Country icon and everyone's favorite rum connoisseur Kenny Chesney has spent half his life in the music industry.

As an up-and-coming singer-songwriter, Chesney begin his career in 1993, at just 25 years old. But now, with two-plus decades in the business behind him, Chesney has recorded more than a dozen studio albums (many which have been certified gold or higher), gone on tour a whole bunch of times (breaking records along the way) and won countless awards (including four CMA Entertainer of the Year trophies and four ACM Entertainer of the Year trophies).

Along the way, Chesney has also participated in some impressive collaborations and duets. Whether on his massively popular duet with Pink, "Setting the World on Fire," or on his deeper cuts (ever heard his cover of the holiday favorite "Pretty Paper" with Willie Nelson?), Chesney has worked with some of the best artists inside and outside of the country genre -- in the studio and onstage!

Below, take a look at some of Chesney's best live collaborations. Taylor Swift and a few other big country names make appearances, but you may be a bit surprised by who else is on the list (one of them isn't even a singer!).

  • Kid Rock

    Although Rock has never been officially labeled as a country artist, songs such as his 1999 smash "Cowboy" have earned him fans in the genre. So when Chesney made his way to Rock's hometown of Detroit, Mich., during his 2016 Spread the Love Tour, it only made sense to ask Rock to join him onstage for a rousing rendition of "Cowboy." Chesney called Rock his "brother in music [and] in life," and the two clearly loved sharing the stage, often high-fiving each other as they worked the crowd together.

  • Taylor Swift

    When Chesney kicked off his The Big Revival Tour in 2015, fans knew they would be in for a treat. But considering that Swift had recently announced her first pure-pop album and her move away from country music, no one expected the superstar to show up to sing with Chesney on his 2003 hit "Big Star." They couldn't have picked a better song, though: With lyrics including "So she sings tonight to 20,000 plus and the young girls scream out loud," it's the perfect tune for Swift to sub in on!

  • Dave Matthews

    Chesney and Matthews are certainly not strangers: The two have teamed up more than once, including for their 2008 duet "I'm Alive." But even before that, Matthews became one of Chesney's earliest onstage collaborators when he joined the country singer onstage during a 2007 show in Atlanta, Ga. Matthews was in town to play a concert of his own when Chesney asked him to hop on stage for a quick duet, which turned into a three-song medley of Matthews' own track "Where Are You Going," Steve Miller's "The Joker" and Bob Marley's "Three Little Birds." Listen to the audio below and check out a short video of Chesney recounting the experience here.

  • Miranda Lambert

    In 2015, Chesney and Lambert were at the top of their touring game: He was on the road with his record-breaking The Big Revival Tour, while she was on the second leg of her Platinum Tour. So when the two teamed up for a live duet of Chesney's 2011 single "You and Tequila," it was pure country magic. In its original form, the song is already a powerful duet, performed by Chesney and Grace Potter, and Lambert made it even more special.

  • Peyton Manning

    This one goes all the way back to 2003 and includes someone who doesn't even record music ... but when that someone is Manning, we'll give him a pass (pun intended). This collaboration began with Chesney's well-known love of football and his first-ever stadium show, at the University of Tennessee's football stadium in Knoxville. In the middle of his tune "Back Where I Come From," Chesney introduced to the teeming crowd a man who needed no introduction (Manning is an alum of the university, after all).

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