People Thought The Hit Would Flop

“What’s cool is people are showing it to their kids, so now there’s a whole new group of people doing impressions of Tommy Callahan on Tiktok, and they’re eight years old. That’s fun,” laughs Tommy Boy director Peter Segal as we discuss the comedy classic’s enduring appeal as it turns 30. It originally landed in theaters on Friday, March 31, 1995.

“The fact that they’re coming out with yet another release of the movie, this is the third one, they’re running out of things to put on the discs. There are only so many outtakes.”

Tommy Boy celebrates three decades of laughter by being released on 4K Ultra HD for the first time ever on Tuesday, March 25, 2025. For those who don’t know, the film stars SNL alumni Chris Farley and David Spade as Tommy Callahan and Richard Hayden, two wildly different personalities on a hellish road trip to save the Callahan family business.

‘Tommy Boy’ Became A Pop Culture Phenomenon

Tommy Boy’s influence has spread far beyond the screen, something that still surprises Segal.

“The movie was never released internationally,” the filmmaker recalls. “I was filming in Cape Town, South Africa, last year, and I saw someone wearing a Callahan t-shirt, and I thought, ‘Wow, I think that’s the furthest point from the United States that I’ve seen someone who’s seen that movie.’ People in Europe have seen it, and I don’t know how, but it seems to be getting out there.”

“The writers of Shrek told me that they had originally patterned the relationship between Donkey and Shrek after Spade and Farley in Tommy Boy, and then they hired Chris to play Shrek, and he almost completed the whole thing before he passed. That’s one group of people that were influenced. It’s fun to watch certain commercials being made, and I see references to scenes in the movie. I’m like, ‘Hey, wait a minute, I remember that.’ That’s kind of fun. Madison Avenue sees a comedic value in some of the scenes as well, so it’s great to see it. I was in Chicago recently, in a diner, and there was ‘Tommy Want Wingy’ on the menu because of that quote in the movie. There were other businesses that I don’t think are legally meant to be using the name Callahan, but things do pop up in different cities. It’s also fun to see how the movie has permeated real life.”

Because Tommy Boy was only his second movie, its success was vital to Segal, who went on to make the Adam Sandler classics 50 First Dates and Anger Management. However, while it was a box office and pop cultural hit, it kicked off in a way that no one could have predicted.

“My first movie was Naked Gun 33⅓: The Final Insult. I was so new to making movies that I didn’t know you should probably take a break in between, but I went straight into prep for this. I remember going into my office, and the TV was on,” he muses. “I had just been to the Naked Gun premiere six weeks earlier, and suddenly, on the TV, I saw my friend at the time, O. J. Simpson, being arrested by a tree, and I thought, ‘What is going on? That must be a mistake.’ I had sat next to Nicole Brown Simpson at the Naked Gun premiere, so I thought, ‘Wait a minute. What’s going on?’ That’s literally how we started Tommy Boy. It was in a cloud of insanity. The trial of the century was our kickoff party, practically.”

People Thought ‘Tommy Boy’ Was Going To Be A Flop

While Tommy Boy isn’t an SNL movie like Wayne’s World or Coneheads, despite both Spade and Farley being alumni of the iconic show, it’s often considered part of the extended family. It was also produced by Lorne Michaels, but even that didn’t convince people that Tommy Boy was going to work.

“Lorne has had a knack for finding talent. Saturday Night Live is almost like a factory,” Segal says. “The funniest and most talented people in comedy have usually gone through those doors. The danger for us was that we were an original story from SNL. We weren’t basing anything off of a sketch, and at the time that we made Tommy Boy, the ratings for SNL were not good, yet they probably had one of the greatest casts with not just Farley and Spade, but also Adam Sandler, Chris Rock, Mike Myers, etc. but it was a dark time for the show itself.”

“There were a lot of naysayers and people who did not think we would be successful. I remember driving with Farley one day to meet Brian Dennehy for dinner, and he said, ‘Pete, everyone thinks we’re going to fail. The only way to have a victory is with a success.’ I looked at him at that point as we were driving, and it kind of felt like, and I know this might sound corny to say, but we were a Band of Brothers. We were in this together to try to pull this out because he was right. There were a lot of doubters.” Tommy Boy grossed $32.7 million at the domestic box office but went on to be one of Paramount’s biggest sellers on video.

Aside from the performances and a script that continues to be quoted today, Tommy Boy’s soundtrack and music-led classic moments have become part of the zeitgeist. It’s now public record that inclusion in the film actually gave even internationally known artists a boost.

“All those songs and sequences were written into the script. Spade had the idea for the Carpenters song,” Segal reveals. “There was a book about The Carpenters recently, and they wrote a chapter on how Tommy Boy reignited their fandom. Obviously, they were huge and iconic, but they benefited from the refreshing of their song Superstar in this movie. It was the same with Come On Eileen. That was from a group called Dexy’s Midnight Runners, and that was their only big hit. Eres Tú was a song that I remembered listening to in high school on the bus, so there were particular songs for specific moments.”

Thirty years on, despite all the hurdles, curveballs, and doubters, Segal wouldn’t change a thing about his Tommy Boy journey, but he’s looking back through rose-tinted glasses.

“It was pretty much absolute chaos. It was definitely the hardest movie of my entire career to make,” the director concludes with a nervous laugh. “I don’t recommend anyone start filming a movie without a complete screenplay. That’s a no-no. However, there is so much love for the film that obviously, I have put to bed a lot of the unpleasantness of the fear.”

“The guys were great. Everyone got along. It wasn’t like a tense set. It was just we were desperate for material. The benefit of splitting time with the SNL season was that as the guys would go back to New York, it gave me and Fred time to write a couple of extra days, Monday and Tuesday, because they wouldn’t show up for Tommy Boy until Wednesday, Thursday, Friday, or sometimes it would change depending on rehearsal schedule. It was not easy, but it was a lot of fun.”