7 Times Ben & Jerry Stiller Proved They Were Hollywood's Funniest Father-Son Duo'

It was only natural that Ben Stiller would be one of the funniest people in Hollywood, given that his parents, Jerry Stiller and Anne Meara, were one of the most successful comedy duos of all time. While there are many celebs you didn't know were related, Ben is undeniably descended from comedic royalty. His inherited talent often manifested in the on-screen dynamic with his father whenever they would appear together in interviews or films, bouncing off each other like ping pong balls. Jerry could be counted on to go bigger, seeming to overbear his son, while Ben maintained a quieter, more straight man response that perfectly balanced the comedy equation and led to major laughs. They starred in several films together, often with Ben directing, including both of the "Zoolander" films, as well as other projects like "Heavyweights" and "The Heartbreak Kid." There were also some priceless talk show moments, like when the whole family played charades on "Late Night with Jimmy Fallon."

Both father and son had high praise for each other's comedic skills. "Ben was ahead of me, in a lot of ways," Jerry told The New Yorker in 2012. "Everything I could never do, Ben could do." Ben made a similar comment about his father shortly after Jerry passed away. "And it's, like, my dad is so funny. Like, I've never, ever thought I was funny like my dad. Or as funny as my dad. I've never really felt a competition, because I would lose, hands down," said Ben to the The New Yorker in 2020. Read on for the funniest moments from the father-son duo working (and laughing) together.

In 1996, Ben Stiller was doing the press rounds to promote his second directorial effort, "The Cable Guy," starring Jim Carrey and Matthew Broderick. Ben appeared on "Late Night with Conan O'Brien" to talk about the film, and his father, Jerry Stiller, accompanied his son in the interview. Initially, Jerry came out to explain that Ben had been ill and couldn't make it to the interview, pretending to be embarrassed by Ben's absence. "This is the way you treat a guy like me at this point in my life?" Jerry asks after lamenting he gave Ben everything. He storms off stage to find Anne Meara, Jerry's wife and Ben's mother, pretending to baby Ben in a dressing room.

Jerry then drags Ben onto the set and they do the interview about "The Cable Guy" together, with Jerry routinely interrupting Ben. He instructs Ben on how to properly tell a joke, in a fashion that was almost nothing like their real life dynamic. Ben initially resisted his dad's help in his overall career but ultimately welcomed his support, especially for awkward publicity events and awards show gigs. (You my recall how Ben's 2021 Golden Globes bit didn't quite go as planned.) "I was looking at some old clips of the two of us on 'Conan' ... And I'm remembering that of course I wanted my dad on there with me, because I knew my dad would be funny. And I would dread the talk-show appearances, and it was like cheating to ask him to come and help," Ben told The New Yorker.

Jerry Stiller had a career resurgence when he joined the cast of "Seinfeld" as George Costanza's dad, Frank Costanza. He then went on to play the father of Leah Remini's character on "The King of Queens," Arthur Spooner. Similar to Frank Costanza, Arthur was loud and pushy but undeniably hilarious, often clashing with Kevin James' character, Doug Heffernan. Jerry appeared on all nine seasons of the show, with his character getting a fitting ending in the show's final episode when he married Veronica Olchen, who was played by his real-life wife, Anne Meara.

In a Season 4 episode titled "Shrink Wrap," Arthur goes to therapy and has flashbacks to his own father, played by Ben Stiller. It's hilarious to watch Ben channel a tough guy version of his dad, and even funnier to watch Jerry interact with him during the memory as they argue about Arthur's older brother. Even in memory form, Arthur is intimidated by his dad, as is his therapist, played by William Hurt.

In "The Heartbreak Kid," Ben Stiller plays Eddie Cantrow, a lonely singleton who abruptly marries a woman named Lila (Malin Akerman) only to discover her myriad flaws and red flags. Eddie then falls for another woman while on his honeymoon with Lila. Miranda, the woman Eddie falls in love with, was played by Michelle Monaghan, who you may recognize from the cast of "White Lotus" Season 3. Complementing the star-studded cast is Jerry Stiller, who plays Eddie's dad, a rather sleazy and dirty old man by the name of Doc. In a memorable clip, Doc urges his son to get with more women, asking Eddie if he's "crushing" any ladies (to put it mildly).

