Comedian, actor, and writer Kevin Flynn presents his one-man comedy show, “Fear of Heights,” at the Key West Theater on Sunday, June 5.

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

The photo of 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, seated at the end of the beam, is Flynn’s grandfather. And the location of the dizzying photo is the grandson’s biggest fear. This is also the reason why he did not follow in the dizzying footsteps of his ancestors.

Key West audiences will reap the rewards of Flynn’s divergent career path, when he performs his one-man show, “Fear of Heights,” at 7 p.m. on Sunday, June 5 at the Key West Theater. (Flynn will also present 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 on top of skyscrapers, Flynn stayed on solid ground by becoming a professional footballer. He’s now an award-winning actor, writer, producer, sports host and comedian, having transitioned into stand-up comedy by winning the prestigious Boston Comedy Riot. Since then, he has made numerous television and film appearances as a comedian and actor.

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

While constantly acting and performing around the country, Flynn also works as a host and entertainer in the sports world, having covered the Soccer World Cup 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 football, 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 from planes and climbed dangerous peaks. The show led him to create his first solo show, “The Go For It Guy”, which won Best of Fest at the Boston Comedy Festival and HBO’s US 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 Theatre, 512 Eaton St.

Tickets: $35 @ thekeywesttheatre.com