History YMMV / TommyBoy

* Sugarwiki/AwesomeMoments: Once Tommy starts feeling at ease with his job, he becomes a ''far'' better salesman, culminating in his convincing Doug Zelinsky into buying half a million brake pads [[SlaveToPR on live TV, using his own slogan against him]]. When Zelinsky learns that he'd been snookered on the sale of the company, [[GracefulLoser he compliments Tommy for his shrewdness]].

** Being as this movie features Creator/DanAykroyd, it can be very painful to watch it knowing that Creator/ChrisFarley died just a few years later at the exact same age (33) and in a very similar manner as Creator/JohnBelushi.

** This movie may have been responsible for for many people [[BeamMeUpScotty misquoting a famous line]] in ''Film/TheEmpireStrikesBack'' as "LukeIAmYourFather".

* AndYouThoughtItWouldFail: Creator/RogertEbert put it on his Most Hated Films list, claiming no one in the film was funny and the script had no memorable lines. The film went on to be a modest hit (and would have done better had Paramount not botched the marketing and distribution) with an overwhelmingly positive audience reception, became one of the best selling video/DVD comedies of all time, and had several lines ("Holy schnikes!", "Fat guy in a little coat", etc.) become popular memes.

* CriticalDissonance: This movie made Creator/RogerEbert's [[RogerEbertMostHatedFilmList "Most Hated Films" list]], but it was a box-office hit that also sold well on home video. Website/RottenTomatoes gives a 42% score among critics, but a 90% score among audiences.

** The sudden death of Big Tom is a lot worse now, as Brian Dennehy passed away from his own cardiac arrest on April 15, 2020.
** Being as this movie features Dan Ackroyd, it can be very painful to watch it knowing that Creator/ChrisFarley died just a few years later at the exact same age (33) and in a very similar manner as Creator/JohnBelushi.

* PlayingAgainstType: 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.

** JerkassWoobie: Richard.

* CriticalDissonance: This movie made Creator/RogerEbert's [[RogerEbertMostHatedFilmList "Most Hated Films" list]], but it was a box-office hit that also sold well on home video. Rotten Tomatoes gives a 42% score among critics, but a 90% score among audiences.

* FridgeLogic: When Tommy is being pulled over by the police, he comments that the police will never believe he wasn't drinking even though a simple breathalyzer test would prove he was sober. However, consumption of alcohol inside a motor vehicle is illegal in Ohio and can result in a 30 day jail sentence.
* HarsherInHindsight: The sudden death of Big Tom seems to be a lot worse as Brian Dennehy had suddenly passed away from his own cardiac arrest on April 15th, 2020.
** Being as this movie features Dan Ackroyd it can be very painful to watch it knowing that Chris Farley died just a few years later at the exact same age (33) and in a very similar manner as John Belushi.

** "Holy schnikes!". The special edition DVD was even called the "Holy Schnike edition".

* PlayingAgainstType: Brian Dennehy usually plays Criminals or other despicable sorts. In this he's a lovable guy who truly cares about his employees and has a great relationship with his son.

** The effect of the moths coming through the motel window was achieved by blowing pieces of paper with a fan and it shows.
** Creator/DavidSpade is clearly wearing a bald cap during the bit where Richard is revealed to have been wearing a toupee all this time.

** "Look, if you want me to take a dump in a box and mark it guaranteed, I will. I've got spare time."

-->'''Michelle''': Listen up, you little spazoids! [[ParanoiaFuel I know where you live and I've seen where you sleep]]! I swear to everything holy that your mothers will '''CRY''' when they see what I've done to you!!

** Tom's death, and Tommy's reaction. Say what you want about Creator/ChrisFarley, [[SugarWiki/HeReallyCanAct but the expression of loneliness he conveyed afterward was quite heartbreaking]]. [[HarsherInHindsight It's much more tragic after Chris's own death a couple years later]].

** NiceGuy Tommy calls himself "retarded" after getting weird looks from everyone when he makes a fool of himself on the factory floor. Back in the '90s, the word wasn't considered as offensives as it is now.
** Richard starting to masterbate over a skinny dipper is arguably much more creepy now than it was then.
* VindicatedByHistory: The film was ''slammed'' by critics upon release, but these days it's remembered fondly as a classic buddy comedy film that showcases the great comedic chemistry between Chris Farley and David Spade.
** [[VindicatedByCable Vindicated by Video:]] 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.
* WhatAnIdiot: R.T., the Callahan Auto receiving specialist who's extremely rude and bullying to Tommy even though Tommy is in line to replace the owner and president of the company, and could fire his ass in a heartbeat for insubordination. Lucky for him that Tommy's the forgiving sort, and got his revenge ahead of time by [[spoiler:losing his virginity to R.T.'s daughter]].
** Also, Michelle, for somehow not noticing that Paul tampered with the orders, despite her walking in on him at her computer, and his suspicious behavior afterward.

