The company of Chicago Shakespeare Theater’s production of Shakespeare’s "Twelfth Night," reimagined in the Caribbean by director Tyrone Phillips. Credit: Liz Lauren

NAVY PIER — Winter may be approaching, but you can still bask in the warmth of “Twelfth Night,” which recently opened in the Courtyard Theater at the Chicago Shakespeare Theater on Navy Pier.

In director Tyrone Phillips’ version of the classic Shakespearean comedy, the hilarious and romantic play filled with missed connections and misunderstandings is set against the backdrop of the Caribbean, complete with storms, sands, colorful tropical garb and yes, plenty of Bob Marley music.

“Twelfth Night” focuses on love, but also on a series of miscommunications and fluid gender roles that fits right into today’s landscape. Twins Viola (Jaeda LaVonne) and Sebastian (Justen Ross) become separated when their ship goes down at sea. Viola is shipwrecked on the island of Illyria, where she changes her persona and becomes a manservant named Cesario to the handsome Duke Orsini (Yao Dogbe), who she quickly falls for. But the Duke is besotted with Olivia (Christiana Clark, a showstopper), who in turn falls in love with Viola-as-Cesario.

That romantic love triangle is buoyed by the hilarious antics of the gifted cast, a setting so sunny you can almost feel the heat emanating from the stage, and that effervescent soundtrack (there’s even a playlist on Spotify). For example, the inclusion of Marley’s “Is This Love,” highlights the confusion of various affectionate feelings among the characters.

Director Tyrone Phillips with fight choreographer Matt Hawkins in rehearsal for “Twelfth Night” at Chicago Shakespeare Theater. Credit: Joe Mazza – Bravelux

A first-generation Jamaican American, Phillips told Block Club that as he was preparing the play, “Taking that island, and setting it in the Caribbean — that was my north star. That was a very clear moment. … I thought about love and I thought about music. I thought about Caribbean Americans. Jamaicans are some of the funniest people in my life, like a comedy, all of it.

“So I said, ‘Okay, how do I take a piece of myself? And an homage not only to my mom, but my wife as well, expressions of love.’”

“Twelfth Night” marks Tyrone Phillips’ first time directing on the Chicago Shakespeare stage. He’s also the creative director of the Definition Theatre company, which is currently working on building a community theater in Woodlawn: “We’re super excited. Our theater is a theater company, community center and entrepreneur incubator. It’s all of those things coming together. We see arts and economic development coming together to revitalize the community.”

Phillips is no stranger to Shakespeare: His history with the Bard goes all the way back to playing Othello in high school at Niles North. Then while studying acting at the University of Illinois in Urbana-Champaign, he spent some time abroad in London, where he studied at Shakespeare’s Globe Theater.

“For me in the beginning, I did see Shakespeare as the hardest thing to do in theater,” Phillips said. “But at the same time, I thought about all people who have a living just doing Shakespeare, right? So that was interesting to me in our industry to say, ‘Well, someone cares about it.’ It’s lasted long enough that audiences still love it.

“So I think I started loving it more as I started taking away the barriers, when I realized it was poetry. It’s music. It’s about the rhythm and the pacing. It’s about the fight between man versus man, man versus self, man versus universe, all those stories are told. You see the love, you see violence, you see war — he covers the human experience, which is why it keeps staying relevant to us. So when I studied abroad at the Globe, that changed my life.”

Phillips’ “Twelfth Night” aptly translates that poetry to the stage, particularly in various characters’ soliloquies that are mesmerizingly lyrical. But that language is augmented by over-the-top, almost slapstick gestures and business from the players, making the play riotously funny on top of its Elizabethan English.

Couples Viola (Jaeda LaVonne) and Orsino (Yao Dogbe) and Olivia (Christiana Clark) and Sebastian (Justen Ross) in Chicago Shakespeare Theater’s production of “Twelfth Night.” Credit: Liz Lauren

Phillips said of his Olivia, “Christiana Clark was not afraid. She’s like, ‘How big do we go?” I said, ‘Come on, let’s go — the stage is big!’

“For us, truly, it was about the humanity and about the joy,” the director said. “We’re living in a really rough time. And so we as a cast we talked about how it’s going to be cold in the beginning. The given circumstances of our world are not beautiful. And then it will be sunny and great.”

The boisterous, energetic show certainly offers an unusual take on a Shakespeare production — an effort not without risk. But on opening night, Phillips had a special barometer in the Courtyard Theater to let him know how the show was going.

“There were two kids in front on opening night. Most of my time, I was checking in with them. And to see them literally just full-on belly-laughing at Shakespeare, it was like, something special is happening.”

“Twelfth Night” runs every day except Mondays and Thanksgiving Day through Dec. 3 at Chicago Shakespeare Theater on Navy Pier, 800 E. Grand Ave. Evening performances are at 7:30 p.m., with matinees available on Saturdays, Sundays and Wednesdays. Tickets start at $63. For more information and to purchase tickets, visit the Chicago Shakespeare Theater website.

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Arts & Culture Editor Twitter @gwenemarie