Dave Chappelle’s advice to ‘Entourage’ star Jeremy Piven aided his jump to stand up
Having been in “the game” since 1986, actor Jeremy Piven is well acquainted with the unintended skill of “bombing,” when a project he’s poured himself into is greeted with a yawn from an audience, or series of well-placed spears from critics.
Bombing on TV or film offers a thin veil of protection. Bombing on stage, in front of a live audience, offers no such barricades, or escape routes. It is an element that a live performer must not only accept, but lean into.
“The thing about bombing on stage is, and Dave Chappelle told me this, ‘You have to bomb but you have to bomb at the right time.’ I believe that,” Piven said in a phone interview. “You have to put yourself in situations that are very difficult.
“Like, at a dive bar, and they’re waiting to hear the DJ. Or the audience doesn’t know who you are. And you’ve got the comics in the back who want you off so they can do their set. It’s hostile. Your whole body is telling you to get off stage. And you know it right away.
“In a TV or a film, there are so many people involved and so many variables that you don’t get tied to the outcome or results. I get it, everyone is looking at the scoreboard.”’
Piven’s scoreboard started with a small role in the 1986 film, “Lucas.” It’s 2025, and his IMDB scoreboard is loaded with credits of all shapes, most notably his role as the obnoxious agent Ari Gold in the hit HBO series, “Entourage,” which concluded in 2011.
Piven has a new film coming out at the end of February, “The Performance.” It’s based on a short story penned by Arthur Miller; it’s the story of a Jewish tap dancer who is scheduled to perform in 1930’s Berlin, before Adolf Hitler.
Before the movie is released, Piven will continue to do what he took up several years ago. He is now a stand up comedian, and he is scheduled to perform on Feb. 7 and 8 at the Arlington Improv.
He talked to the Star-Telegram about this new career phase, losing his mother, and working with Robert DeNiro.
Star-Telegram: What led you to the stand up route?
Jeremy Piven: I have been lucky enough to be on stage since I was a child. I did film and TV, and the one lane I hadn’t done is stand up. I had dabbled in it. It is fascinating to me.
I did Second City in Chicago with (the late) Chris Farley. I am an improviser. I really had never had put it all together. It terrified me. If you lean into that fear, if you are OK being humiliated in public, which happens, you can really grow and do things that you haven’t done. Stand up enhances my acting.
Star-Telegram: Is stand up harder than you thought?
Jeremy Piven: It’s harder than you can even imagine. Initially it’s terrifying. I’ve been touring over a decade now and I do love it. I put myself in all types of different situations. And I found a new lane that’s tougher than that - speaking at your mother’s funeral.
(Piven’s mother, Joyce, died on Jan. 19 at the age of 94. She was a towering figure in the theater community.)
S-T: You mentioned that you lost her on social media; was speaking at her service cathartic for you?
JP: I’ve been preparing for that like it wasn’t going to happen. We’re good at fooling ourselves, I guess. Being able to navigate that space, ‘doing a tight 10 minutes’ at your mom’s funeral, how do I speak truthfully and honor her? To find the duality of life is what she did. She instilled that in me, and she was my acting tutor.
There is no difference between drama and comedy. They can live simultaneously. She had a rule that you could say whatever you want, as long as it’s funny. Endings are important, and she was right and the way she ended was graceful.
I would read lines to her from ‘Entourage’ and people couldn’t believe it because Ari was such a loud mouth douche bag. But I could unpack that with her and she understood because it’s fiction, and it’s just dialogue.
I am not Ari Gold, but I can unpack that and (being on stage) is very cathartic for me. I’m very lucky. I have this lane now that I can go to and open up, and make people laugh.
S-T: Your parents were both theater people so they understood the business; did they try to persuade you not to do it as a profession?
JP: No, but more important is that they didn’t try to talk me into it. They put me on stage when I was 8. Someone said to me years ago that they were mad at me because ‘acting comes way too easily’ for me. I said, ‘Thank you. I’m half-a-century overnight sensation.’ If doing it and always performing comes easily, I don’t know if that’s easy.
I know the harder you work the easier it looks. My parents threw me on stage, and they would always say, ‘You’re enough.’
S-T: The ‘You’re Enough’ line is a common phrase, how long did it take before you believed it?
JP: When you’re that young, you’re being taught, being on stage and getting out of your own way and being present. (His parents) had theater games to do it, and to be the authentic self. That’s the highest vibration.
You’re a kid on stage, and you’re doing improv’, and you’re butchering Chekhov, I didn’t think there was anything unique about it. I thought every kid does this. I was just logging hours on stage.
When I got to college, I played Marc Antony at Drake University in Julius Caesar, and my parents saw me and said that I should do this for a living.
S-T: In entertainment interviews, actors or directors or musicians are often asked, ‘Did you know such and such was going to be a hit when you made it?’ Does anyone ever really know that?
JP: I will say I did feel that with Entourage; given the subject matter, I knew pop culture, and that people were fascinated of the backstage life of Hollywood. We were on mainstream TV, in a good place on HBO, and we were allowed to swear; we had the freedom of language.
S-T: You had a small part in the action movie “Heat,” where you are forced to give Robert DeNiro the shirt off your back. Was doing that intimidating?
JP: Of course it is. We all grew up watching DeNiro. He is the high water mark for any actor; he’s been a part of those performances; ‘Raging Bull,’ ‘Taxi Driver,’ and there he is. But at the same time, and this was before ‘Entourage,’ I was maybe 30, or something.
I had been studying for 22 years. You breathe through it. You can look at it and be overwhelmed by it, and disappear, or you enjoy that you get to post up against Michael Jordan and give him everything you’ve got. It’s possible, and I am dumb enough to think I can do it.
I waited many hours in that waiting room (for the audition) to deliver my two or three lines. I stuck it out. Lot of guys didn’t. I knew if I stuck it out, I knew I had a chance to do a scene with DeNiro. I remember when I did it, (Heat director Michael Mann) said in this deep Chicago accent, ‘That was great! Do it again! Do it again! I gotta call Bob!’ He wanted to make sure it was OK.
Even with this teeny, tiny role you have to jump through hoops and hoops. On the day I (shot the scene), I improvised. You have to be a scrapper, and you take the little roles and make a meal out of it. I was in there with DeNiro swinging away, and the roles expand. But it works. Yes, I was scared but I knew you have to embrace that fear.
S-T: The last time I interviewed you was in 2009, and I asked you if you could play any part, what would you pick. Do you remember the part?
JP: Was it Lenny Bruce?
S-T: It was Harry Houdini.
JP: Oh, that’s a good one. If you talked to me back then, 15 years ago, that was right at the time I bought, ‘The Performance.’ So I said Houdini, and what I should have said was Harold Man in ‘The Performance.’
S-T: Thanks for your time and best of luck with your stand up show, and the new movie.
JP: Thank you very much. Please come out and see us, and hit me back when the movie comes out.
