Jimmy Buffett, 1946-2023
This past weekend’s death of Jimmy Buffett is a musical loss that cuts deep with me. The legendary leader of the Parrot Heads was a constant fixture on my parents’ playlists growing up. I have so many fond, early childhood memories of hearing his music blaring through our backyard speakers. As a result, he was one of the first artists with whom’s catalog I became very familiar with, particularly that magical period of 70s LPs which ranged from 1973’s A White Sport Coat and a Pink Crustacean to 1979’s Volcano. As I grew into adulthood, Buffett remained a favorite of mine, thanks both to his mid-2000s resurgence on country radio, as well as a new summer tradition that found my friends and I making the trip to the Alpine Valley Music Theatre in East Troy, Wisconsin. There we would see him and The Coral Reefer Band live in concert, as well as partake in the cult-like festivities that could only be delivered by his legendary Parrot Head fanbase. I eventually saw the man in concert a grand total of ten(!) times, a total that surely no other artist will ever match in my lifetime.
The spirit of Buffett’s music was an undeniably unique and special one, both in his formative country-rock performances, as well as his iconic tropical and reggae-leaning anthems, a fusion that would come to be known as “Gulf & Western”, and a sound that would often be imitated, but most certainly never duplicated. His music exuded joy, fun, love, and positivity, all of which will live on forever in the memories left behind with his records. As he once espoused, “It takes no more time to see the good side of life than it takes to see the bad.” We could all afford to greater prescribe to Jimmy Buffett’s views of life and the world around us.
I’ve been planning for sometime now to start a new feature that ranks and counts down my personal favorite songs in the catalogs of my favorite artists; I was merely debating on which artist to begin with. As I played Jimmy Buffett’s music in memory of him over this Labor Day weekend, that choice became very clear.
So, here are my twenty-five favorite songs from the canon of Jimmy Buffett. Rest easy Jimmy, and thank you for the memories and the music!
25) “Fins” (1979)
A joyous live staple and an undeniable highlight in every Jimmy Buffett concert. Drivers, be alert if you encounter a Parrot Head on the freeway, and keep your distance if you do. If the chorus of “Fins” comes on the car stereo, there is simply no choice but to remove your hands from the wheel and perform the concert choreography that became synonymous with this track throughout the years.
24) “Miss You So Badly” (1977)
A popular deep cut from Buffett’s biggest-selling album, “Miss You So Badly” is a tender mid-tempo that perfectly represents the Gulf & Western monicker, with his warm vocals sounding tremendous against the then-unique combination of twangy guitar and tropical keys.
23) “Mexico” (1995)
I honestly knew this as Jimmy Buffett song long before I learned it was a James Taylor original. I love both versions today, but will always be biased to Buffett’s. Thematically, it was obviously a perfect cover selection, and Buffett does Taylor’s original proud while adding his own unique charisma and character to the proceedings. It puts an instant smile on my face and an extra pep in my step.
22) “Cheeseburger In Paradise” (1978)
Outside of “Margaritaville” of course, perhaps no other track today represents the cult-fever and actual brand that eventually came to be associated with Jimmy Buffett than this ridiculously fun novelty. Upon its initial release however, “Cheeseburger In Paradise” was merely another encapsulation of Buffett’s goofball, real-life personality. And it remains that above anything else today as well. When he starts belting “I like mine with lettuce and tomata..”, I dare you not to sing along and enjoy every God-loving moment of it.
21) “Making Music for Money” (1974)
One of the first things I did upon hearing of Buffett’s death on Saturday was pull out my vinyl copy of A1A and turn it up loud. As I listened to the lyrics of this crunchy opening track, I couldn’t help but grin ear-to-ear as I thought about the unconventional manner in which he became a lucrative rock star. He did so with very little industry support, but rather by staying true to his musical identity and by finding his own manner of connecting with an audience that ultimately paid him back in droves. Not just in terms of millions of dollars, but with the same kind of musically inspired joy that he sings of here.
20) “Bama Breeze” (2006)
A late-career gem that pays proud tribute to the humble but spirited ocean-side bars that were ravaged by the wrath of Hurricane Katrina a year earlier. His voice sounds just as full and comforting as it did on his prime recordings three decades prior.
19) “Life Is Just A Tire Swing” (1974)
A charming, blue-collar anthem that cheerfully celebrates an upbringing that was short on cash, but long on music, dreams, and love, and ultimately resulted in a rags-to-riches conclusion. Regardless, it never loses sight of the fact that life is an ever-changing pendulum, and that even the most prestigious ones have their peaks and valleys.
18) “Knees of My Heart” (1984)
I still have vivid memories of this infectious island chorus bouncing around in my brain as a young child. I hear it again now and I’m quickly transported back to that time. And Jimmy Buffett’s music makes me just as happy now as it did then.
