Humor and Rabbit Holes: An Interview with Leland Gregory

“We basically lie for a living. We make shit up all the time, and people give us money. It’s a great deal.”

Leland Gregory is the two-time New York Times bestselling author of Stupid American History and America’s Dumbest Criminals and a former writer for Saturday Night Live. Leland has authored more than 20 books, many of them national bestsellers. He has written and sold a screenplay to Disney and optioned another screenplay to Touchstone. He co-created the nationally syndicated TV series America’s Dumbest Criminals ( five years in syndication) and served as head writer and co-executive producer for the PBS series The Whole Truth. He has created advertising campaigns for national corporations such as Hyundai, Captain D’s, International Paper, Cracker Barrel, Dollar General, AT&T, and many more, and has contributed to such publications as Reader’s Digest, George, Playboy, and Maxim. He is a nationally renowned political media consultant who won the Gold Pollie Award for Overall television campaign in an infamous Senate race.

Do you remember the first story you ever wrote?

I vaguely remember the first story I wrote, but I didn’t really write it; I improvised it in front of my class. It was like fourth or fifth grade. My teacher, Ms. Patterson, who I loved, realized that I was good with basically making up shit. So, at the end of the school year, she asked me to come up to the front of the class and make up a story. So, I did, and the bell rang before it was over, and the students came up to me and go, “How does it end?” It’s like, “I don’t know, I’m making this shit up!” And that’s when I got my first taste of improv and writing.

Was that one of the first moments that you connected with storytelling, or did that come later?

No, it was really the first time ’cause she encouraged it. She saw it and instead of just talking to my parents and going, “He has a very good imagination, he’s very verbose,” she made me get up in front of the class, and I did. Which I’m sure a lot of students would be like, “Ehhhh…” So, I’m a ham. That’s the short of it right there. Just pay attention to me.

So, how long have you been professionally writing stories? And what kind of stories do you find yourself becoming passionate about? I wonder because you’ve done a lot of stuff. Like, you’ve optioned screenplays to Disney and Touchstone, but you’ve also written on SNL, so you have a wide range of writing. So I wonder what kinds of stories spark the most joy in you?

I’ve been writing professionally most, if not all of my adult life, whatever that is. Now, I didn’t take classes at college for it. I went into theater, foolishly enough. And then left the first semester because I thought, “Even if I’m a great actor, I’m still gonna be broke.” So, I went into Mass Comm, and look at me now. But I used to write even when I wasn’t getting paid to write. I would just write shit. In fact, I remember on lunch breaks in high school, I was so dorky I didn’t even sit at the chess table; I sat by myself and wrote stories. I made up jokes. I like sketches or skits, whatever you want to call them. Those are my favorite because you get in, set it up, make people laugh, leave. I love comedy. That’s what I primarily am drawn to so most of my writing is comedy. However, I’ll write anything. I’ve written for politics, written comedy, written documentaries. I’ve written commercials, I’ve written for newspapers, I’ve written for magazines. I’ve written books, TV movies, radio. So, basically anything that needs writing I can do it. Except technical writing. Don’t ask me.

What drove you to the outlet of screenwriting? Also, what has kept you so invested in it for all these years to the point where you teach it now?

Well, I was a kid of television. Grew up in the 60s, black and white TV, three channels and PBS, but that doesn’t really count. So, I loved stories, and I loved visual storytelling, so that’s why I was attracted to television. And then I started watching movies, my first movie was Blackbeard, which was a terrifying pirate movie my freakin’ aunt took me to. I love the structure of movies, how people tell the story. And how we’ve told stories in that act 1, act 2, act 3 format forever! I’ve always wanted to do that. My truth is, I always wanted to be Dick Van Dyke and live in upstate New York and write with Buddy and Sally in the morning, and then go home to my beautiful wife who wears toreador pants. That’s all I ever wanted, and I got it and then — then I lost it. I still have the pants. But that’s what I wanted. I wanted to be in that creative environment and come up with stories and laugh with people and it’s just … I was going to say it’s better than heroin, but I haven’t tried heroin yet so get back to me later and we’ll see.

There’s something really beautiful and cool, and sometimes weird, about the history of our medium because there’s a lot of weird stuff that’s still stuck around. For example, a lot of the lingo that we use is so old. When I first started taking classes it would bug me, but now, I think that it’s kind of cool that we still have a lot of that mixed into what we do.

