Flynn, founder and executive director of the annual Nantucket Comedy Festival, more recently hosted the soccer podcast, “Over the Ball,” which was named WorldSoccerTalk.com Best Radio Show of the 2014 MLS Season while on SiriusXM before moving to ESPN, where it ran through February 2017.
Flynn will headline a “Coaches Convention Comedy Special” at Paddy Whacks with Mark Riccadonna and Joel Richardson on Jan. 17 in Philadelphia, where the annual United Soccer Coaches Convention takes place Jan. 17-21.
SOCCER AMERICA: How’d you feel after the USA failed to qualify for the 2018 World Cup?
KEVIN FLYNN: I was depressed when the boys failed to qualify, and I found myself once again defending the game to people who were not only ignorant to it but also seemed to be rooting for its failure. These are the people who used to think the World Cup was a large piece of athletic equipment.
Some of the comments I overheard reminded me of the limited knowledge in this country of both soccer and anything international. "We lost to Trinidad and Tobago? Is that a country? Sounds more like a skin rash” -- was one of my particular non-favorites. “More people attended my high school than that entire country, how could we lose to them?”
It continued ... “I mean, come on, how can we lose to Costa Rica in anything!” … “We beat St. Vincent & the Grenadines? That’s awesome! Is that a Boy’s Catholic High School or one of the ingredients in a Shirley Temple?" These comments aside, a lot more people in this country now realize the difficulty of this whole World Cup qualifying process.
Before this loss, most younger Americans thought qualifying was just a given. Our right. Well, it’s not. And just look at where the Dutch and the Italians find themselves. These countries, where the sport is dominant in their culture, are not going to Russia either.
Let’s rewind a bit. During the 1994 World Cup you appeared at halftime of every game. How'd you get to every stadium in time for the show?
Well, I’m very, very quick, Mike. No, they would beam me via satellite to all the stadiums around the country, appearing on the big screen, to tell one stadium what was happening in the other stadiums. I don’t know if you’ve ever been “beamed,” Mike, but it's a lot of fun.
How’d you get that gig?
I sent an unsolicited “demo” tape to the powers that be at ESPN. The tape, and it was a “tape” which speaks to how long ago it was, contained some of the goals I had scored in the indoor league, alongside some of my standup comedy television appearances. It worked. They hired me straight away to do a bunch of light-hearted, comedic stories explaining various elements of the game to the U.S. public in preparation for the World Cup.
Your pieces on “Road to the World Cup,” Brent Musburger, led to you becoming “The Halftime Guy” …
Working during the 1994 World Cup is something I will never forget. The only problem was that I could not actually go and sit in the stadiums for any of the games. I was locked in a bunker at the International Broadcast Center in Dallas. It was this freezing dark cavernous studio. It was like going to work every day and hanging out in a meat locker.
I tried to bring some humor and an American perspective to the game and to the highlights. The feedback that I got was tremendous. Soccer players and the overall soccer community are a very hip group and I was pleased that they liked what I was doing. If it wasn't any good, believe me, I would have heard about it from all my soccer buddies.
Kevin Flynn with Ben Stiller (left) in "The Heartbreak Kid." Flynn also appeared in “Me, Myself and Irene” and HBO's “Sex and the City.”
You captained UMass back in the 1980s, how good a player were you?
I can honestly say that I was a good college player. Unfortunately, I didn't start playing soccer until I was 14, in the 8th grade, and I obviously had a lot of ground to make up. I was actually the starting tailback on my town’s football team and on my way home from football practice one day on my bike, I just happened to see a bunch of guys kicking around a soccer ball. For the last half of that football season, I would wear soccer stuff underneath my pads and when football practice was over I would jump into the pick-up game.
I fell in love with the game straight away. Soccer became my main focus from that point on. It confused my Dad at first. He was a big gridiron football fan. I used to joke that when he first started coming to my soccer games he would stand on the sidelines and yell, “Pick up the ball! Pick it up and hit somebody!” My Dad did come to love and appreciate the game and became my biggest supporter.
Why did you never get selected to the national team?
