Actor-Inspired Element: Several of Tommy and Richard's interactions (the "Does this make me look fat? / No, your face does." exchange, "Fat Guy in a Little Coat", etc.) were things Chris Farley and David Spade actually did and said to each other that the writers incorporated into the film.
Actor-Shared Background: Like Tommy, Chris Farley graduated from Marquette University in Wisconsin and did sales for his father's business as his first post-graduate job. Chris also played for the Marquette Rugby team while he attended college there. Tommy is seen wearing a Marquette Rugby jacket in the film.
Character Outlives Actor: Chris Farley died in 1997, but in the 2004 romantic-comedy 50 First Dates, Dan Aykroyd plays a neuro-physician who mentions in passing that his clinic's funding is stated to come from Sandusky, Ohio, supplied by a car parts tycoon named TB Callahan. This implies that Tommy himself was/is still alive as of 2004.
DVD Commentary: The original DVD release has one by director Peter Segal.
Dyeing for Your Art: David Spade refused to let any stylist touch his hair during filming, and also avoided combing or using a hair dryer off the set to make his character look perpetually stressed.
Harpo Does Something Funny: The sales demonstration scene was largely improvised by Chris Farley. He only discovered that there was a cigarette lighter right before filming.
Hostility on the Set: According to David Spade, he and Chris Farley got into a physical altercation on the set. Thanks to the stress and exhaustion from having to commute back and forth from Toronto to New York so they could still perform on Saturday Night Live during filming, the duo began to bicker more so than usual. Things came to a head when Spade had gone out for a drink with Rob Lowe one night after Farley went to bed. The next day, Farley became very jealous and angrily repeated "How's Rob Lowe?" Spade got so fed up with Farley hounding him on the subject that he threw his Diet Coke on him, to which Farley responded by throwing Spade into a wall and down the stairs. After the fight, Spade walked off the set and refused to continue filming. In another incident that also arose due to Farley's jealousy, Farley stomped down hard on Spade's hand. The pair would sometimes go for hours without talking to each other, talk to each other through the director, etc.
Playing Against Type: Brian Dennehy usually plays criminals or other despicable sorts. In this movie, he's a lovable guy who truly cares about his employees and has a great relationship with his son.
Romance on the Set: Lorri Bagley, who played the gorgeous blonde woman who goes skinny-dipping in the motel swimming pool, ended up dating Chris Farley for a while after she was introduced to him by David Spade. However, Spade had his own romantic designs on her and was reportedly not happy about his Just Friends status.
Star-Making Role: Tommy Boy was Chris Farley's first starring role in a feature-length film, and after the film was a surprise success Farley seemed to be on the verge of becoming a big name comedic film star. While he did star in a couple of other successful comedies like Beverly Hills Ninja, his untimely death in 1997 put a premature end to what could have been a long and successful film career.
Throw It In!: While there are probably other examples, the "Does this make me look fat? / No, your face does" exchange is confirmed to have begun as an ad-lib.
Troubled Production: The plan was for Farley and Spade to quickly complete the film during their summer break from Saturday Night Live. However, because the film had several script issues, production ran past the deadline and the two were forced to commute back and forth between New York and Toronto to do both the show and the film.
Rob Lowe turned down being billed in the credits, as he didn't want to have to pay the Screen Actors Guild fees for being in the film.
Fred Wolf worked on the screenplay uncredited.
Vindicated by Cable: While the movie did okay at the box office, it was a huge hit on video. At one point, director Peter Segal claimed that it was in the top ten selling Paramount VHS releases of all time.
Tommy's name in the original script was actually "Billy." Lorne Michaels requested it be changed to avoid confusion with Billy Madison.
Director Peter Segal had every intention of deleting the scene in which Tommy and Richard triumphantly drive back to Sandusky while singing along with the radio, believing it didn't work. An editor felt the scene was at least worth finishing before making that decision, and Segal found it actually did work with audible music, so decided to keep it in. A WCHB we can be grateful didn't happen!
The character of Helen the Waiter was originally written for Roseanne Barr, but she was unavailable.
Scheduling conflicts almost forced Rob Lowe to drop out of the film. This resulted in the filmmakers holding impromptu auditions while the movie was already filming for the part of Paul Barish. Matthew McConaughey was one of the actors who auditioned. Eventually, Lowe's scheduling conflicts were resolved, and he was able to appear.
In the original script, Richard was Tommy's stepbrother with whom he had an estranged relationship. When Peter Segal came on board, he changed Richard to being a co-worker and made Tommy's stepbrother a completely separate character.
Working Title: The film was initially titled Rocky Road and kept that title for so long that the marketing team even made posters featuring it. Then it was called Billy the Third: A Midwestern. However, Lorne Michaels was also working on Billy Madison and insisted that the the film's title be changed. Other names considered included Fat Chance and XL before settling on Tommy Boy. It was shot under the title Rocky Road.
This movie made it on Roger Ebert's most hated movie list.
. Then it was called Billy the Third: A Midwestern. However, Lorne Michaels was also working on Billy Madison and insisted that the the film's title be changed. Other names considered included Fat Chance and XL before settling on Tommy Boy. It was shot under the title Rocky Road.