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* 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 to do both the show and the film.
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* 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.
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* RomanceOnTheSet: 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.
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* RomanceOnTheSet: The Lorri Bagley, who played the gorgeous blonde woman who goes skinny-dipping in the motel swimming pool 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.
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* 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.
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* DawsonCasting: Creator/ChrisFarley, Creator/DavidSpade, and Creator/JulieWarner were all in their early-30s playing 20-somethings Tommy, Richard, and Michelle.
* DVDCommentary: By Peter Segal.
* DVDCommentary: By Peter Segal.
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* DawsonCasting: Creator/ChrisFarley, Creator/DavidSpade, and Creator/JulieWarner were all in their early-30s late-twenties/early-thirties playing 20-somethings Tommy, Richard, and Michelle.
Michelle, all of whom are supposed to be in their mid-twenties.
* DVDCommentary:By The original DVD release has one by director Peter Segal.
* DVDCommentary:
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* 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 Farley played for the Marquette Rugby team while he attended college there. Tommy is seen wearing a Marquette Rugby jacket in the film.
* CharacterOutlivesActor: Chris Farley died in 1997, but in the 2004 romantic-comedy ''Film/FiftyFirstDates'', 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.
** Chris Farley played for the Marquette Rugby team while he attended college there. Tommy is seen wearing a Marquette Rugby jacket in the film.
* CharacterOutlivesActor: Chris Farley died in 1997, but in the 2004 romantic-comedy ''Film/FiftyFirstDates'', 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.
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* 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. \n** Chris Farley also played for the Marquette Rugby team while he attended college there. Tommy is seen wearing a Marquette Rugby jacket in the film.
* CharacterOutlivesActor:Chris Farley Creator/ChrisFarley died in 1997, but in the 2004 romantic-comedy ''Film/FiftyFirstDates'', Dan Aykroyd 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 2004.2004.
* DawsonCasting: Creator/ChrisFarley, Creator/DavidSpade, and Creator/JulieWarner were all in their early-30s playing 20-somethings Tommy, Richard, and Michelle.
* CharacterOutlivesActor:
* DawsonCasting: Creator/ChrisFarley, Creator/DavidSpade, and Creator/JulieWarner were all in their early-30s playing 20-somethings Tommy, Richard, and Michelle.
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* StarMakingRole: ''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 ''Film/BeverlyHillsNinja'', his untimely death in 1997 put a premature end to what could have been a long and successful film career.
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* StarMakingRole: ''Tommy Boy'' was Chris Farley's 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.
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* CharacterOutlivesActor: Chris Farley died in 1997 but in the 2004 romantic-comedy Film/FiftyFirstDates, 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.
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* CharacterOutlivesActor: Chris Farley died in 1997 1997, but in the 2004 romantic-comedy Film/FiftyFirstDates, ''Film/FiftyFirstDates'', 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.
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** Creator/RobLowe turned down being billed, as he didn't want to have to pay the Screen Actors Guild fees for being in the film.
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** Creator/RobLowe turned down being billed, billed in the credits, as he didn't want to have to pay the Screen Actors Guild fees for being in the film.
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* StarMakingRole: ''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 ''Film/BeverlyHillsNinja'', his untimely death in 1997 put a premature end to what could have been a long and successful film career.
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** Chris Farley played for the Marquette Rugby team while he attended college there. Tommy is seen wearing a Marquette Rugby jacket in the film.
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* CharacterOutlivesActor: Chris Farley died in 1997 but in the 2004 romantic-comedy Film/FiftyFirstDates, 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.
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* CharacterOutlivesActor: Chris Farley died in 1997 but in the 2004 romantic-comedy Film/50FirstDates, 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, at the very least, implies that Tommy himself was/is still alive as of 2004.
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* CharacterOutlivesActor: Chris Farley died in 1997 but in the 2004 romantic-comedy Film/50FirstDates, 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, at the very least, implies that Tommy himself was/is still alive as of 2004.
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* HarpoDoesSomethingFunny: The sales demonstration scene was largely improvised by Creator/ChrisFarley. He only discovered that there was a cigarette lighter right before filming.
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* This movie made it on Creator/RogerEbert's [[Main/RogerEbertMostHatedFilmList most hated movie list]].
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* This movie made it on Creator/RogerEbert's [[Main/RogerEbertMostHatedFilmList most hated movie list]].list.
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* 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.
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* 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 to do both the show and the film.
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** 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]].
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* WorkingTitle: ''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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* 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''.