Yeah, screenwriting is still typewriter based. It’s Courier at 12 points, and uppercase and lowercase are from printing days. So, it’s really this cool history of writing implements from a stick in mud to a chicken feather to quill pens, you know. And the king of them all, the Eberhard Fabor 602 pencil.

Ah, yes. The ones you collect.

Yes. I love everything about our medium. I love the sound of a typewriter; I love the sound of a keyboard. I don’t really handwrite that much because my handwriting’s hideous.

Is it cool, is it weird, is it freaky to take a medium that you’ve been so familiar with and be able to pass it on to people that are in my generation?

It’s all of those. It’s cool, weird, strange, unusual, imposter syndrome-y. Because it’s like, “Who am I to teach these young, vulnerable minds?” And that’s all I’ve got is a young, vulnerable mind. And I didn’t think I would. I didn’t think I was qualified to teach.

Why not?

Well because I’ve just never been a teacher. I didn’t care for being a boss or being in charge of a writing session. I always just let it go. But I just kind of fell into a niche and just fell in love with the structure. And then I thought, “Well, I can tell people how to do this.” And then students told me, “Just tell me your stories. You don’t have to teach me how to write. Just tell me how you did it and I’ll learn from that.” And that’s what I’ll find the most useful for them. I’ll tell people how I got from graduating from MTSU in 1983 to writing for Saturday Night Live and about that transition, and I think a lot of students need to hear that. They don’t care what’s in a book. That’s why I don’t require books in my class. But now I’m astounded that I’m actually in a position to teach students and that I like it and that they seem to like me, and I think I do a pretty good job. So, all of it is weird. And it really screws with my imposter syndrome.

As someone who has taken your classes and taught with you twice, one of the reasons I think students take so well to you is because the structure of your class is a little looser. And I wonder if you think that that helps to foster creativity and the ability to tell stories. Because I’ve been in a lot of other storytelling classes that are very rigid, and I haven’t had the same results as I did in those as I did when I was taking classes with you.

Well, thank you. And I like teaching like that because that’s how things get created. Things don’t get created when you have a set of rules you have to follow because there’s no room to play, and what we do is all play. We basically lie for a living. We make shit up all the time, and people give us money. It’s a great deal. But the face of a writer is usually blank, where they’re just staring off. But they’re writing because they’re processing because you can’t just spit it out ’cause it’s not math or any science. It’s not like putting a car together. And by the way, don’t ever ask me to put a car together. It’s like technical writing.

I’ve known you for almost three years now and for the longest time I forgot about your tattoo of Groucho Marx on your upper left arm. But when I remembered the other day I wondered, what about him made you want to get that tattoo?

Groucho Marx is my hero. He is my hero because he is the funniest man that ever lived. He has a filthy, dirty mind but couches it with humor so that only the others that have dirty minds get it. Other people just think he’s funny. His timing is fucking brilliant. He was a brilliant comedian. And I grew up watching his stuff. He’s the greatest comedian that ever lived. Another reason I love him is Bugs Bunny is Groucho Marx in bunny animated form. Exact same character. Hawkeye Pierce is Bugs Bunny and Groucho combined. Like the court jester from commedia dell’arte. They were trope characters. And Groucho Marx is that kind of character. That’s why I love Groucho. And I got this tattoo on my 50th birthday because 50 was a big year of realizing that I’m halfway done at the best. It was my “fuck you” to 50 and I got this three-hour tattoo and then I went to a Bob Dylan concert. And I don’t have any other tattoos. Just Groucho. I thought about it. And, of course, my joke is I’ve thought about getting John Lennon on [the other] arm. So, I would have Marx and Lennon, and my communist friends would think I was the funniest person who ever lived.

Obviously he means the world to you because you grew up watching him. How do you think he influenced your comedic voice and the way that you create things that you really love?

Asides. Groucho Marx does comedic asides that are brilliant. Like, he’ll break the fourth wall, and I just found that fascinating when I was younger. And part of my comedy — and actually part of who I am now because I am this comedy now, I can’t take that away, I’ll do asides all the time. People will say something, and I’ll go, “Oh yeah! (But not really).” And that’s what Groucho Marx would do. He would do those funny, funny asides, and it’s kind of that wink and a nod to the audience. Like, “We’re in on this, and they’re not.”

