Alan Jackson scored one of the biggest hits of his entire career when he recorded “It’s Five O’Clock Somewhere” with Jimmy Buffett in 2003, but he was not the artist the songwriters had in mind when they wrote the song.

In fact, the song didn’t come to him until several other artists had passed on it!

Jim “Moose” Brown and Don Rollins co-wrote “It’s Five O’Clock Somewhere,” and Rollins tells the Boot that their original demo was “very island-ly,” framed by acoustic guitars and punctuated by steel drums. “It was definitely that ‘Margaritaville’ feel.”

The song was inspired by an old phrase Rollins used to hear from a colleague when he was a band teacher, and Brown signed on immediately when he floated the idea. They wrote the song quickly, Rollins recalls, and the name-check of Jimmy Buffett was there from the beginning, long before Buffett became involved in the recording.

“It was me being sarcastic, poking a little fun at the ‘What would Jesus do?’ bumper stickers,” Rollins relates. “It happened to be exactly the right thing for that situation. That was the way they brought Buffett into the song, it turned out to be the thing to make the song work for that situation.”

Brown and Rollins had intended the song for a newly signed artist named Colt Prather. Brown was playing piano on an album he was cutting for Sony at the time, and the label had specifically requested beach-y material with a Buffett vibe, but they passed on “It’s Five O’Clock Somewhere” immediately after it was completed and pitched.

Country beach king Kenny Chesney also passed on the song.

“I think they wanted to not do so much beachy stuff anymore,” Brown revealed in an interview in 2010. “If we had gotten it to him three years earlier, he probably would have jumped on it, but the timing wasn’t right.”

When the songwriters got the news that Jackson had placed the song on hold, they were initially surprised.

“The idea that someone as country as Alan Jackson might be interested in that song never even occurred to me,” Rollins admits. “Then I got wind that he was wanting to do a duet with Buffett, and it made a little bit more sense at that point.”

Released on June 2, 2003, “It’s Five O’Clock Somewhere” ended up topping Billboard‘s Hot Country Songs chart for eight total weeks, beginning on Aug. 9, 2003. It also crossed over to the mainstream Hot 100, where it peaked at No. 17. The song went on to win a CMA Award for Vocal Event of the Year.

Sterling Whitaker is a Senior Writer and Senior Editor for Taste of Country. He focuses on celebrity real estate, as well as coverage of Yellowstone and related shows like 1883 and 1923. He’s interviewed cast members including Cole Hauser, Kelly Reilly, Sam Elliott and Harrison Ford, and Whitaker is also known for his in-depth interviews with country legends including Don Henley, Rodney Crowell, Trace Adkins, Ronnie Milsap, Ricky Skaggs and more.