On This Day in 2003, Alan Jackson Released an Award-Winning Ode to Day Drinking and Gave a Fellow Legend His First No. 1

On this day (June 2) in 2003, Alan Jackson released “It’s Five O’Clock Somewhere,” a duet with Jimmy Buffett, as the lead single from Greatest Hits Volume II. Later that year, it reached the top of the country chart, where it stayed for eight nonconsecutive weeks, Jackson’s longest-running No. 1. It also reached No. 17 on the Hot 100, giving Jackson his biggest crossover hit. The single was also Buffett’s first No. 1.

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“It’s Five O’Clock Somewhere” wasn’t just a major chart hit for Jackson and Buffett. It also brought them multiple awards. It won Vocal Event of the Year at the CMA Awards, giving Buffett his first CMA win. The hit took home a trophy for the same category at the ACM Awards and Single Record of the Year. Songwriters Jim “Moose” Brown and Don Rollins won the Grammy Award for Best Country Song.

Alan Jackson Almost Didn’t Get to Record This Jimmy Buffett Duet

Alan Jackson wasn’t the first choice to record “It’s Five O’Clock Somewhere.” According to Songfacts, it was originally on hold for Colt Prather, who had just signed a deal with Epic Records.

“We wrote it in February of 2003 and demoed it in March 2003. My publisher took it to the guy who was producing Colt Prather, and he passed on it immediately,” Rollins recalled. A few other artists passed on it as well. Then, Rollins got word that Jackson planned to cut the song.

Rollins thought it was an odd match. “If you hear the demo, it’s very island-y. There are acoustic guitars and steel drum samples, very much Buffett,” he said. “The idea that someone as country as Alan Jackson might be interested in that song never even occurred to me. Then, I caught wind that he was wanting to do a duet with Buffett, and it made a little bit more sense at that point,” he added.

The addition of Buffett to the mix makes the island vibe of the song make sense for Jackson. However, if anyone was the right choice for a song about clocking out early and hanging out at the bar, it’s him. It sits perfectly alongside the long list of his songs like “Summertime Blues” and “Pop a Top” that celebrate hard work and enjoying a few adult beverages.

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