggest Billboard chart hit, staying at No. 1 for six weeks.