Set Sail with a Pirate's Playlist - Episode 1 Quiz

Answer: A White Sport Coat and a Pink Crustacean

Live In Concert: 900+

This track is a foundational staple of the live catalog. It's a member of "The Big 8", the eight songs that 'must be played' at live shows. "He Went to Paris" was always a touching focal point of every live show. Jimmy was inspired to write it after spending time on Chicago's North Side with a one-armed Spanish Civil War veteran named Eddie Balchowsky. He worked as a cleanup guy at the Quiet Knight folk club in the city's Lakeview neighborhood.

Answer: A White Sport Coat and a Pink Crustacean

Live In Concert: 900+

This classic is an undisputed highlight of a Jimmy Buffett concert. The song consistently turns twenty thousand Parrotheads into an alternate universe version of the Mormon Tabernacle Choir. On his landmark live album, "Feeding Frenzy", he playfully cues only the women in the audience to blast out the chorus by calling for the "all girls choir from Lima, Ohio." It is the ultimate excuse for the crowd to cut loose, especially when Jimmy wraps up the joke by calling for the men to join back in for the finale.

Answer: A White Sport Coat and a Pink Crustacean

Live In Concert: The Early Tour Era

This early storytelling track is a vintage deep cut from Jimmy's live catalog. While modern databases only document a handful of live performances (50+), the song was his very first track to ever hit a Billboard chart, climbing into the Hot Country Singles chart in 1973. It is also the track that brought harmonica player Greg "Fingers" Taylor into the fold. They first jammed when Fingers casually walked up to join Jimmy while he was busking on the student union steps at Southern Miss. This historic meeting has been enshrined with a permanent bronze plaque right outside the building, stating simply, "Where Jimmy met Fingers".

Answer: A White Sport Coat and a Pink Crustacean

Live In Concert: 500+


This classic represents the fun, quirky side of Jimmy's early catalog, climbing to number 23 on the Billboard Easy Listening chart back in 1973. On his first live album, "You Had to Be There", Jimmy tells the story, "We used to go down to the Islander Drive-In on Boca Chica Key and make Purple Passion." Spoiler 1: Purple Passion was a potent party drink, not just grape juice. Hence, the ultimate need for a grapefruit and juicy fruit hangover cure. Spoiler 2: The Islander Drive-In wasn't actually on Boca Chica Key. It was a little bit further down the road on Stock Island, right next to Key West.

Answer: Living and Dying in 3/4 Time

Live In Concert: 400+

This may have been the single most anticipated song I ever had at a Buffett concert. I started going to shows in 1988 during the "Hot Water" tour. This was in the midst of a lawsuit over "God's Own Drunk." The son of the original performer alleged that Jimmy stole the monologue from the late 1950s hipster comedian Lord Richard Buckley. In true Parrothead fashion, Jimmy answered the injunction by taking the song off the list and replacing it with a hilarious diss track called "The Lawyer and the [word I can't use in a quiz]". When he finally brought the classic back years later, he simply told the crowd, "Y'all want to hear it; I want to sing it. Let 'em sue."

Answer: Living and Dying in 3/4 Time

Live In Concert: Early Tour Era

Jimmy Buffett has written ballads, anthems, folktales, and just about any other kind of song you can think of. "The Wino and I Know" is what I would call a great little "ditty." Being part of the group of early album cuts, it rarely made the summer tours, and is documented only a very few times (30+). For the lucky fans who caught those rare performances, classic lines like, "the wino and I know the joys of the ocean / like a boy knows the joy of his milkshake in motion" are Parrothead gold.

Answer: Living and Dying in 3/4 Time

Live in Concert: 700+

Jimmy's love of old Hollywood was front and center on "Pencil Thin Mustache". The track is packed with nostalgia for vintage pop culture. It name-drops classic characters like Boston Blackie, Ricky Ricardo, and the Sheik of Araby. As the years rolled on, Jimmy would pause his shows to educate younger Parrotheads on who they actually were. He would channel Desi Arnaz, telling the crowd, "I've got some 'splainin' to do!" Jimmy later admitted the song originally started with a simple obsession over a two-toned Ricky Ricardo jacket, laughing that the older he got, the more 'splainin' he had to do.

Answer: Living and Dying in 3/4 Time

Live in Concert: 1,200+

This legendary ballad stands as an absolute heavyweight of a live Buffett concert, a founding member of "The Big 8. Jimmy wrote the masterpiece in 1973 at a Howard Johnson's hotel in Mill Valley, California while missing his future wife, Jane Slagsvol. When playing it live, he would routinely switch up the studio lyrics to match his current location. "I just can't wait to see you again" became "It's so nice to be in Boston/Denver/Fire Island again" or whichever venue he was playing that night.

