Interview with Michael Kosta, author of “Lucky Loser”

On March 22, Michael Kosta—author, comedian, and former tennis player—visited the Barnes & Noble in Palm Beach Gardens, FL, to talk about his new book Lucky Loser: Adventures in Tennis and Comedy (Harper, 2025). You may recognize Kosta from The Daily Show, where he is a correspondent, or you may recognize him from the professional tennis circuit, where he once ranked 864 in the world. At his book talk, he read from Lucky Loser and answered questions about comedy as art, the differences between making it in tennis and making it in comedy, and the pros and cons of pickleball. After his reading, Grace Mackey got the chance to chat with him for a few minutes.

You're not from Florida originally, but what is your favorite thing about the state?

There's an amazing book, I believe called The Swamp, about the founding of Florida, and how this state really should just be underwater and not have 32 million people in it. Florida is fascinating. My five-year-old daughter asked me the other day, “What is Florida?” and I was like, “That is a very complicated question and I don't even know the answer to that.” I played a lot of tennis in Florida growing up. It's so many things. It's so American. The fact that so much of this is taken by colonizers of native land is so American, and some people don't even understand that water and controlling nature is so relevant to the state. And those might not be your answer, but that is super complicated and fascinating to me. It is also one of the best tennis states to exist.

In your book, it sounds like you document some failures or embarrassing moments in your life. Why is it important for people to read about moments like this? And do you think people write about them enough?

It was very important for me to write about it. I wanted everybody, especially the younger generation, to realize embarrassing stuff happens and failures happen and it's not the end of your life. I reveal some very embarrassing stuff in this book, hoping that other people go, “Oh yeah, I did something similar. I'm not alone. This can be helpful to me.” People should be reading more about this stuff, if they aren't already.

Why is comedy important?

 Well, if you don't have comedy, it all feels very serious. And I think it keeps you in the present moment. When you're laughing, you are present. That's my favorite part about performing in a comedy club: I'm making people laugh. It's the one time in our day when we're not mad about the past or worried about the future. We're just right in the present moment and there's something so beautiful about humans laughing together. It's so connective. I love that.

David Foster Wallace also played tennis. Is there something about tennis that you think connects to writing and thinking or?

I think people who play tennis in general are pretty smart. I don't want to pat myself on the back, but, David Foster Wallace, that mind, oh my gosh. I think they’re analytical. You play, but then you have time to think about it. And I think it's a beautiful sport. In a lot of ways, that might be writing, too: beautiful and analytical. I don't know about the correlation, but it's fun to explore that.

Who are some authors who have influenced you?

Well, David Foster Wallace, for sure. I don't write anything like him. I wish I did, but he's an excellent mind and wonderful writer. He's from Urbana, IL, and I went to University of Illinois, so I was aware of his writing even then. I love Andre Agassi's Open book. I think that was a really excellent, revealing memoir. Then that book, The Swamp. I forget who wrote it, Michael somebody. [Michael Grunwald] Those are the three books that pop into my mind right now.

Do you think being an athlete has made you a better writer? If so, how?

You know, I wish I would have spent less time doing sports and more time writing, but I think being an athlete teaches you so many important lessons without real stakes. Like there's no life or death stakes. If you lose the match, it's like everything's fine, but you do learn things like, “Hey, discipline is important,” and “hey, I know today wasn't the best practice, but you got through it.” And so much of writing a book is clicking the keys just to get going. You have to try not to be too analytical in the sense of editing yourself while you write. Just be in the moment and write. And that's very very “sport.” You can debilitate yourself with “Why did I do that?” sure, but it’s like, just play. So much of writing to me is, “Just get the job done,” which I attribute to sports for sure.

What is the main thing you hope your readers take away from your book?

 The first thing I want them to do is laugh. 100% the first goal. And each chapter does have a little bit of a message or, I don't want to say advice, but a reflection on life. So, the best case scenario is they've laughed and then they go, “Oh yeah, that is a good point. I'm going to do that,” or, “Oh, yeah, that helps me in my life moving forward.”

Interview conducted by Grace Mackey