It's a hilarious part for Jerry, channeling a cruder version of Frank Costanza alongside his more milquetoast son on-screen. Still, Doc is supportive of Eddie, as seen in the movie's finale when Ben tries to confess his feelings to the woman he really loves. Doc's ready to physically fight for his kid, despite being well into his 70s!

Ben Stiller's parents, Jerry Stiller and Anne Meara, were one of the most famous comedy duos of the midcentury, making hundreds of talk show appearances as they riffed off one other. Fans of Ben were treated to a sample of this hilarious dynamic when the family appeared together on "Late Night with Jimmy Fallon" in 2010 for a game of charades. Ben teamed up with Fallon, while Jerry and Anne worked together and flexed their comedy skills.

It's easy to see why they worked so well together and how Ben got his sense of humor from his parents but made it his own. Jerry and Anne both talk through their attempts at the game, cracking up Fallon, Ben, and the audience. The older couple may have technically lost the game of charades, but they won over viewers. "They were very different people, but they were so, so devoted to each other," Ben later noted to The New Yorker. "A very beautiful and imperfect relationship, as every relationship is. And so that was our life. And it was part of all of it for us."

Jerry Stiller and Anne Meara were one of many actors and actresses who we lost in 2020. After the deaths of his parents, Ben Stiller began working on a documentary looking back at their comedic legacy and private family life. The result was 2025's "Stiller & Meara: Nothing is Lost," a touching tribute to Jerry Stiller and Anne Meara, including their impact on him and the entertainment world. Ben worked on the documentary for years, combing through mountains of material, including recordings and home videos made by his dad.

"My dad recorded so much," Ben explained on "Jimmy Kimmel Live!" in 2022, adding that he wouldn't always tell the family when he was recording. That led to a hilarious moment when Ben was in elementary school and wanted to walk to school by himself for the first time. Jerry, being "overprotective," decided to keep an eye on him. "He followed me in a car and shot footage of me walking to school on my own." Ben added, "A cop stopped him [Jerry Stiller] and said 'Why are you filming that child?'" The story was a great precursor to what the documentary ended up being, an intimate look at a show business family that stayed grounded in spite of incredible success.

In "Zoolander", Ben Stiller starred as the memorable male model Derek Zoolander, alongside Owen Wilson. The "Zoolander" films feature many famous celebs in disguise, including David Bowie, Billy Zane, and even Ben's parents. Derek may not have had a supportive father, but Ben's real-life dad was happy to appear in his son's film. Ben directed both "Zoolander" and "Zoolander 2," casting Jerry Stiller as Derek's manager, Maury Ballstein. Maury was a familiar Jerry Stiller-type character, a show business vet who took no nonsense and defended his dippy male model client to the end.

In 2012, Jerry admitted he had been hesitant to be in the film. "Ben was acting with me, and also directing me — 'Do it this way, Dad. No, this way.' He wanted perfection, and I was getting a little huffy. I didn't even want to be in the movie," Jerry told The New Yorker. His wife, Anne Meara, interjected, "Jerry was afraid people would think he was riding on his son's coattails," to which Jerry replied, "Yeah, something like that."

Ben Stiller starred in the '90s children's comedy "Heavyweights" as Tony Perkis, a fitness guru and maniac who takes over ownership of a summer camp for overweight teens. The previous owners, who were much kinder people, were played by Ben's parents, Anne Meara and Jerry Stiller. Their appearance in the film is brief but memorable, as they sweetly but regretfully inform the kids they have to give up the camp due to financial mishaps. After sharing the news of his departure, Jerry's character imparts some memorable advice to the kids: "Never let anyone sign your checks!" That's when Ben's overly intense Tony Perkis enters the scene and promises (aka threatens) to shake up the once peaceful camp.

Ben's performance as Tony Perkis is a memorable one, as well as a clear inspiration for his later character of White Goodman in "Dodgeball" less than a decade later. "Heavyweights" also allowed Ben to channel some of his dad's energy near the end of the film when he appears as Tony Perkis Sr., who swoops in to remove his crazed son and eventually return the camp to the counselors who cared for the kids. There's a little of Jerry in Ben's performance as the older character, and it's an amusing glimpse at some of their future work together.