17) “Something So Feminine About A Mandolin” (1976)
I have very little doubt that the origins of my affinity for acoustic country instruments can be traced back to this beautiful chestnut from Havana Daydreamin’. It’s one of his most sensitive and understated performances, and the marriage of his voice and the instrumentation here is positively sublime.
16) “Trip Around the Sun” (featuring Martina McBride) (2004)
It was an ironic twist of fate in the early-to-mid-2000s when Jimmy Buffett was suddenly getting the recognition that Nashville long denied him for being the quality country music singer and genre influencer that he always truly was. His 2004 proper country album, License to Chill, was filled with plenty of raucous tracks and collaborations, but my favorite moment was this beautiful duet with the Music City “it-girl” of the time, Martina McBride. It’s a beautifully reflective and nostalgic song, and their voices prove to be a perfect, unexpected match.
15) “Ringling, Ringling” (1974)
There’s such a sad story of loss lingering underneath the peppy country-rock trappings of “Ringling, Ringling”, with its vivid imagery of a small town that is on its last legs. Nevertheless, Buffett’s performance jangles with the kind of pride and cherished memories that you know are still present on those streets. “Ringlin’, Ringlin’ you’re just slippin’ away/I wonder how many people will be there a year from today/Cause the streets are dusty and the bank has been torn down/It’s a dyin’ little town.” Classic storytelling was definitely a Buffett strong suit.
14) “One Particular Harbour” (1983)
In terms of his pure, unadulterated island tracks, “One Particular Harbour” is arguably his ultimate cornerstone. The sound and spirit of the tropics, as well as Buffett’s all-encompassing fascination with them, are all just captured here so seamlessly well. I love how everything builds so marvelously to the final, climactic chorus.
13) “Changes In Latitudes, Changes In Attitudes” (1977)
“If we couldn’t laugh, we would all go insane.” That one line perfectly sums up the Jimmy Buffett mantra in one fell swoop, while the song itself serves as the endlessly infectious anchor to the biggest album of his career. It’s the epitome of escapist music, while still maintaining the realism of everyday life at the core.
12) “Brown Eyed Girl” (1983)
It’s impossible to ever match the magical energy of the Van Morrison original, but damn did Buffett do a hell of a job reinventing the 1967 classic into something that was both reverent of its predecessor, and wholly his own vision. The uproarious amps at the beginning and how they emphatically segue into the steel drum solos works so well in hooking the listener into an inescapable musical joyride.
11) “Margaritaville” (1977)
Sure, many Parrot Heads have developed a slightly contentious love-hate relationship with “Margaritaville” over the years. But that’s merely over the fact that so many in the general public erroneously think that it was the one-dimensional extent of Jimmy Buffett’s music. It’s a relationship that die-hard followers of many artists have with said artist’s signature song. But there’s still a reason “Margaritaville” is the signature song. It’s that universal moment where a wide audience finally caught onto the unique appeal of his work. And, it remains a flawlessly clever and colorful record, as well as a quality depiction of what made Buffett such a skilled narrator for the life experience of everyday people.
10) “It’s Five O’Clock Somewhere” (with Alan Jackson) (2003)
By the time Alan Jackson and Jimmy Buffett’s mega-collaboration held the country charts hostage for two solid months in the summer of 2003, Buffett’s influences had already been at the forefront of the Nashville mainstream for sometime, with acts like Kenny Chesney and later Zac Brown Band fostering a beach-country subgenre that would stay prominent for much of the decade. But it was a valiant traditionalist like Jackson, at this point an unflappable country God on the levels of Merle Haggard and George Strait, who vaulted Jimmy back into the cultural consciousness, not only because he was a huge fan, but also because of his awareness of Buffett’s influence on modern honky-tonkers like himself. Like all of the songs on this list, “Five O’Clock” never gets old, even after a billion listens. Their chemistry is off the charts, and the moment when Buffett finally arrives on the final chorus marks one of the most jubilant musical moments of all time.
9) “Why Don’t We Get Drunk” (1973)
This stone country classic is still making listeners both laugh and blush endlessly a half-century later, and it truly remains the gold standard for songs of its ilk. There’s a long list of country bros, rock wannabes, and Hip Hop posers alike who wish they could pen a sex jam with even the ounce of wit, style, or even bravado that this one has. And, on a side note, this song had to have accounted for a considerable amount of waterbed sales back in the day, right? Wow, remember those?
8) “Son of a Son of a Sailor” (1978)
An epic, winding, nautical narrative that provides a fascinating display of Buffett’s classic and imaginative storytelling style, not to mention creative wordplay. It was also penned in tribute to Buffett’s grandfather, a steamship captain who was a monumental influence throughout his life. You can definitely hear the pride and personal meaning behind the song in every moment of his reverent vocal performance. A true signature moment in his discography.