* ValuesDissonance: Richard starting to masterbate over a skinny dipper is arguably much more creepy now than it was then.

* SpecialEffectsFailure: Creator/DavidSpade is clearly wearing a bald cap during the bit where Richard is revealed to have been wearing a toupee all this time.

* FunnyAneurysmMoment:
** Tommy's plans of impersonating flight attendants and pretending to be a suicide bomber are a lot less amusing in a post-9/11 world.
* HarsherInHindsight:
** The characters' fears of the Callahan factory potentially shutting down and having Sandusky go down with it have gotten worse thanks to businesses implementing lay-offs due to the shaky global economy and causing economic downturns for cities, notably in Flint, MI, which we see Tommy and Richard pass through.
** Big Tom Callahan dies suddenly from a heart attack, with Tommy and Richard as the last two people to leave the funeral. Less than 3 years later, Creator/ChrisFarley died suddenly from a drug overdose, and Creator/DavidSpade was so heartbroken that he couldn't bear attending his funeral. To make things worse, another actor who had a role in this movie, Sean [=McCann=] (who played Frank) also died of heart failure 24 years after its' release. The sudden death of Big Tom seems to be a lot worse as Brian Dennehy had suddenly passed away from his own cardiac arrest on April 15th, 2020.
* HilariousInHindsight: Richard idealized Big Tom to the point of seeing him as a ParentalSubstitute. A few years later, David Spade was on ''Series/JustShootMe'' and Brian Dennehy played his father in a few episodes.

** When Tommy tells Richard he'd finally graduated from college, he says "You know, a lot of people go to college for seven years.", to which Richard replies "[[DeadpanSnarker I know, they're called doctors.]]". Since that time, college education has gotten so expensive combined with better knowledge of college experiences (things such as life events can also derail people from finishing their degrees on time) that it isn't uncommon for people to take at least 5 years to work towards their degree.

** This movie may have been responsible for for many people [[BeamMeUpScotty misquoting a famous line]] in ''Film/TheEmpireStrikeBack'' as "LukeIAmYourFather".

* SpecialEffectsFailure: Creator/DavidSpade is clearly wearing a bald cap to during the bit where Richard is revealed to have been wearing a toupee all this time.

** Big Tom Callahan dies suddenly from a heart attack, with Tommy and Richard as the last two people to leave the funeral. Less than 3 years later, Creator/ChrisFarley died suddenly from a drug overdose, and Creator/DavidSpade was so heartbroken that he couldn't bear attending his funeral. To make things worse, another actor who had a role in this movie, Sean [=McCann=] (who played Frank) also died of heart failure 24 years after its' release.

** Big Tom Callahan dies suddenly from a heart attack, with Tommy and Richard as the last two people to leave the funeral. Less than 3 years later, Creator/ChrisFarley died suddenly from a drug overdose, and Creator/DavidSpade was so heartbroken that he couldn't bear attending his funeral.

** Big Tom Callahan dies suddenly from a heart attack, with Tommy and Richard as the last two people to leave the funeral. Less than 3 years later, Creator/ChrisFarley died suddenly from a heart attack, and Creator/DavidSpade was so heartbroken that he couldn't bear attending his funeral.

* FunnyAneurysmMoment: Tommy's plans of impersonating flight attendants and pretending to be a suicide bomber are a lot less amusing in a post-9/11 world.

* HarsherInHindsight: The characters' fears of the Callahan factory potentially shutting down and having Sandusky go down with it have gotten worse thanks to businesses implementing lay-offs due to the shaky global economy and causing economic downturns for cities, notably in Flint, MI, which we see Tommy and Richard pass through.

* TearJerker: Tom's death, and Tommy's reaction. Say what you want about Creator/ChrisFarley, [[SugarWiki/HeReallyCanAct but the expression of loneliness he conveyed afterward was quite heartbreaking]]. [[HarsherInHindsight It's much more tragic after Chris's own death a couple years later]].

* WhatAnIdiot: R.T., the Callahan Auto receiving specialist who's extremely rude and bullying to Tommy even though Tommy is in line to replace the owner and president of the company, and could fire his ass in a heartbeat. Lucky for him that Tommy's the forgiving sort, and got his revenge ahead of time by [[spoiler:losing his virginity to R.T.'s daughter]].

** [[VindicatedByCable Vindicated by Video:]] 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 VHS releases of all time.