Unintentionally, a number of classic country music fans treat artists as one-dimensional caricatures. It's simple and sometimes satisfactory to sum up Johnny Cash, George Jones, Waylon Jennings, Tammy Wynette and others with one-sided tales of hard living and debauchery ... but hair-raising legends about hell-raisers fall short of defining anyone's life and legacy.

For example, the ornery ol' Waylon Jennings that many associate with that familiar "flying W" logo overshadows the personality of a funny guy and family man responsible for memories independent of his vices or outlaw affiliation. Don't believe it? Read on for five quick examples of how Jennings' sense of humor shined onstage, in the studio and through television and film appearances.

  • "It Don't Matter Who's in Austin ..."

    Although there’s differing accounts as to what drew his ire, Jennings freely admitted over the years that he wrote “Bob Wills Is Still the King” as at least a partial slight to his longtime friend Willie Nelson. During the 1989 show that became the Live in Austin, TX DVD and CD, Jennings says as much while poking fun at himself.

    “I really wrote that song because I was mad at Willie, and it was a letter,” Jennings says. “I thought I’d write him a letter in rhyme. The more I got along with it, I thought, ‘Hmmm, this ain’t bad. Willie’s going to really like this. He’s going to wish he had one like that.’ Sure enough, he got four or five of them.”

  • "Follow That Bird"

    Jennings wasn’t the only country legend to interact with the creations of Jim Henson. Rowlf the dog debuted on The Jimmy Dean Show, Glen Campbell cut a duet with Oscar the Grouch, and Roger Miller hosted one of the more memorable episodes of The Muppet Show. Yet, considering Jennings’ gruff exterior and outlaw image, there’s something surreal about his on-screen chemistry with Big Bird.

  • "Pinball Wizard"

    Jennings famously shunned Music Row to hang out at fellow renegade Tompall Glaser's studio, Hillbilly Central. The fast friendships formed there between Jennings and the Glaser Brothers’ inner circle had as much to do with the pinball battles at the nearby Burger Boy Drive-In as any sort of clandestine attempt to change the music industry.

  • "What Do You Think, Waylon?"

    TNN personality Gary Chapman hosts this loose audience Q&A, during which Jennings has fun talking politics (“You really don’t want me to run for office. I don’t even want to walk anymore. I have a hard enough time with that”) and the rise of popular artists with image consultants (“Can you imagine me and Willie Nelson in a room with image consultants?”).

  • "Yabba Dabba Doo!"

    The footage of the Highwaymen performing “The King Is Gone (So Are You)” at Farm Aid 1992 basically shows old buddies laughing at a tried-and-true inside joke. Jennings almost cracks up over one of his lines in this song about a drunken, lonely night, popularized a few years earlier by George Jones.