12 Best Jimmy Buffett Songs, Tropical Country Superstar

Born James William Buffett on Christmas Day in Pascagoula, Mississippi, Jimmy Buffett’s early days spent on the water learning to sail deeply influenced his subsequent music career. He first made waves in the 1970s in the country music industry, releasing twangy singles with a down home feel. But when he found his true voice and pioneered both the “Gulf and Western” and “Trop Rock” subgenre movements, he reached international stardom.

Backed by his loyal “parrothead” fanbase, his singles are some of music’s most influential recordings, and even garner “song of the century” status by music critics. With a music brand so powerful it launched a series of successful restaurant chains and other businesses for the entrepreneur, we dive into Buffett’s best songs below.

12. Down at the Lah De Dah

The island time expert and parrothead leader tells listeners exactly where they need to go to wash their troubles away, and that place can be found ‘Down at the Lah De Dah.’ The “Lah De Dah” in the song’s hook is a symbolic stand-in for your favorite watering hole, and it’s no secret Buffett himself has several. A later single release, his Coral Reefer Band sounds crisp and tight in the recording. And the tried-and-true lighthearted message and easygoing vocals highlight the fact that Jimmy’s pioneering “Gulf and Western” country brand has serious longevity.

11. Volcano

This late 1970s number one hit in Canada sounds fun and pleasantly tropical, but its lyrics deal with a far more serious matter. When Buffett headed to a remote Caribbean island to record his latest album in 1979, little did he and his band know that a huge local volcano was on the verge of erupting near the studio they booked. Ever the adventurous type, despite his worries Buffett proceeded with the project, the whole time watching out the studio windows at the smoking timebomb. When his guitarist started playing a rhythmic groove, he chimed in with some lyrics about all the places he didn’t want to go should the volcano erupt. Thankfully, it waited until the mid. ‘90s to blow, long after the release of the album landed him a coveted Rolling Stone feature.

10. Woman Goin’ Crazy on Caroline Street

As his artistry grew, Jimmy enjoyed recording in more tropical locations when he had the chance. However, for his album Havana Daydreamin’, he recorded in the neighboring Nashville town of Murfreesboro. The Tennessee hills and close proximity to country music’s mecca had an impact on the album. Before releasing it to audiences, Buffett actually scrapped a good portion of the track listing, and replaced it with more pure, classic country-sounding cuts. One of those was ‘Woman Goin’ Crazy on Caroline Street,’ a nostalgic, semi-melancholy tune about a lonely, tipsy woman looking for love. His laidback, coastal country sound was a hit. When the album was released in ‘76, it became his most successful record he debuted up to that point.

9. Trying to Reason with Hurricane Season ft. Kenny Chesney

After Buffett set the country music world ablaze with his pioneering trop rock sound, it was only a matter of time before a new generation of musicians came along ready and willing to carry on his (tiki) torch. Though country music star Kenny Chesney’s early hits are country through and through, his image soon turned quite tropical with hits like ‘No Shoes, No Shirt, No Problems.’ For his album Songs for the Saints, he paired up with Buffett for a brand new rendition of the trailblazer’s 1974 tune ‘Trying to Reason with Hurricane Season.’ The pair’s voices blend together effortlessly, and the duet is a great, updated addition to both the island-tinged musicians’ repertoires.

8. Why Don’t We Get Drunk

Part comedy, part social commentary, Buffett was admittedly in a strange place when he wrote the surprisingly twangy, early fan-favorite ‘Why Don’t We Get Drunk.’ An early ‘70s release, the tune was a part of Jimmy’s career before he was established as one of the music industry’s most in-demand performers. His loyal fan club, The Parrotheads, were gaining ground, but he still couldn’t get Nashville execs to give his music the time of day. Annoyed with the simplistic, raunchy country hits coming out of the music city at the time, he wrote this infamous single. The satirical tune not only pokes fun at the country music establishment, but highlights his frustration as an innovative singer-songwriter.

7. Knee Deep ft. Zac Brown Band

Another country artist influenced by Jimmy Buffett’s pioneering work is singer-songwriter and band leader Zac Brown. Not only did Buffett’s coastal country sound influence his work, but reggae legends like Bob Marley did as well, giving Brown’s later country work a more sun-soaked feel. For the fun smash hit single ‘Knee Deep,’ Zac Brown Band teams up with Mr. Parrotthead himself (one of a few collaborations, by the way). The two sing about a tropical vacation getaway they intend to make permanent due to recent breakups. Luckily the remedy is just a boat ride away.

