Jamie Kennedy Started His Career As A Stand-Up, But Then His Success As An Actor Got In The Way

Jamie Kennedy started in showbiz in the late ’80s, trying to forge a career as an actor while also getting his feet wet as a stand-up comedian. While he started to make headway on both fronts, the acting gigs started coming regularly enough that he was forced to put stand-up on the sidelines for a time. Eventually, however, Kennedy was able to shift gears enough to get back in front of audiences and start telling jokes again, which soon led to comedy specials. His latest special, Stoopid Smart, debuted on Tubi over the course of Memorial Day Weekend, and Kennedy took some time to talk to Decider about his stand-up career, his comedy-writing regimen, how long it takes him to give up on a joke that isn’t working, and what it was like to work on such wildly divergent projects as Romeo & Juliet, Scream, Bowfinger, and The Jamie Kennedy Experiment.

DECIDER: First of all, I enjoyed the fact that your new stand-up special is self-deprecating from the get-go, with your introduction calling you out as “the star of Tremors 6.”

JAMIE KENNEDY: [Laughs.] Thank you, man. I appreciate it. I mean, I love my movies, but it’s real: people don’t even know sometimes that there’s a couple of other Tremors beyond the first one. But they’re out there, and they have a robust fanbase of people who really like them. But mainstream people may not know about them.

I know you’ve been doing stand-up for many years now, but what I don’t know is what led you to turn down that path in the first place.

Well, I’ve always done it. I started out as a stand-up and an actor. I just got more known as an actor. But I was making inroads to both. Probably a little bit more inroads as an actor, but I did a couple of spots as a stand-up on TV. And then I got a guest spot on a couple of shows as an actor, and that led to more stuff, and then once I got my first movie, I got busy in that for awhile. So I put stand-up on hold until the late ’90s, and then I became more of a name and started building up my headlining act from there. But I’ve been doing it for more than 20 years.

I knew it wasn’t just recently, because you put out an album in the 2000s. (Unwashed).

Yeah, I had that one, and then I had another one in 2010 (Uncomfortable), and then I made the [documentary] Heckler. But stand-up right now, there’s so many outlets to put it up, so if you have the time and you have the material and you can put it out there, you might as well do it. It’s a robust time for the art form.

So what’s your writing regimen? Or do you actually have one?

Well, it usually starts out as an idea, something I really like or that I’m passionate about or I’m thinking about, and then you go onstage and try it at the club at a little later. And then you add on and you try it again, and then you add on a little more, and then boom! And you might still riff off of that. Something might come out of your head, and you’ll use that. It’s kind of a trial-and-error process when you start. I have a buddy who I collaborate with, and he kind of helps me structure stuff. It’s a good way to do it.

Are you one of those comedians who carries a notebook with him at all times, so you can scribble down an idea whenever it hits you?

Well, I usually use my phone. [Laughs.] But I definitely write things down on paper a lot and go, “Oh, that’s funny. That’s a bit.” Because you can think of something and send yourself an email, but then the email goes away. It helps to have something constant in front of you that reminds you of that idea.

By the way, we’re almost the same age, but I just felt a whole lot older right then. It’s not like I’ve carried an actual notebook around with me done that in years. But it’s still my default mindset.

[Laughs.] Yeah, right? But it’s something that we all did!

So when it comes to working through your jokes onstage, do you ever hit one that you were just convinced was going to kill, only to have to eventually give up on it?

Often. [Laughs.] Some people will give a joke twice, some people give a joke five times, and if it still doesn’t work, it’s out. But to me… I get mad. I’m, like, “How do you not get this idea? What am I not doing here that you’re not grasping the concept?” Sometimes I’ll blame myself. I’ll be, like, “I’ve got to deliver it better or think about how to execute it more…” There are sometimes where you just can’t get through to an audience, and that’s frustrating. But you give it a good amount of time before you set it aside.

How did you hook up with Tubi for the special?

They’re a new app – they were just acquired by Fox, actually – and I think they’re great. A lot of younger people use it. Netflix is awesome, but they’re so crowded, and Tubi is robust and hungry for content, and they have some of my other specials on there and some of my movies. And they were, like, “Your movies are doing really well here. Why don’t you put your special on here?” And I said, “Okay!” I think they’re gonna be the next big thing…and they’re on their way!

Speaking of your films, I wanted to ask you about a few other things in your back catalog. First of all, I know IMDb says you’re an uncredited extra in Dead Poets Society, but…is that actually true?

It is true.

Okay, I knew you’d had a burgeoning career as an extra, but I didn’t know if that was actually one of the films.

Yeah, I was lucky. it was the first thing I was ever in, and it was three days. It was just a bizarre, surreal time. It was just mesmerizing.

Who did you actually get to interact with?

I had some interaction with Josh Charles, and a lot with the dudes that were in and around his crew, like that red-haired kid (Allelon Ruggiero) and another kid. Robert Sean Leonard wasn’t really there a lot. He was very serious about it, and that’s the way he should’ve been. But Josh Charles, he was pretty chill. And I was around Ethan Hawke in a scene where it was him and his dad. That was pretty intense watching that, knowing what that scene was about.

I’ve got your book, Wannabe: A Hollywood Experiment, and I remember you talking about having to work at Red Lobster at one point to make ends meet. Was there any point during that era where you thought about just giving it up?

