Comedian, actor and writer Kevin Flynn brings his one-man comedy show, ‘Fear of Heights,’ to Key West Theater on Sunday, June 5. CONTRIBUTED

You know that famous black-and-white photo from 1932, “Lunch Atop a Skyscraper,” of 11 ironworkers having lunch on a steel beam 850 feet above Manhattan? 

The photo by Charles Clyde Ebbets is an icon of American ambition and industry. But for comedian, actor, writer and producer Kevin Flynn, it’s a family photo — and a full-time phobia.

The man on the far right, sitting on the end of the beam, is Flynn’s grandfather. And the location of the sky-high photo is the grandson’s greatest fear. It’s also the reason he didn’t follow in the sky-high footsteps of his forefathers. 

Key West audiences will reap the benefits of Flynn’s divergent career path, when he performs his one-man comedy show “Fear of Heights,” at 7 p.m. on Sunday, June 5 at Key West Theater. (Flynn will also perform three nights of stand-up comedy on June 2, 3 and 4 at 8:30 p.m. at Comedy Key West, 218 Whitehead St.) 

Instead of sitting atop skyscrapers, Flynn remained on solid ground by becoming a professional soccer player. He’s now an award-winning actor, writer, producer, sports show host and comedian, having made the transition to stand-up comedian by winning the prestigious Boston Comedy Riot. Since then, he has made numerous TV and film appearances as a comedian and actor.

Flynn can be seen as the wedding coordinator in “The Heartbreak Kid” with Ben Stiller. He’s also been in in “Me, Myself and Irene” with Jim Carrey; “Osmosis Jones” with Bill Murray, and as Charlotte’s boyfriend in HBO’s “Sex and the City.” (His character, Bram Walker, was voted one of the series’ most popular boyfriends.)  

While constantly acting and performing stand-up around the country, Flynn also works as a host and entertainer in the sports world, having covered World Cup Soccer for Fox Sports, ESPN and ABC. His show, “SportsFigures” on ESPN, received the Polk Award for excellence in children’s programming. He also created an award-winning weekly sports podcast for the ESPN Network called “Over the Ball,” which combines soccer, comedy and entertainment.

In 1996, Flynn hosted The Discovery Channel’s “Go For It,” an extreme outdoor adventure show in which he swam with sharks, jumped out of airplanes and scaled dangerous peaks. The show led him to create his first one-man show, “The Go For It Guy,” which won the Best of Fest at the Boston Comedy Festival and HBO’s U.S. Comedy Arts Festival in Aspen, Colorado.

What: Comedian Kevin Flynn’s one-man show “Fear of Heights”

When: 7 p.m. Sunday, June 5

Where: Key West Theater, 512 Eaton St. 

Tickets: $35 @

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Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.