6. Cheeseburger In Paradise

Even those who aren’t true blue Jimmy Buffett fans know at least a few words to his iconic, lasting single ‘Cheeseburger in Paradise.’ The tune is featured on his popular album Son of a Son of a Sailor, and helped launch him to superstardom (and even launched a namesake restaurant chain for many years). The zany tune is based on a true story, which involved Buffett and a fellow sailor getting all but stranded on the water due to a boat mishap. For a few days, they survived on nothing but canned goods and peanut butter. Soon, dreams of juicy cheeseburgers played tricks on his brain and cravings became intense. By the time they reached land, they were starving, and miraculously a new restaurant had just opened up by the dock. And you guessed it, our brave sailor-turned-troubadour ordered a big, juicy burger and thus, penned one of his signature hits.

5. It’s Five O’Clock Somewhere ft. Jimmy Buffett

Country star Alan Jackson ponders an appropriate start time for drinking with buddy Jimmy Buffett for their beloved tune ‘It’s Five O’ Clock Somewhere.’ Released in 2003, despite Buffett’s long career in country music, this hit single marked the first time one of his tunes reached the top spot on Billboard country charts. Their collaboration proved to be especially fruitful when the single also scored a Grammy award for “Best Country Song.”

4. Changes In Latitudes, Changes In Attitudes

Signifying a more “grown up” Buffett in the late ‘70s, ‘Changes in Latitudes, Changes in Attitudes’ added a new layer to his “island escapist” sound. The treasured single found him ruminating over life’s ever-present changes, as opposed to simply searching for the next shabby dock to hitch his boat to. Full of Caribbean-inspired instrumentation that immediately puts you at ease, the single became so popular with his fan base he had to include it in all of his live sets. It’s part of what is known as “The Big 8,” a series of Buffett tunes so beloved by his fans, even after all these years he can’t finish a show without playing them.

3. A Pirate Looks At Forty

“Mother, mother ocean. I have heard your call.” Beautiful lyrics open up one of Buffett’s most memorable singles. Written when he was still in his twenties, despite his extensive sailing background, ‘A Pirate Looks at Forty’ is actually about someone else. Phil Clark was a self-described “pirate” of modern times, and Jimmy met him when the singer-songwriter first moved to the Florida Keys. After Clark’s mysterious death (his body was found on the shores of California during one of his excursions), Buffett decided to write a song in honor of him. With gentle harmonica and plucking guitar, he sings about life spent on the water and the realities of getting older. When Jimmy published his autobiography, he reworked the song’s title and added to the tale, this time documenting his own sea-faring and music-faring journey called A Pirate Looks at Fifty.

2. Margaritaville

Helen of Troy had a face that launched a thousand ships, and Jimmy Buffett wrote a song that launched a thousand restaurant chains. Okay, maybe there haven’t been a thousand, but the beachy troubadour’s Margaritaville restaurants and resorts are scattered among oceanside towns across the globe. Named after one of his biggest hits which boasts the proudly sung line “Wasted away again in Margaritaville” that always gets crowds going, the wildly successful single came to perfectly encapsulate the devil may care island lifestyle his fans love to embrace at his shows. Since its 1977 debut, the pivotal release has not only been inducted into the Grammy Hall of Fame but it has also been recognized by the Recording Industry Association of America as one of the country’s “Songs of the Century.”

1. Come Monday

Before his grand success with his ‘Margaritaville’ single, the yearning, introspective tune ‘Come Monday’ was Buffett’s highest charting track. The title offers an ironic take to those outside of the music industry, who sometimes dread the week day because it means they’ve got to get back to work. For Buffett though, Monday is a slow entertainment industry day, so he looked forward to it because he could spend time with his family he missed so much while on the road. This tune (and the homemade music video) offer an increasingly rare, early look into Jimmy’s rise to fame. Though this single features a technically pre-Parrothead Buffett, it remains to be one of his most enduring hits.

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About Ged Richardson

Ged Richardson is the Founder and Editor-in-Chief of ZingInstruments.com. He has been featured in Entrepreneur, PremierGuitar, Hallmark, Wanderlust, CreativeLive, and other major publications. As an avid music fan, he spends his time researching and writing about new and old music, as well as testing and reviewing music-related products. He's played guitar in various bands, from rock to gypsy jazz. Be sure to check out his YouTube channel, where he geeks out about his favorite bands.

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