Answer: A1A

Live In Concert: The Early Tour Era

This is one of many great storytelling songs that do not appear often in modern databases of live shows (40+). One of the best things about this track is that it has a line calling back the title of a previous album, "Living and Dying in Three-Quarter Time."

Jimmy wrote this song as a shout-out to a real, funky square-dancing crew called the Nautical Wheelers. They would do their thing and spin around under a parachute canopy at Old City Hall in Key West. It has always felt like a campfire song when all the kids have gone to sleep and it is just Mom and Dad giggling about the way the kids acted during the day.

Answer: A1A

Live In Concert: The Early Tour Era

This is another one of many great storytelling songs that does not appear often in modern databases of live shows (100+). If you were ever lucky enough to hear this one live, you caught some far off lightning in a bottle. One of the best nuggets about this track is that it was the very first song Jimmy wrote when he originally rolled into Key West. Never one for pretension, the lyric "Yeah with a tin cup for a chalice, fill it up with red wine / And I'll be chewin' on a honeysuckle vine" is quintessentially Parrothead.

Answer: A1A

Live In Concert: The Early Tour Era

This track represents a rare treat for deep-cut collectors tracking his live shows (80+). "Migration" perfectly captures the Gulf & Western style that Jimmy invented. The lyrics spell it out clearly: "I've got a Caribbean soul I can barely control / and some Texas hidden here in my heart." It gives us a beautiful look at his early days on the road before the Margaritaville empire took over.

Answer: A1A

Live In Concert: 1200+

Whether played with the full Coral Reefers band or just Jimmy and his acoustic guitar, "A Pirate Looks at Forty" remains a masterpiece of storytelling. Jimmy wrote the track as a nod to his real-world buddy Phillip Clark, a modern-day drug smuggler looking back on his life right at the Chart Room bar in Key West.

Phil was a charismatic, twentieth-century pirate who heavily influenced Jimmy's early island style with his legendary tall tales. When he later got into major trouble with the law and had to flee the island, locals jokingly began calling Jimmy's classic track "A Pirate Looks at Five to Ten".

Answer: Havana Daydreamin'

Live In Concert: Early Tour Era

"Something So Feminine About a Mandolin" supplies the quiet counterpart to the rowdy road story of "Kick It in Second Wind". Jimmy co-wrote both tunes with his future wife, Jane Slagsvol. He penned the lyric "The lady she played so easy and fine" after watching her pick her mandolin in an Austin pasture under the stars. Modern databases only track a grand total of two (2) acoustic live performances, over two decades apart, for this deep cut. The ballad is a tribute to Jane, capturing the early days of their relationship before they officially tied the knot.

Answer: Havana Daydreamin'

Live In Concert: Early Tour Era

"Woman Goin' Crazy on Caroline Street" captures the wild paradise of Key West in the mid-1970s. Co-written with folk legend Steve Goodman, the track feels like a local legend. Yet, it was rare for concerts (110+). The song's mystique comes from the real-life character who inspired it. The "woman" wasn't a woman at all, but a local guy who would dress in drag, flash his shaved legs, and shock tourists outside the bars. If you are one of the lucky few who caught this deep cut live, the next margarita is on me.

Answer: Havana Daydreamin'

Live In Concert: Early Tour Era

This track is a tribute to Jimmy's grandfather, Captain James Delaney Buffett. The sailor provided the nautical legacy that shaped Jimmy's entire life. While the song evolved into a live rarity over the decades (180+), it held a foundational place in his early acoustic sets. In a Nashville standoff during his early songwriting days, a record producer demanded that Jimmy change the ending of the song to let the old man live. Jimmy flatly refused to alter the truth, stated simply, "Because he did," and walked out. It remains unique as the very first track Jimmy ever re-recorded for a later project, giving the song a second official release on this album.

Answer: Havana Daydreamin'

Live In Concert: 300+

Jimmy openly credited the real-life inspiration for "Havana Daydreamin'" to Peter Matthiessen's 1975 novel "Far Tortuga". He fell in love with the book's vivid descriptions of Caribbean turtle crews (you don't want to know) to invent his own fictional getaway. In a crazy piece of production history, the entire album was originally supposed to be named after the rowdy track "Kick It in Second Wind". ABC/Dunhill executives thought the original lineup was too raunchy for '70s radio, forcing him to change the title and drop specific songs. Even with all of this turmoil, executives failed to catch tracks like "My Head Hurts, My Feet Stink, and I Don't Love Jesus" or his tribute to a drag queen, "Woman Goin' Crazy on Caroline Street".