“At a moment like this, I can’t help but wonder … What would Jimmy Buffett do?,” Alan Jackson ponders in his and Buffett’s 2003 smash “It’s Five O’Clock Somewhere.” Buffett then joins in to offer his sage advice, and Jackson’s handoff reflects the revered status to which Buffett rose in music and pop culture overall.

As previously reported, Buffett died on Friday (Sept. 1) at age 76. As announced on his website and social media accounts, “Jimmy passed away on the night of September 1st surrounded by his family, friends, music and dogs,” the early Saturday morning (Sept. 2) post reads. “He lived his life like a Song till the very last breath and will be missed beyond measure by so many.”

Buffett became a force on Billboard’s charts over six decades — after working as a correspondent for Billboard magazine. He made his chart debut just over 50 years ago, when “The Great Filling Station Holdup” entered the Hot Country Songs chart dated May 12, 1973. Later that year, he reached the Top Country Albums and Adult Contemporary charts for the first time, and in 1974 he made his way to the Billboard Hot 100, as “Come Monday” marked his first entry, and first top 40 hit, climbing to No. 30.

Buffett charted 13 Hot 100 hits during his lifetime, through 2011. After tallying five top 40 entries in the ’70s, reaching the top 10 with his signature anthem “Margaritaville” (No. 8, 1977), he tallied his second- and third-biggest hits thanks to turns on Jackson’s “It’s Five O’Clock Somewhere” (No. 17, 2003) and Zac Brown Band’s “Knee Deep” (No. 18, 2011). The latter two tracks also became Jackson’s first and second No. 1s on Hot Country Songs, where Buffett logged 20 hits, including eight top 40 titles.

The Pascagoula, Miss., native, raised in Mobile, Ala., also sent 40 albums onto the Billboard 200 chart during his lifetime, including 12 top 10s, from Son of a Son of a Sailor (No. 10, 1978) through Life on the Flip Side (No. 2, 2020). He led the list with License to Chill in 2004. He charted eight top 10 sets on Top Country Albums, led by three No. 1s: License to Chill, Take the Weather With You (2006) and Life on the Flip Side.

Meanwhile, Buffett became the rare Billboard alum to segue from the edit department to the chart well. He resigned as a Nashville reporter when his first album was released in 1970. As he explained in 2020, “There was a conflict of interest. When I signed to Barnaby (Records), I couldn’t still write for Billboard, so that was the end of my days there.” (Of his assignments at Billboard, he said in 2021, “I can never give anybody a bad review because I knew how hard it was to get up there.”)

“But I’m glad I got 50 years of albums in me,” he mused in 2020. “This thing’s been an absolute joy. We’ve figured out ways to keep it going. I think it’s really about learning to be a performer before anything else and always trying to better yourself on stage. That’s the key, that core experience, and what’s kept me going. It’s been a good run.”

Below, spotlighting Buffett’s beloved catalog, are his 10 biggest hits on the Hot 100, ranked from No. 10 to No. 1. (The recap is based on actual performance on the weekly Hot 100 chart. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least. To ensure equitable representation of the biggest hits from each era, certain time frames were weighted to account for the difference between turnover rates from those years.)