Politics! The fix was in! I had a head cold! I didn’t hear the whistle! No. Actually, there were a lot of other reasons. The main one is that I just wasn’t good enough. I did manage to play for the East in National Sports Festival Games. During my junior summer in college while playing in Europe, I was offered a contract to stay in Belgium.
The opportunity to get some professional experience in 1984 when I graduated college was virtually non-existent. The NASL had folded and all those players were kicking around with nowhere to go, nowhere to play. The [indoor] MISL was shrinking too. The NPSL/AISA was quickly becoming the only place to play. And it was a rough ride for an American college player to get even a sniff of a tryout back then.
Sports Festival East team: Flynn is the middle player, back row, to the right of Hermann Trophy winner Tom Kain.
But you starred in professional indoor soccer?
I wouldn’t claim to be a “star.” I played three seasons in the indoor league and they still remain some of my best soccer memories. I still have so many friends from those days. But as the saying goes, they were the best of times and the worst of times. We were not paid much, but we were doing what we loved and were fighting like hell to be respected as athletes and for the sport of soccer to be taken seriously.
It was right in the middle of a dark period for U.S. professional soccer. We traveled by bus, ate lots of fast food, played somewhat frenetic soccer in front of two or three thousand spectators on turf that was laid down on top of a freezing cold sheet of ice. But we loved it.
I also think it was the one place that maintained a professional soccer presence at that time in this country. Most importantly I believe it produced a lot of the next generation of coaches. Mike Noonan at Clemson, Dave Masur at St. John’s, Sasho Cirovsko at Maryland, Keith Tozer, now the U.S. futsal national team coach. … I could go on and on.
Any memorable low-lights?
I once got into an on-field altercation with a guy named Tom Alioto who played for the Louisville Thunder. I thought he came in really hard with a particularly cheap tackle. When he started to get up, I put him in a headlock and threw a quick rabbit punch. My fist came flying up, skimmed off the top of Tom’s head and I hit myself straight in the nose, breaking it.
Tom hadn’t thrown a single punch, but the referee took one look at my nose and threw us both out of the game.
Tom looked at the ref and said, ”But I didn't do anything?!” The ref said, “Yeah, sure, you didn't do anything, and I suppose he gave himself that bloody nose! Get out of here.”
Tom and I have been in contact and laugh about it all now.
You were an assistant coach at Boston University and coached youth soccer. Was your comedic talent an attribute for coaching?
Absolutely, humor can help in every aspect of one’s life. In fact, I’ve developed an educational program called “Standup & Learn” that teaches young ones how to build confidence and self-esteem through standup comedy and storytelling. In coaching and in teaching, humor always helps. I have made a pretty good living as a professional comedian over the past 30 years and am actually fortunate to consider some of the top comedians in the world as personal friends. That includes Lewis Black, Jim Gaffigan, Brian Regan, The Farrelly Brothers. I still maintain, though, that the funniest guys I have ever hung out with were soccer players.
How did your comedian career begin?
I began to write standup comedy on those long roadtrips during my last two years playing ball in the NPSL. I started to enjoy making my teammates laugh as much as I enjoyed playing the game itself. After three years of playing, I felt it was time to move on. I enrolled in the Graduate School of Broadcast Journalism at Boston University, where I was Coach Neil Roberts’ assistant coach. It was during that time that I had taken all that I had written and started to try it out on the comedy stages of Boston.
At the end of the first year, I won a competition called the Boston Comedy Riot alongside the women’s winner Janeane Garofalo.
I was given about 10 weeks of professional road work at that time, as well as being given the opportunity to open for Jay Leno, Jerry Seinfeld, Rich Jeni and Bill Hicks.
The soccer season had come to an end, so I decided to drop out of grad school and hit the road for a few weeks with Janeane. It was like being back on the team bus only not nearly as funny or fun.
What was your most enjoyable soccer TV work?
I think that it would have to be the 1994 World Cup stuff that I did for ESPN and ABC. The game and the World Cup was just so new to most people here in this country that I was basically given a blank slate to create and produce whatever story I wanted. I had full access to the national team and actually got to knock it around and play with the guys in the development of some of those stories. Something I couldn't even get close to doing now, for a number of reasons.
