Ben Stiller Talks Bob Saget, the ‘Cable Guy’ Super Bowl Commercial, and Which Oscar-Winning Movie He Regrets Not Directing

Hollywood superstar Ben Stiller returned to the Stern Show Wednesday to discuss his new series “Severance” and delight listeners with a handful of hilarious anecdotes about everything from show business and his famous parents to the film pitch he failed to land with the Rolling Stones. Though the 56-year-old entertainer has written and directed projects all throughout his career, he remains best known for starring in blockbuster movies like “There’s Something About Mary,” “Zoolander,” and the “Night at the Museum” franchise. In recent years, however, the multi-hyphenate has spent considerably more time working behind the camera than in front of it. His directing and producing efforts have paid off, too. Ben scored two Emmy nominations for his work on the 2018 miniseries “Escape at Dannemora,” starring Patricia Arquette, Benicio del Toro, and Paul Dano. Now, he has re-teamed with Arquette on Apple TV+’s critically acclaimed new sci-fi thriller “Severance,” which Stiller both executive produces and directs.

“It was a script written by a writer named Dan Erickson who submitted it to our production company five-plus years ago as a writing sample,” Ben told Howard. “I read it and [we] thought, ‘This is great … Can we make this?’”

He told Howard plenty of scripts have landed at his feet over the decades. While he’s turned some, like “Severance,” into films and TV shows, a few other great projects managed to get away.

“I’ve passed on things I have regretted for sure,” Ben said.

“Like what?” Howard asked.

“Directing ‘Good Will Hunting,’” Stiller responded.

Gus Van Sant went on to direct the Robin Williams, Matt Damon, and Ben Affleck drama which not only became Damon and Affleck’s breakthrough acting roles but also earned the then-unknown duo an Oscar for their script.

“I got sent it by my agent at the time. The first turn off was that these two guys were attached to it to act in it who wrote it. I was like, ‘What? Come on. I cast my own projects. Who are these guys?’” Ben recalled with a laugh. “So that was one that I was like, ‘Uh, I missed the boat.’”

While Stiller regrets passing on “Good Will Hunting,” he acknowledged some collaborations just aren’t meant to be. “Sometimes it’s [about] where you are in your life at that point. You go, ‘Okay, that was good, but I really couldn’t do it at that time,’” he concluded.

Remembering Bob Saget

TV icon and legendary funnyman Bob Saget left the comedy world reeling when he passed away tragically in January at the age of 65. On Wednesday, Stiller didn’t shy away from talking about how much he revered Saget.

“He was such a sweet person. I didn’t know him well, but over the years he would always reach out … He was such a warm person,” Ben said, adding, “He just always put out such positive energy and was really, really funny.”

Stiller told Howard he regretted passing up a recent opportunity to join the comedian’s podcast, Bob Saget’s Here for You. “I felt awful. I was supposed to do his friggin’ podcast, and I didn’t do it,” he said, explaining that he meant to but kept putting it off. “I’ve said yes to 30 podcasts now. People I don’t even know,” he added with a laugh.

Ben wasn’t the only member of his family who shared a connection with Saget. His late mother, actress and comedian Anne Meara, befriended Bob after working with him on a TV movie.

“My mom loved him,” Stiller said. “I think they both had this sort of really wicked sense of humor—[they] were not afraid to go there and be dirty—and she just really appreciated him and loved him.”

An Unlikely Cult Classic

Over 25 years since its release, “The Cable Guy,” a Stiller-directed comedy about the bizarre yet hilarious relationship between an ordinary guy (Matthew Broderick) and his off-the-wall cable TV technician (Jim Carrey), has cemented itself as a cult classic. It’s become so beloved with time that Carrey reprised the role earlier this month in a Super Bowl spot for Verizon. As Howard noted, however, the film wasn’t exactly a box-office hit when it opened in theaters back in 1996.

“That’s putting it mildly,” Ben agreed. “It tanked. It was reviled.”

