Elton John, Paul Simon, Bono, Cindy Lauper and Sting: At one time or another all these immensely successful pop stars have succumbed to the irresistible siren song of the Broadway musical, with some finding greater success than others.

‘ESCAPE TO MARGARITAVILLE’
When: Nov. 9 – Dec. 2
Where: Oriental Theatre, 24 W. Randolph
Tickets: $33 – $120
Info: www.BroadwayInChicago.com

Now, Jimmy Buffett , the man with the Parrothead following that dreams of a laid back existence and a wardrobe of floral shirts, straw hats and flip-flops, is making his second go at the prize with “Escape to Margaritaville,” a musical that incorporates and expands upon his songbook. The show, with a book by television veterans Greg Garcia and Mike O’Malley, direction by Christopher Ashley (recipient of the 2017 Tony Award for his work on “Come From Away”), and choreography by Kelly Devine, opened in May at the La Jolla Playhouse. It has been on tour in the months since, and will arrive for a three-week “pre-Broadway” engagement at the Oriental Theatre on Nov. 9, with a New York opening set for the Marquis Theatre on Feb. 16, 2018.

Paul Alexander Nolan plays Tully and Alison Luff is Rachel in the Jimmy Buffett musical, “Escape to Margaritaville.” | Matthew Murphy

“Margaritaville” spins the story of Tully, who works as a singer/guitar player and bartender at a bandstand near the Margaritaville Hotel on some Caribbean island where each week a cruise ship deposits yet another flock of tourists. Among the crowd is at least one girl Tully (played by Paul Alexander Nolan) can charm until she boards the boat again about a week later — leaving him free of any commitment. But then, much to Tully’s surprise, that pattern is disrupted. The girl who grabs his heart is Rachel (Alison Luff), a passionate environmentalist and workaholic from Cincinnati who has come to the island for her friend Tammy’s bachelorette party, and nothing more. Things are about to change.

Buffett, the master “escapist” who, at the age of 70 is fit, trim and admittedly still driven (and capable of drawing a crowd of more than 40,000 fans to his arena concerts, as he did this past summer at Wrigley Field), is not quite the same man you might envision lounging in a hammock and sipping a salt-rimmed drink. Despite the fact that for decades his well-cultivated, low-key vibe has been an aspirational model for many, he is a deceptively Type-A guy.

An easy charmer — unpretentious, good-humored and talkative — Buffett is buoyed by the fact that his fans include both nostalgic Baby Boomers and a whole new younger generation. But do not be deceived by the man whose hit songs over the course of five decades include “Margaritaville,” “Cheeseburger in Paradise,” “Volcano,” “Come Monday,” and “My Head Hurts, My Feet Stink, and I Don’t Love Jesus.”

Buffett, who calls Sag Harbor, Long Island, home these days, laughs knowingly when it is suggested that in many ways he has far more in common with the character of Rachel than Tully. For in addition to a busy concert touring schedule that takes him to Europe and beyond, he has long been a successful businessman, with chains of restaurants keyed to his song’s themes, licensed products for everything from tequila to chips and guacamole, a beer deal with Anheuser-Busch, a casino-hotel in Atlantic City, and a $1 billion retirement village in Daytona Beach, Florida, now in the works. He also is involved in many charitable efforts, supporting ecological and marine laboratory projects and more recently raising money for hurricane relief.

But it is Broadway that calls to him.

“My love of musical theater dates back far longer than my interest in the music I am known for,” said Buffett, during a chat in Chicago. “I grew up in Mobile, Alabama, where my working mother, who had three kids, performed as part of the Mobile Theatre Guild, and she would drag me along to play children’s roles — like the little French-Polynesian boy in ‘South Pacific’ — and I kind of liked it. She also took me to see the road shows that came through town. I learned everything I know from Rodgers and Hammerstein — the way those songs go into your heart, the way the lyrics are like poetry but always driving the story and sounding authentic to the characters. I was a child of the television age, but I loved the live entertainment form.”

Mike O’Malley | Courtesy Broadway in Chicago

“I still remember the first time I saw ‘The Who’s Tommy’ on Broadway, and the original ‘Evita’ with Patti LuPone and Mandy Patinkin,” said Buffett. “And I began wondering if I could make a musical out of my own music, although I knew the challenge of doing it would be to be true to my audience as well as to connect to a new one.”

Buffett’s first (if unsuccessful ) attempt at a Broadway musical was two decades ago when he collaborated with Herman Wouk (fabled author of “The Caine Mutiny”), to create a musical based on Wouk’s book, “Don’t Stop the Carnival.” A paradise-turns-into-hell comedy about a man escaping to the Caribbean to salve a midlife crisis, it played for six weeks in Miami and closed, but Buffett turned it into an album.

“The daunting task for Greg [Garcia] and me was to find a story that could spin around Jimmy’s huge catalog from the 1960s until now,” said co-writer Mike O’Malley. “Jimmy has such an amazing ability to tap into what Americans really care about — relationships, family, friends — so we based our story around the clues we found in his songs. Some of his songs give you the license to chill out, but others are looking back on the night before chaos. There is quite a difference between a song like ‘Come Monday’ and ‘Cheeseburger in Paradise,’ and the songs on the ‘Coconut Telegraph’ album.”

For “Margaritaville” Buffett said he wanted the band to sound like a bar band, “mimicking the instrumentation of my own Coral Reefer Band, with most of the musicians placed on the stage and just a few in the pit.” The show also will feature some notably zany moments including flying scuba divers and a beach ball spectacular. A nice distraction from an approaching Chicago winter.

Lisa Howard (Tammy) and Eric Petersen (Brick) in “Escape to Margaritaville.” | Matthew Murphy