7) “Come Monday” (1974)
His initial taste with any level of radio success, “Come Monday” is also inarguably the quintessential love song in Jimmy Buffett’s storied catalog. His yearning vocal is so powerful against the wistful, lonely arrangements. He’s criminally overlooked when the country-rock movement of this era is assessed; this performance is just as lovely (if not more) as any ballad that The Eagles sent soaring up the charts throughout the 70s.
6) “Brand New Country Star” (1974)
A hilarious and all-too-accurate account (even by today’s standards) of an aspiring music star’s struggles to break through to the big time. It’s delivered with the plum-perfect combination of earnestness and sarcasm, with a comical, self-deprecating narrative that is unwavering throughout. When Buffett wails that final delivery of “I mean, he can either go country or pop” and then proceeds to close the song with an over-exaggerated yodel? Fantastic.
5) “The Wino & I Know” (1974)
Man, what a hook the title phrase of this track proves to be. “The Wino & I Know” is easily one of Jimmy’s most durable and utterly infectious cuts. It’s perfectly executed pop contagion filtered through a scrappy country-rock lens. I was singing this one loudly before I knew even half about what it’s really about. Now that I can follow the quirky journeyman storyline more thoroughly, it certainly enhances the listening experience. But if I’m being 100% honest, I still love the song most just for the ridiculous range of the vocabulary (Milkshakes in motion, donuts too hot to touch, 78s by Hank Snow, Pickup trucks rustin’) that still makes it so irresistible to sing along to decades later.
4) “Pencil Thin Mustache” (1974)
At this point in the countdown, you’re probably picking up on just how prominent an album Living and Dying in ¾ Time was in our household. It most definitely reached life-soundtrack level status, thanks to entertaining cuts like “Pencil Thin Mustache”, a tongue-in-cheek observation as to society views the retro glories of the past with such rose-colored idealism. Similar to “The Wino & I Know”, this was just a flat-out fun song to sing along to, thanks to the wildly fun lyrical imagery, which of course only became more amusing and relatable with additional life experience and wisdom. This is musical camp of the highest order. “Yeah, Brylcreem, a little dab’ll do ya….”
3) “Woman Goin’ Crazy On Caroline Street” (1976)
Now, here’s a song that we sang along to in our youth, with no earthly idea of what was being referenced. In fact, there’s a funny story of a neighborhood friend once expressing concern to my parents that my pre-school-aged sister was frequently belting the chorus to this portrait of a prostitute and her down-trodden patrons. This only makes me belt it louder when I hear it today. Eye-brow raising storyline and personal story aside, I really do regard “Caroline” as one of Buffett’s definitive moments on record. His vocal presents the woman’s story almost with a regal poise, a layered texture and narrative that nods to the backstory that surely led her to this point in life. The production meanwhile hits such a sweet spot that perfectly blends elements of honky tonk, countrypolitan, and rock & roll.
2) “Tin Cup Chalice” (1974)
“Tin Cup Chalice” has actually been a late-blooming favorite of mine. I was always aware of it and enjoyed it, but it wasn’t really on my adult radar until it was snuck into the playlist of the final Alpine Valley show my friends and I attended in 2022. It just struck me in one of those special live music moments, and I’ve listened to it frequently since. I just love the melodic structure and pacing of the entire track. It hypnotizes me, and by the time he gets to the passionate deliveries of lines like “I wanna go back down and die beside the sea there” or “Fill it up! With red wine!”, I’m completely consumed by the song. Those moments certainly hit me in a completely new way over the past few days.
1) A Pirate Looks At Forty (1975)
This is another classic that has become more meaningful for me with the passage of time, and the fact that the age referenced in the title is suddenly knocking at my own door. It’s a gracefully reflective performance that grapples with so many monumental life considerations: past mistakes, squandered potential, where we fit in the world, and how all of that impacts us as life continues to pass by. The lyrical narratives may be specifically referencing the classic rambling musician’s lifestyle, but they’re delivered in such a universal way that can resonate with all of us and our own personal journeys. It truly is the ultimate classic in Jimmy Buffett’s canon, and emblematic about why his music was so important to so many. He was able to musically parlay his own unique experiences, character traits, and passions in a unique and rare manner that was true and personal to him, but also tapped into our own personal life stories. Many times, he did so by allowing us to escape whatever life had challenged us with, and other times, he tackled them with us head-on. It’s a special gift that only few artists truly possess and realize, and that’s why it impacts us so profoundly when those artists are suddenly no longer among us.
The 706 
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