Laugh away the January blues with a new comedy special from acclaimed New York comedian Kevin James Doyle Diary of a Bald Kid – out now on Amazon Prime Video. A Youngish Perspective has the privilege to have this exclusive conversation with Kevin.
Kevin, in ‘Fool Proof,’ you dive into the theme of risk—what’s the riskiest decision you’ve ever made purely for a laugh on stage, and did it pay off or backfire spectacularly?
The first time I just told a very embarrassing story onstage, as it actually happened in real life, it turned the humiliation into humour. But it was super risky. It always feels risky on stage to be honest about something but it’s always paid off. All the dumb things I have done or said or unfortunate situations I have found myself in, tend to elicit laughter from people. I have never taken a risk on stage that has backfired. It may not go perfectly, but it always gives me more confidence to dig deeper and care less about what the audience things and more about the truth and humor of the situation or joke.
Motorcycle theft, green card marriages, and insurance companies—your comedy really spans some wild terrain! If you had to face off against one of these in a battle of wits, which do you think you’d outsmart most easily?
I would happily go toe to toe with insurance companies and their ethics and incentives in a public debate and I would win. I would outsmart them through the nonsense of their own policies. The joke / story about dealing with the insurance company is one of my proudest moments on stage because it truly infuriated me in real life and to get to expel some of my rage in a show felt great and I always get people that talk to me about their own negative experiences with insurance companies after that show.
In ‘After Endgame,’ you take comedy into the world of high-stakes chess. If comedy itself were a chess game, what’s been your boldest ‘checkmate’ moment on stage where you knew you’d completely won over the audience?
Fool Proof and After Endgame both have audience interaction moments that are more than they seem at the time. They tie into the overall theme and are like their own little plot twist. I think I got the ideas to add things like those from seeing so many amazing shows at Fringe over the years. Setting up a joke early in the show that is there to pay off later is my absolute favorite thing to do in my shows and it always feels like a checkmate moment. Taking the audience on a journey and they have no idea I am walking them right over a trap door that is about to open.
You’ve said ‘Fool Proof’ questions what risks are worth taking—what’s a risk you took in life that felt completely reckless at the time but shaped you as a comedian or person?
The first year I moved to New York was very very unsatisfying as an actor. Auditioning was not fun or fulfilling or creative. In 2012 I stopped auditioning or trying to make it as an actor anyway and focused on comedy. It was counterintuitive because, honestly, I would still love to act on stage and in film. But at the time I just trusted that developing the skills as a joke writer, storyteller and performer on stage would eventually lead me back to acting. I am very thankful for comedy for giving me something that has been so creative and fulfilling, instead of auditioning which just put me into a ‘please pick me’ mentality. I would have never thought of myself as a writer a decade ago and now I identify more as a writer than an actor and stopping auditioning helped open my mind to that.
Your new material touches on love, death, and fear—pretty big life themes! If you had to explain the show’s message using only chess piece metaphors, how would you break it down?
The new show After Endgame is all about how much more powerful you are when you are working together with others. One of the great chess moves of all time is 1956 Bobby Fischer sacrifices his queen (the most powerful piece) and goes on to win the game. Pawns are the weakest piece but when they are together they are quite strong and can eventually win you the game in the end. In my past 2 shows they are both about finding the joy and silver lining in very painful bad experiences and the metaphors in chess are endless about perceived weakness being a strength or taking a bad situation and turning it to something good. Or losing a battle but winning a greater prize in the long run.
Since your show ‘After Endgame’ explores teaching chess to the ultra-wealthy, what’s the strangest or most unexpected reaction you got when explaining a chess strategy during those lessons?
A lot of people want to learn chess because of its perception as an intellectual game for the smartest people. But I am very very serious when I say that the best thing in the world you can have is a friend to play a game with. Not a computer, not an enemy to defeat, but a friend who over the years you can play many games with and have a wonderful rivalry. I have this with many friends in backgammon and we have formed a competitive relationship over the 100’s of games we have played. And that has taught me more than any individual game or strategy. I think a lot of people think the benefit of a game is intellectual but I think the benefits are more emotional and social and spiritual.