So, in addition to your many years of screenwriting, you’ve also written several books about, in your words to me once, “stupid people doing stupid things.” What made you want to write those books? What was the driving force behind that?

Truly, truly and without joking, the driving force behind those books was money. I mean, I fell into something in the late 90s with this America’s Dumbest Criminals. It just came about when I was just having coffee with a friend of mine, and we were broke TV producers whining about how creative we were and who was gonna pay for this coffee because it’s not gonna be me. And we just came up with this idea called America’s Dumbest Criminals. The title said everything, and everyone likes to laugh at criminals. And then I wrote a book, it became a New York Times Best Seller, and I thought, “You know, this is a pretty interesting way of making money.” Because you can work from home, you can make shit up yourself. And I fell into this — well, I don’t know if I fell into this niche, or I created this niche of the type of comedy that I write that makes fun of stupid people. And it’s been very, very successful. You know, I’ve had two New York Times Best Sellers and three national bestsellers, and, like, 30 books and TV shoes based on the books. I mean, the radio people loved these stories. The morning zoos crews like Weenie and the Butt loved this kind of shit. Because they could read the stories, get a laugh, and no one’s going to be upset because they’re about criminals. So, I love writing books. It’s very romantic. I wish I was a better writer. I wish I could write stuff that was more serious and meaningful. But I don’t know if I can because I still have that imposter syndrome. I’m trying, but it’s hard for me to dig out of 20 years of writing this kind of comedy. Basically, they’re bathroom readers. And my advice is if you read more than three stories in one sitting, you should seek medical attention.

I wanted to know if writing them brought any kind of change or influence on your process when it comes to writing screenplays.

Yes, writing the books did have an effect on how I would write screenplays because I learned how to do research. The stuff I did is all historically based so I have to have two or three sources per quote because I don’t wanna lie to people. And I just became a super, duper researcher and along with researching comes the rabbit holes. And that’s how I found this guy named Pujol who was a fart guy from the Moulin Rouge. He would perform on stage in the turn of the century and his whole act was farting. He would fart sounds and music bits and dogs barking and people whining. And they loved him! He was making more than Sarah Bernhardt. He was making 20,000 francs a week at the Moulin Rouge. No one’s ever heard of this guy; I love this guy. And I wouldn’t have found him had I not, What’s that mean? What’s that mean? What’s that mean? I encourage going down rabbit holes. What gets me about writers sometimes is that they shy away from being specific because they want to speed through this screenplay and get it done. What makes things good and relatable to human beings is specific references, not generalizations. You can’t get a feeling off a generalization. Be specific, and the only way you can be specific is by doing research. Everything has a name. And I use, for example, the dinner party scene from a student who will remain anonymous. They said, “He walked into the room with a bottle in one hand and the thing that holds wine.” And I went, “You mean a … glass?? A carafe? What thing holds wine?” And I thought, fucking look it up. You’ve got everything right here on your phone. Look it up. You know, don’t be lazy and go, “Yeah, this takes place in medieval London.” And then one of the characters goes, “Hey, man! What’s happenin’?” That’s not how it works. How do they speak? What words did they use? Be specific, make it realistic, or people won’t believe it.

One of the things that has been so good for me as a writer is learning the importance of looking things up and making sure you’re being accurate. Especially when you’re writing about an experience that you’re not familiar with. Then you have to be super careful about making sure you get it right.

I’ve had students during the early parts of the class when we’re pitching ideas say, “I have this idea. It’s takes place in the 1850s in France, and it’s about a painter.” And I went, “Wow, have you ever been to France?” “No.” “Are you a painter?” “No.” “Do you know anything about the 1850s?” “No.” Then why the f — ? Write it about your father then! It doesn’t have to be some historical tome. But if it is, it has to be researched properly. And people don’t like it because it takes a lot of work. You can’t write a story from whole cloth. It has to relate to you somehow. Everyone always says, “Write what you know.” Well, you’re going to anyway. Because if you don’t know it, you can’t write about it. But I heard someone say, “Don’t write what you know. Write what you don’t want people to find out.” And I thought that was a really cool writing prompt. “What do you not want people to know about you?” That’s what they want to know about you. I won’t do it, but you should.

