Kevin Flynn: Growing up in an Irish iron-worker family was good for about 50 percent laughs and 50 percent life lessons

Nov 13, 2021

Comedian Kevin Flynn’s latest one-man show is called Fear of Heights. He performs at The Rockwell in Somerville on Saturday, November 13 at 9:30 p.m.

Massachusetts comic and all-purpose talent Kevin Flynn has packed several exciting and impressive careers into the past 35 years or so.

He was a two-time captain of the University of Massachusetts soccer team in the mid-1980s and such a standout player that he immediately transitioned to pro soccer following his graduation from UMass. Three years in the Major Indoor Soccer League (MISL) evolved into a broadcast career covering World Cup Soccer for ABC, ESPN and Fox Sports, as well as producing and hosting a youth-oriented program for ESPN called Sports Figure.

Other programming and broadcast highlights included the 1996 creation of the Discovery Channel extreme adventure program Go For It, which enabled Flynn to conceive his first one-man show – the multiple award-winning comedy performance The Go For It Guy.

Tucked between his early milestone achievements in sport, broadcasting and live performance, Flynn appeared in films with Bill Murray, Ben Stiller, and Jim Carrey, and built enough comedy chops to win the Boston Comedy Riot in 1988 – a validation that really never expired and has enabled Flynn to appear on televised comedy specials and perform headlining shows at comedy clubs and on college campuses ever since.

He also is the Founder and Executive Director of the Nantucket Comedy Festival, which supports the island-based Stand Up & Learn™ comedy education program.

Flynn’s latest project, however, is another one-man show that uses both comedy and dramatic moments to give audiences a look into phobias, fears and relationships between fathers and sons – with Flynn’s own family experience serving as the prism. Flynn’s Fear of Heights—A Very Funny Phobia is in the midst of a national tour and is scheduled for a Saturday, November 13 performance as part of the Boston Comedy fest at The Rockwell in Somerville.

The busy performer recently took some time to exchange thoughts on his new show with fellow Boston-area entertainer and World Gone Crazy musical comedy performer Gary Marino, who kindly shares them with AHN here:

Gary Marino: Tell me about Fear Of heights?
Kevin Flynn: It’s a one hour and twenty minute one-man show with both pictures and some video as well. It a dramedy with both funny and serious moments and it takes you on a journey of my fathers life, his father and my own. It asks the question “What is True Success?” In my case what is important in life? Comedy or career success or more importantly love, family and giving back.

GM: What would you say are the most poignant lessons?
KF: Just the sacrifices my parents and relatives made for me to have a better life. In addition to the jobs they did they moved us from New York City to Connecticut, which was a big deal because my dad still worked in NYC. Iron workers had a tough life in those days…lots of physical wear and tear and injuries. They ALWAYS got injured. My dad used to take me to visit his smaller jobs. I never realized I had a bad fear of heights. I told him on his death bed. There’s also a story about a near death experience I had that helped me to appreciate what true success in life is.

GM: Would you say the younger generation has been getting a lot out of it?
KF: For sure. My daughter is 21. Your son if you bring him will too. again the show asks the most important question: “What Is Success In Life”?

GM: How long did it take you to write the show and get it ready for the stage?
KF: I started writing it just before Covid and it ended up being a lockdown project. My friend Judith Ivy – a Tony Award winner – helped me get it ready too.

GM: What percentage of this is stand-up comedy and what is serious message?
KF: It’s 50 percent comedic story telling and 50 percent serious message

GM: What’s The difference between performing a typical 50-minute stand-up headlining set and performing a one man show like this?
KF: Well for starters you don’t get to “work out” this material the way you do in the clubs for stand-up so it’s tougher. Also its a continuous storyline which takes you on a journey versus a stand-up comedy set. There’s a story arc and there’s life lessons.