5 of the Best Jimmy Buffett Collaborations

Jimmy Buffett was a steward of a blithe way of life, and as such, amassed a following of like-minded individuals – whether that be his hordes of Parrot Heads or his fellow musicians. Yes, many artists jumped at the chance to perform alongside Buffett throughout his career. From Kenny Chesney to Alan Jackson, find five of Buffett’s best collaborators below.

Videos by American Songwriter

[RELATED: Kenny Chesney Pays Tribute to the Late Jimmy Buffett]

1. “It’s Five O’Clock Somewhere” (with Alan Jackson)

No one has ever touted the merits of finding time to unwind more than Buffett did. “It’s Five O’Clock Somewhere” was more or less a personal mantra, so who better for Jackson to tap for this 2003 duet? Jackson and Buffett’s vocals float overtop a breezy melody, singing about any time being the right time for a cold, strong drink.

2. “Hey Good Lookin'” (with Clint Black, Kenny Chesney, Alan Jackson, Toby Keith, George Strait)

Buffett tapped many big-name country artists for his 2004 cover of Hank Williams’ “Hey Good Lookin’.” The buzzy list of collaborators includes Jackson, Clint Black, Kenny Chesney, Toby Keith, and George Strait. The influence of Buffett’s “island escapism” is felt throughout all of the artists he chose to collaborate with on this cover, making it just as much of a torch pass as it is a tribute to a country icon.

3. “Mack The Knife” (with Frank Sinatra)

On paper, Buffett and Frank Sinatra couldn’t be more different. Sinatra’s sleek New York sensibility stands in stark contrast to Buffett’s barefoot endless summer mindset. Nevertheless, the pair can be heard singing together on the electronically assembled duet, “Mack The Knife.” Buffett cleans up nicely on this track, making his voice sound more austere than ever. It’s a unique choice for Buffett, but it proves that he was more than a one-trick pony.

4. “Too Drunk to Karaoke” (with Toby Keith)

Buffett and Toby Keith joined forces on this playful track in 2013. The pair revel in a drunken stupor in the lyrics, filling up on liquid courage before taking to the karaoke stage. As the song treks on, the pair get a little overserved while waiting for their name to be called. If you keep on drinking you’re gonna be / Too drunk to karaoke, just like me, they sing in the chorus.

5. “Trying to Reason With Hurricane Season” (with Kenny Chesney)

Chesney is just as sun-soaked as Buffett is. Sooner or later, a duet between the pair needed to happen. Luckily in 2018, they united for a rendition of Buffett’s “Trying to Reason With Hurricane Season.” Both artists, who often sing about living on island time, honored the victims of Hurricane Irma in the Bahamas a year prior.

Photo by Rick Diamond/Getty Images for CMT

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