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2* ActorInspiredElement: 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 Creator/ChrisFarley and Creator/DavidSpade actually did and said to each other that the writers incorporated into the film.
3* ActorSharedBackground: Like Tommy, Creator/ChrisFarley 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.
4* CharacterOutlivesActor: Creator/ChrisFarley died in 1997, but in the 2004 romantic-comedy ''Film/FiftyFirstDates'', Creator/DanAykroyd 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.
5* DawsonCasting: Creator/ChrisFarley, Creator/DavidSpade, and Creator/JulieWarner were in their late-twenties/early-thirties playing Tommy, Richard, and Michelle, all of whom are supposed to be in their mid-twenties.
6* DVDCommentary: The original DVD release has one by director Peter Segal.
7* DyeingForYourArt: Creator/DavidSpade 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.
8* EnforcedMethodActing: Creator/DavidSpade and Creator/ChrisFarley were real-life VitriolicBestBuds, right up until Farley's passing, but because of numerous tensions (see HostilityOnTheSet), they ''really were'' driving each other nuts during the making of this film.
9* FakeAmerican: Creator/DanAykroyd, who is Ontarian by birth, takes a Superfans-esque Chicago accent in playing Zalinsky.
10** ActorAllusion: [[Film/TheBluesBrothers Not the first time he's put on a convincing Chicago accent]].
11* HarpoDoesSomethingFunny: The sales demonstration scene was largely improvised by Creator/ChrisFarley. He only discovered that there was a cigarette lighter right before filming.
12* HostilityOnTheSet: According to Creator/DavidSpade, he and Creator/ChrisFarley 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 ''Series/SaturdayNightLive'' 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 Creator/RobLowe 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.
13* PlayingAgainstType: Creator/BrianDennehy 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.
14* RomanceOnTheSet: Lorri Bagley, who played the gorgeous blonde woman who goes skinny-dipping in the motel swimming pool, ended up dating Creator/ChrisFarley for a while after she was introduced to him by Creator/DavidSpade. However, Spade had his own romantic designs on her and was reportedly not happy about his JustFriends status.
15* StarMakingRole: ''Tommy Boy'' was Creator/ChrisFarley'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 ''Film/BeverlyHillsNinja'', his untimely death in 1997 put a premature end to what could have been a long and successful film career.
16* ThrowItIn: 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.
17* TroubledProduction: The plan was for Farley and Spade to quickly complete the film during their summer break from ''Series/SaturdayNightLive''. 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.
18* UncreditedRole:
19** Creator/RobLowe 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.
20** Fred Wolf worked on the screenplay uncredited.
21* VindicatedByCable: 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.
22* WhatCouldHaveBeen:
23** Tommy's name in the original script was actually "Billy." Creator/LorneMichaels requested it be changed to avoid confusion with ''Film/BillyMadison''.
24** 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!
25** Creator/ChristianSlater was considered for Richard. Creator/ChrisFarley pushed for one of his two [[Series/SaturdayNightLive [=SNL=]]] co-stars to play Richard: Creator/DavidSpade or Creator/AdamSandler. Sandler wound up shooting ''Film/BillyMadison'' instead, so Spade got the role.
26** The character of Helen the Waiter was originally written for Creator/RoseanneBarr, but she was unavailable.
27** Scheduling conflicts almost forced Creator/RobLowe 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. Creator/MatthewMcConaughey was one of the actors who auditioned. Eventually, Lowe's scheduling conflicts were resolved, and he was able to appear.
28** Creator/FarrahFawcett was considered for Beverly.
29** 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.
30* WorkingTitle: The film was initially titled ''Rocky Road'' and kept that title for so long that the marketing team even made [[https://www.businessinsider.com/original-tommy-boy-poster-when-called-rocky-road-2013-12 posters featuring it]]. Then it was called ''Billy the Third: A Midwestern''. However, Creator/LorneMichaels was also working on ''Film/BillyMadison'' 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''.
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