Just two nights before he took the stage for 549 people at the sold-out Broadway Playhouse, singer-songwriter Jimmy Buffett was entertaining a crowd 40,000 people larger at Wrigley Field.
Reporter Chris Jones of the Chicago Tribune, which put on the event, led the intimate hour and fifteen-minute conversation on July 17 with the “Cheeseburger in Paradise” singer. The evening discussion covered a wide range of topics including Buffett’s early career, embarrassing anecdotes and his love for Bob Marley. The singer, known for his tropical attire and island-inspired lifestyle, also talked about his entrepreneurial endeavors — stay on the lookout for his retirement homes featuring yoga retreats, paddle boarding and medical marijuana — favorite tiki bars and his new Broadway-bound musical coming to Chicago, “Escape to Margaritaville,” featuring his music and lyrics.
Early in the conversation, Jones brought up Buffett’s large following of Parrot Heads — the name given to his fans — now spanning generations of followers. As for how he’s attracted fans of such a large age range, Buffett said it’s been his ability to remain “authentic and honest” and keep politics off the stage.
“If we didn’t have music, we’d probably be killing each other on a daily basis,” Buffett said.
Following a story from the singer about a 2011 fall he took off a stage in Australia that left him a with a head injury and stitches, the conversation shifted to his most recent project, a musical.
“Escape to Margaritaville” premiered at California’s La Jolla Playhouse in May and will now be traveling to New Orleans and Houston before opening in Chicago at the Oriental Theatre on Nov. 9. Halfway through the night, Tony Award-winning director Christopher Ashley (“Come From Away”) joined the two to discuss his involvement in helping direct and create the show. According to Ashley, “Escape to Margaritaville” follows three different love stories set on a Caribbean island.
The main story follows a singer-songwriter beach bar bartender who enjoys the female tourists that stop by. Through the course of the show, he falls in love with a woman who is the exact opposite of him in every way. She’s all about trying to change the world and make something of her life, whereas he navigates the world in a more relaxed and carefree manner. The show explores if these two incredibly different people can ultimately get together.
The Parrot Heads in the crowd were excited to learn that Buffett’s hits including “Come Monday,” “Volcano,” “He Went to Paris,” “Cheeseburger in Paradise” and, of course, “Margaritaville” are all in the show. Boos and jeers made a lone appearance when Ashley said the song “A Pirate Looks at Forty” is not currently in the musical. Following the very vocal response, Ashley joked that it might be a different show by the time it arrives in Chicago.
In addition to featuring songs already recorded and released by Buffett, the show includes new songs written by Buffett for the characters. As for the other songs he wrote for the show that Ashley cut, Buffett assured those in attendance that they’ll be appearing on an album in the future.
Jones ended the evening by asking several questions previously submitted by fans in attendance. The first one likely brought the greatest relief to all in the theatre.
“What are you going to do when you retire? Are you ever going to retire?”
“No,” Buffett replied with a smile.
“Escape to Margaritaville” will play at the Oriental Theatre (24 W Randolph St.) Nov. 9-Dec. 2. Tickets cost $32-$162 and can be purchased now at Broadway in Chicago box offices by calling (800) 775-2000 and online at www.BroadwayInChicago.com.