Tom Leopold is a comedy writer based in New York City. He has written for TV shows including Seinfeld, Will & Grace, and Cheers and has written for comedians including Bill Murray, David Letterman, Carol Burnett, and Mary Tyler Moore. He is also the author of three novels: Almost Like Being Here, Somebody Sing, and Milt and Marty: The Longest Lasting and Least Successful Comedy Writing Duo in Showbiz History. His other credits include co-writing the musical J. Edgar!, which starred Kelsey Grammer, John Goodman, and Christopher Guest. Currently, Leopold teaches the “Comedy Writers’ Room,” a private master class in TV writing, which he has taught at Columbia University and elsewhere.
What is the most important thing you’ve learned about writing?
I’ve written novels and I’ve written all other kinds of things, but I want to speak as a comedy writer, though I think this applies to any kind of writing. If you want to touch people, if you want to steer people, if you want to give them adventure – using comedy writing as an example – make sure you think it’s funny. Now, of course, that’s the obvious thing, right? But so often comedy writers get stuck in writing what they think others might think is funny or what is funny at the moment.
Instead of that – and it’s scary – if you absolutely go with what really, really makes you laugh, there’s a chance other people won’t, because you’re being so specific. But, of course, the more specific you are in writing, the more general an audience can react to it. It’s like poetry. The more specific the poem, the more general it is. It’s the same in other genres, too. If you’re writing a suspense novel, make sure you’re in suspense. It’s very simple, but it’s important for a lot of reasons. One is you’ll know how to do it again. So often I’ve worked on shows and pilots, and you want to write what really amuses you, what really moves you. Because then, let’s say you’re doing episode 120, you know that you have a well to draw from, because it’s coming out of you. I know it’s a cliché, but it’s a really great cliché. Have the nerve to write the thing that absolutely drives you crazy, or you love, or you think is hysterical. Because none of us are so original that there won’t be a big swatch of people out there who agree.
I also find that thinking of it that way helps you with rejection. God knows in 50 years of writing, I’ve had plenty of that. Then at least you go down with what you thought was great, or as good as you could get it. There’s a little bit of peace in that. It still makes you double up in pain, but it’s easier to live with.
But when you find those people who really spark to it, you know that you’re on that same wavelength, and it’s the only real wavelength you’ve got. And it takes some guts, you know? Because wow, I’m really putting myself out there. And how else can you really do it? Painful as it is, you might as well go all the way. As painful as writing is anyway, you might as well invest it with yourself.
And how has that helped you as a writer?
It’s really helped me deal with rejection. I always say that I’ve been luckier than a lot. I’ve never had a job outside of showbiz, and so I’ve been really blessed that I’ve been able to make a living out of it. But I also say that 94 percent of my career has been disappointment. But that other 6 percent was a gas. It really was. I think that as painful as it is, rejected scripts are like what painters, artists must feel when they go to a gallery, they put their paintings up on the wall, and they don’t sell, so they put them back in their beat-up old Volkswagen and take them home. I have a lot of scripts like that. And sometimes I think, ‘Man, I loved that script. I still love that script.’ Maybe there’ll be a life for it later, or maybe its time will come. And boy, I’d rather have a shelf of unproduced stuff that I love than a shelf of unproduced stuff in which I tried to outsmart the audience – outsmart the buyer, if you will.
With rejection, you never expect it. And maybe that 94 percent is a high number I’m using as a joke. But even so, you never expect it. I think that’s what makes us such idiots. Because every single time, I think the world’s gonna fall in love with what I’ve written, and mostly they don’t, and I’m disappointed and surprised every time. And you think I would learn. But the thing is, I don’t think you can keep doing this if you don’t keep falling in love with these little babies that you create, that maybe nobody else will like.
—Gabriel Packard is the author of The Painted Ocean: A Novel published by Corsair, an imprint of Little, Brown.