You have taught so many beginner screenwriters over your last four years at MTSU. I know that for me, your voice and your influence have been very meaningful to the way that I have created and allowed myself more space to embrace what I’m good at and, also, push myself out of my comfort zone. You’ve helped me a lot. So, I want to share that gift with other people and ask for someone starting out as a screenwriter, what advice would you want to give them?

Well, the most important thing in becoming a screenwriter is not writing a great script, not formatting a great script, not having a great story. It’s being persistent. Just show these people that you can write; then they’ll tell you what they want you to write. Don’t overly worry about what you’ve got. Once you get your foot in there, then you can write any fucking thing you need to. There’s an actor named William Windom and he said he went to an audition and the director said, “Can you dance?” and he said, “Yes sir, I can.” And then he left and went right to a dance studio to learn to dance because you always say yes even if you can’t do it. The most important thing I learned in the business is being persistent. Don’t be afraid to call people, don’t be afraid to write letters, don’t be afraid to go visit them. Don’t be afraid to knock on doors; don’t be afraid to beg them to watch your stuff. But you have to have something once they say, “Okay. What have you got?” And if you don’t have anything then you fuckin’ wasted everybody’s time. So, you also have to have what I call “a trunk.” And a trunk is an old expression because I’m an old guy. And it’s basically where we used to put scripts. So, you always have trunk scripts; you’ll always have something ready if they say, “Hey, I like this. What else do you have?” You have to have shit to back up your talk. No one is impressed in our business with bravado. You know, “I’m the greatest fucking writer you’ve ever seen!” “It’s like, well, you gotta prove it. So, persistence, trunk scripts, and just write all the fucking time. Even if it’s not gonna go anywhere, even if you know you’re not gonna get paid for it. Or it’s even something you don’t like. Most students won’t do that. Persistence, trunk scripts, write all the time, get into groups of other people that are like-minded. Find other writers. Serious writers. The hardest thing that one person will do, and the best thing they can do, is find people who are better writers than they are and hang out with them. It’s demeaning as fuck, but you’ll learn from them. You won’t learn from dumb people. Find people that are like-minded. They’re the ones that will spark and lift you up, give you encouragement. Other people won’t because it’s a stupid job. You’re gonna make up stuff for a living? Count cans! I was lucky my mom and dad never discouraged me from doing all of this incredibly crazy shit I did growing up. But that happens in a lot of families: Parents will knock down the dreams. Stay away from people that will do that to you. I feel like Buddha. And one more thing: Persistence, trunk scripts, write all the time, hang out with people of the same ilk, and the last one is, if you’re noticing you don’t like what you were writing, stop fucking writing it, and write something that you like. I’ve written stuff that I know no one will ever buy but I had a great time writing. And in fact, my story of that is Hunter S. Thompson, who is one of my favorite writers of all time. He created Gonzo journalism in the 60s, which is basically he put the reporter himself in the story. And he was on the campaign trail for George McGovern in 1972 and he said, “It was boring as all hell. So, when I would get off the tour bus, I would go into my hotel room, and I would start writing this crazy fucking story that made me laugh.” And it turned out to be Fear and Loathing in Las Vegas, which was his biggest hit ever! By a landslide. And he wouldn’t have written it had he not just wanted to entertain himself. Because if you make yourself laugh, it’ll make someone else laugh. It might not make everyone else laugh, and it shouldn’t. You don’t want everyone to get it. And I had a student, Max, who I love and miss very much who would say, “Well, no one’s gonna get this.” And I’d say, “Yes, someone will get this! And it’ll be someone like you.” And they’ll go, “Oh my God, no one’s ever written shit like this. I get this!” There’s so many stories that haven’t been told about experiences that other people have had too, but one’s talking about it. And those are the hardest stories to write. And have I written them? No. Just wanted to clear the air!

Haha!

Kinsey Wilson is a recent graduate of MTSU. She majored in Video and Film Production with minors in Writing and Mass Communication. She taught Screenwriting I alongside Leland Gregory at MTSU for two semesters and discovered a love for sharing her craft with beginning screenwriters just like her mentor Leland. She is a passionate screenwriter who focuses on telling stories featuring and highlighting queer people. She aspires to continue fostering her love for writing to carry her through the hardship of navigating the workforce as a young woman.