Toby Keith videos are some of the most entertaining clips in country music. The singer-songwriter has built one of the biggest careers in the genre, and his unusually clever videos have contributed much to that success.

Though almost every major country artist releases videos for their singles, few of them have come anywhere close to matching the pure entertainment value of Keith's clips, which are like miniature films. The fact that the superstar can laugh at himself in his videos makes them that much more appealing. But he also has a more serious side, as at least one of the following music videos demonstrates.

Our list of the Top 5 Toby Keith Videos is sure to bring a smile to your face.

  • 5

    "Red Solo Cup"

    Keith's video for "Red Solo Cup" has an all-star guest list, featuring appearances by Jeff Dunham, Carrot Top, Ted Nugent, Sammy Hagar, Craig Ferguson, Eric Church and more. The hugely entertaining clip had passed more than 600,000 views on YouTube before the album it's on, Clancy's Tavern, was even released, and has since amassed more than 30 million views online. "Red Solo Cup" won Music Video of the Year at the 2012 CMA Awards.

  • 4

    "My List"

    Keith's video for "My List" was released shortly after the 9/11 attacks on the World Trade Center. The video opens with a couple watching the footage of the attack on the news, then goes on to reveal that the husband is a fireman. The clip perfectly captures the theme of the song, which talks about a man who is trying to slow down and start participating more in the simple joys of life, especially prioritizing time with his family.

  • 3

    "How Do You Like Me Now?!"

    Keith filmed the ultimate underdog revenge fantasy with "How Do You Like Me Now?!" The video depicts the singer as a country star, returning to show the cheerleader who spurned him in high school just what she's missing out on now that he's become ultra-successful. Filmed on a football field, the now-classic clip ends with Keith departing the field in a white stretch limo after reading the former valedictorian the musical riot act.

  • 2

    "Who's Your Daddy?"

    Keith demonstrated his penchant for using celebrity cameos to great effect with "Who's Your Daddy?" The clip stars former Playboy Playmate Tiffany Fallon as a an attractive girl who trespasses in a mansion, coveting all that she sees there. Cledus T. Judd also appears, pretending the mansion is his in order to score with the young lady, before it's revealed that he is the lawn man.

  • 1

    "As Good As I Once Was"

    "As Good As I Once Was" is the perfect clip to head up the list of the Top 5 Toby Keith Videos. It's got all the hallmarks of a Keith classic: It takes place at a bar, it features self-deprecating humor, and it ends in an unexpected way that you don't see coming. Throw in some Viagra, one hot (and one not-so-hot) twin, a bar fight and a trip to the hospital, and it's a recipe for a classic clip that's still funny every time you watch it.