Happy though Stiller was to learn “The Cable Guy” had grown so popular, he hardly saw the commercial for the big game coming. “It was surprising to me,” he said. “I think most young people watching were like, ‘What the hell was this? So what?’ When we did it, people sort of had the same reaction the first time.”

Regardless of its critical and theatrical reception, Ben told Howard he only had fond memories of shooting “The Cable Guy” with Broderick and Carrey. “We laughed so much making the movie. [It] was one of the most fun experiences I’ve ever had,” he said.

A Failed Attempt to ‘Start It Up’ With the Rolling Stones

Ben corroborated and elaborated on the story director Judd Apatow told the Stern Show back in 2015 of a potential collaboration with the Rolling Stones that would have seen Stiller starring as one of the band’s superfans along with a relatively unknown Brad Pitt. And though frontman Mick Jagger initially approached them about the hybrid concert film idea, it came with one big catch. “We had to pitch the Rolling Stones,” Ben revealed. “Mick got us on board but then was like, ‘You’ve got to get everybody else on board.’”

That call led to the duo visiting the Stones in Toronto as they rehearsed for an upcoming tour. Ben recalled the meeting being overwhelming. “They were all sitting there, kind of huddled around and … I was trying to tell them how funny it would be,” he said after admitting pitching wasn’t necessarily his strong suit. “Even the idea of like comedy and rock and roll … The idea probably wouldn’t have worked, you know, in execution because people would have just wanted to see a Rolling Stones concert film.”

That’s not to say Ben doesn’t respect Jagger as an auteur. “He’s a real film guy … he’s an actor,” he said of the Stones singer. “Who knows, maybe it would have worked.”

The Time Jerry Stiller Lost His Cool

Ben also shared a story involving his other famous parent, Jerry Stiller, who passed away in 2020. The comedian, author, and beloved “Seinfeld” regular had long been known as one of the kindest guys in the industry, but that apparently didn’t stop him from once snapping at actor and director Charles Grodin.

“[Grodin] told me that once he was directing my dad in a play on Broadway, and he gave my dad some note,” Stiller recounted. “He said my dad looked at him and said, ‘When somebody talks to me like that, it makes me want to punch them in the face.’”

Ben said hearing the story blew his mind. “I never ever imagined my dad [doing that], but he had this deep, deep anger within him and rage that he suppressed underneath the sweetness … which eventually came out in his ‘Seinfeld’ character,” he said.

“That’s a funny story,” Howard responded before asking Ben, an accomplished director himself, if any actors have ever gotten up in his face.

Ben did recall one actor “testing” him on set. “It forced me to have to deal with my own issues of being confrontational,” he told Howard. “What I said to this actor was ‘When you do that it scares me, and I don’t want to be scared when I come to the set.’”

His speech to the unnamed actor apparently worked. “It ended up being, in retrospect, a really great working relationship,” Ben said. “In the moment, it was like, ‘This is the hardest thing ever.’ A year later, I was like, ‘Well, look what we got out of it.’”

Courtside With Pete Davidson and Jon Stewart

Cameras recently caught Ben Stiller sitting courtside at a New York Knicks game with fellow Stern Show vets Pete Davidson and Jon Stewart. Though he lamented not wearing a mask to the basketball game—and told Howard he later came down with a mild case of COVID—Ben had only nice things to say about hanging with Stewart, the former “Daily Show” host, and Davidson, a renowned ladies’ man and star of “Saturday Night Live.”

“Pete is having a moment in time right now. He’s an incredibly sweet guy … He’s so personable. He’s got such a charisma, and he’s funny—really, really funny,” Ben said. “I get the sense that he’s a guy who really loves to work and cares about his work, and I think that’s how he’s going to be known. He’s got a lot of great work ahead of him, too.”

Howard and Ben both marveled at how Pete has been able to mine so many laughs out of essentially just playing himself on “SNL’s” “Weekend Update” segment.

“I think that’s why he became popular,” Stiller concluded. “He really has a real charm about him.”

“Severance” is streaming now on Apple TV+.