I mean, I actually got pulled off the sidelines by Coach Bora Milutinovic and thrown into a full national side scrimmage.
Unfortunately, I also got in the net and took shots with Tony Meola and Brad Friedel for a story and broke two ribs in the process. Of course, I didn't let them know that fact until a few years later.
What did you enjoy most about the podcast?
We kept things fast moving with humor and lots of discussion with several different types of guests. I would mix it up with guests from the broader sports segment -- not just soccer -- and I would also have on guests from the world of entertainment, comedy and even politics. On one show, I would have on someone like The Great (and I really mean that) Bob Ley and then mix it up with a comedian like Jim Gaffigan, Billy Burr or The Farrelly Brothers and then throw in Joe Scarborough, who would want to talk about his beloved Liverpool.
Mainly, I came at it from an American perspective, wanting to cover things besides the Premier League and La Liga, which seemed to already be talked about quite a bit.
What do you think of the quality of TV soccer commentary today?
It’s getting better. I think it works the same as developing players really. Television outlets have to work with and give opportunities to new and young broadcasters to develop some true American voices for the game. If they do that, we can begin to create a real American style.
Who are some of the soccer TV personalities you admire?
During my year and a half at ESPN, I got to know and work with a lot of the guys over there. And they are really some great dudes.
Taylor Twellman, Brian McBride -- two American legends who I could chew the fat with on just about any subject from the national team, to youth soccer to college soccer. Taylor and I have since teamed up for a yearly standup comedy show in Boston that raises funds and awareness for Taylor’s ThinkTaylor Foundation called “Comics for Concussions.”
Craig Burley always cracked me up. I found him really fun, opinionated and knowledgeable along with Liverpool legend Stevie Nicol. I actually wanted to put those two together for a night in a theater just telling stories. It would have been great.
I would have been there to interpret from English to Scottish! I can always understand those guys perfectly but when they speak to each other you do sometimes need an interpreter, especially if we’ve all had a few beers.
Shaka Hislop is a class act as well. I used to say he is like the Trinidad & Tobago version of James Bond. And Shaka, just like Alejandro Moreno, played college ball here, so I think they have a really good overall American soccer perspective as well. I also got to know Julie Foudy when she was at ESPN for the summer covering the Women’s World Cup. What an impressive person she is.
Which coaches or players do you think could be stand-up comedians?
Well, Craig Burley and Stevie Nicol, as I said, would be a great comedy team. Dominic Kinnear is another one. I actually helped him get up on a stage in L.A. back in ‘94. He really hit it out of the park. He talked about getting his appendix taken out while in China with the national team. The name of his doctor was actually, “Dr. Oww,” I kid you not.
John Harkes is funny. He’s quick-witted and can do a lot of the funny faces and voices. He is also always in a constant busting-chops mode, which reminds me of a lot of the Boston comics I know and hang out with.
Any soccer jokes in your routine? Can you share?
Well, I actually did a few soccer jokes on one of my early television specials, “Evening at The Improv.” I think it was something like, “I played three years of professional soccer. I would have been more well known if I had entered the witness protection program. After playing three seasons, I announced my retirement. Well, by announcing my retirement I mean I told my parents.”
Not some of my best stuff obviously!
Are there any other comedians on tour who are soccer fans?
Judah Friedlander is a soccer fan and a guy who had some real foot skills apparently. It’s funny, Judah and I used to talk in the comedy clubs about the national team all the time but we would be the only ones. The other comics would be watching the Yankees and would look at us like we were talking Zulu or something. What has been great to see is that a lot of the guys are now really invested in the game and how the U.S. team does. A lot of them also now go to NYCFC games. Quite a change.
Are you running for U.S. Soccer President?
No. I think I’m the only former player who’s actually not running.
Name one thing you’d like to see improve in American soccer.
Let’s make the game and the coverage of the game more entertaining. Lighten up, loosen up and let’s have the confidence to put more of an American spin on it. American soccer is at an extremely important time in the development of the game here. American football is in a downward slide, and rightly so, and we can and should fill that void in the American sports landscape.
I truly believe that soccer can be the main American game in 20 years.