Multiple times! I didn’t really have a lot going on for a few years, and I was just, like, “I don’t know what I’m gonna do, I’m not making money, and I don’t know how it’s gonna happen.” But I was obsessed. And I think that’s how you do it. You can’t walk away. People who do what we do, I think that’s what you need. You’re not gonna stop. But I don’t care who you are, just because you do have some success, it doesn’t mean you get to keep it. But there was nothing else I wanted to do, there was nothing else better, and I didn’t have anything to fall back on. So I just kept my eyes on the prize.

Scream was the big game-changer, but I know you’d done a few sitcoms before that.

Yeah, I’d done a few guest spots. Ellen [DeGeneres] was very nice to me. I did her show, and she had me on a couple of times, and that led to other guest spots. Just being able to get paid and get a nice check, make your monthly nut in a week, and then you’d have, like, three more weeks to get a job. But you get that first check, and you’re, like, “Oh, this is gonna float me for another three weeks. Yes!” And then you’re hustling every day to figure that out, and then it starts floating into residuals, and you go, “Oh, that’ll float me for the next six months!” It’s all about the building blocks.

I’d completely forgotten that you were in Romeo & Juliet.

Yeah, I had a good little role in that.

It must’ve been a pretty big deal for you.

It was, because I’d only done TV, and only little spots here and there. But I was working my way up, so that was just amazing to be in a movie that was such a piece of art. That role has always left a mark.

Since he just passed away, I have to ask what you remember about working with Brian Dennehy.

You know, I really didn’t have much with him. I just remember seeing him on the set one day. I didn’t really interact with him. I just remember how intense he was and thinking, “This guy… He has an intense energy about him.” He was all about business. Because, you know, he’d been around a long time. But he was a great actor.

Was DiCaprio pretty cool?

Oh, yeah. I mean, he was burgeoning into the supernova that he is. He was just a dude that was loving acting. That’s what I always remember. He was just loving it, how great it was, and how cool it was to be doing this stuff. He was a fun guy.

And then came Scream, which presumably involved a fair amount of auditioning.

Tons of auditioning for that. I had to go for it three times, then I had to do screen tests, and…it was a lot. But, you know, I didn’t really have any credits. But thankfully, Wes Craven believed in me. To this day, I owe him my career.

Yeah, I’d read that he pushed for you because, credits or no credits, you were the best one for the role.

Yeah, that’s Wes. Wes always wanted to pick the people he felt fit the role the best and had the right energy. I mean, look, he broke Robert Englund, gave starts to Johnny Depp, Rose McGowan, myself… [Laughs.] He broke a lot of great people, and I’m lucky to be on that list of people that he gave early jobs to.

You were also in a film around that time which didn’t really do anything at the box office but which I really liked: Clockwatchers.

Oh, yeah, Clockwatchers I got after I finished Scream, and that was really my first true indie. And it was so cool, because it was Parker Posey, Lisa Kudrow, Toni Collette, and Alana Ubach, these four girls in an office, and I was the office boy. It was a mid-’90s Sundance type of movie, and…it was just fun, man, being on the set with all those woman, those powerhouses. I was like their little brother. [Laughs.] They were great. I had such a good time.

And you got to work with James L. Brooks on As Good As It Gets.

Yeah, he’s another one who’s a great dude that totally just knows what he wants. And he tries things. All the great ones try different things. He’ll try a scene five different ways and then go, “All right, I’ll see what I have in editing.” And that’s what I love. I love working with people like him and that, because they’re very honest with you. “I liked that one, I didn’t like this one, let’s try this one again.” And he was the king of that.

Bowfinger is one of those great underrated comedies, but most comedy nerds swear by it.

Bowfinger is just amazing. Working with auteurs like Steve [Martin] and Frank [Oz] and Eddie [Murphy]… Steve wrote it and starred in it, and he knew what he wanted. I played his sidekick. And just getting to work with guys like that… It was like being able to go to school, I learned so much from it at the knee of greatness.

The idea of putting Martin and Murphy in the same film seemed odd at the time, just because their styles are so disparate, but they found a way to make it work.

Well, they’re both icons, you know? Steve was the first comedic rock star in the ’70s, Eddie was the first comedic rock star of the ’80s, and they were just beautiful together. Different energies, mutual respect. And I was at comedy school every day. It was just awesome.

I know you’re scheduled within an inch of your life today, but before we go, I just wanted to ask about the experience of getting to do The Jamie Kennedy Experiment.

The Jamie Kennedy Experiment was just a way for me to… I mean, people liked me in movies, and I got to be funny in movies, but I was reading other people’s scripts and saying their lines. And it was great, but The Jamie Kennedy Experiment was my first crack at trying to do my humor and something that I could create and have a hand in. And that was a new type of school, except this time it like was a third-grader throwing things against the wall to see what stuck. [Laughs.] But it was a beautiful, wonderful, creative, crazy time in my life, and I’ll never, ever forget it. It was just a great time.

Will Harris (@NonStopPop) has a longstanding history of doing long-form interviews with random pop culture figures for the A.V. Club, Vulture, and a variety of other outlets, including Variety. He’s currently working on a book with David Zucker, Jim Abrahams, and Jerry Zucker. (And don’t call him Shirley.)

Watch Jamie Kennedy: Stoopid Smart on Tubi