History Film / TommyBoy

* MistakenForTerrorist: Well, mistaken for bank robber. Twice in fact: The first time, he simply yells "Listen up! This will only take a second!" and everyone drops to the ground. The second time, he's StrappedToABomb made of road flares, trying to get the attention of the news crew that's only there because of the first mistake.

** Ironically they would spend a significant portion of the flight over Lake Erie and later Lake Michigan.

* TheMountainsOfIllinois: While disguised as a flight attendant, Richard comments that the odds of a water landing are low, he's betting if they crash into anything, it'll be a mountain. Unless they have a very unusual flight plan, they shouldn't be passing any mountains going from Sandusky, Ohio, to Chicago, Illinois.

* BookEnds: The film starts and ends with Tommy, in boyhood and adulthood, trying to get somewhere in time (school/a dinner date with Michelle), only to get hit in the head, saying "Son of a- That's gonna leave a mark." afterwards.

* MountainsOfIllinois: While disguised as a flight attendant, Richard comments that the odds of a water landing are low, he's betting if they crash into anything, it'll be a mountain. Unless they have a very unusual flight plan, they shouldn't be passing any mountains going from Sandusky, Ohio, to Chicago, Illinois.

** An especially poignant one for Tommy is during the first board meeting after Big Tom's death, when Tommy is willing to sacrifice everything he has and go on a business trip that he KNOWS he has no experience handling in order to save the company. He may not be intellectual, but his heart is clearly in the right place when the time comes.

* FailedASpotCheck: Michelle fails to notice that Paul changed the quantities of various orders on the computer, despite walking in on him sitting at her computer and typing, and acting suspiciously afterward.

* FailedASpotCheck: Michelle fails to notice that Paul changed the quantities of various orders on the computer.

* AnswerCut: When Richard objects to the idea of him going on the sales trip with Tommy, Frank Rittenhauer asks him if he has a better idea to save the company. Cut to Tommy and Richard hitting the road.

* BerserkButton: Tommy puts up with a lot of abuse from Richard but becomes enraged when Richard accuses him of being a disappointment to his father's legacy and taking advantage of him. Meanwhile, Richard loses his temper when Tommy makes fun of his diminutive stature.

* FakeVideoCameraView: When Richard is filming parts of the wedding.

* HurricaneOfEuphemisms: Tommy uses a few after catching Richard jacking off.

* MountainsOfIllinois: While disguised as a flight attendant, Richard comments that the odds of a water landing are low, he's betting if they crash into anything, it'll be a mountain. Unless they have a very unusual flight plan, they shouldn't be passing any mountains going from Sandusky, Ohio, to Chicago, Illinois.

** Ironically Sandusky is a major tourist destination since it’s home to Cedar Point, one of the largest amusement parks in America, and numerous water parks both indoors and outdoors.

* ShoutOut: ''Franchise/StarWars''.
** "I know."
** Bo Derek wears the same bathing suit she wore in ''Film/Ten1979''. Lampshaded by Tommy when he comments "Dad, she's like... a ''ten!''"
** Is Tommy channeling [[Creator/WilliamShatner Captain]] [[Series/StarTrekTheOriginalSeries Kirk]] the second time he "gets a plan?"
** [[Film/HomeAlone2LostInNewYork "Yikes."]]
** [[WesternAnimation/TheSimpsons Ay, caramba!]]
* SlaveToPR: Zalinsky's public image is all smiles and a WeCare attitude toward everyday workers, but the reality is a sobering experience for Tommy. However, Tommy [[ExploitedTrope exploits]] this by having him sign the brake pad purchase order in front of a live news crew.
* SmartJerkAndNiceMoron: Richard's the right-hand man to Tommy's father, Big Tom Callahan, but comes off as an InsufferableGenius who routinely disparages other people, especially Tommy. Tommy is a bumbling ditz, taking seven years to finish college, but he's willing to do whatever it takes to keep his family's business afloat, even giving up his inheritance. After spending most of the movie struggling to make sales, Richard realizes that Tommy has street smarts when he sees him successfully talk a waitress into giving them a special, and after Tommy learns to [[CentipedesDilemma stop trying to emulate his father and act naturally]], they make many sales.
* SmugSnake: Richard. One client even outright calls him a "smug, unhappy little man who treats people like they were idiots".

* HurricaneOfEuphemisms: Tommy uses a few after catching Richard on ADateWithRosiePalms.

-->'''Tommy''': Richard... Who's your favorite [[Film/TheLittleRascals little rascal]]? Alfalfa? Or is it ''[[ADateWithRosiePalms Spanky]]'' (''chuckles'') ...Sinner.

* ADateWithRosiePalms: Richard has one while ogling MsFanservice from his hotel window. Tommy [[OnceDoneNeverForgotten never lets him live it down.]]

[''The other patrons in the room turn to watch what is goin on, some visibly horrified'']\\

* AndCallHimGeorge: Tommy's LargeHam explanation to the waiter about how he kills sales with his bumbling is a picture-perfect showcase of how this trope works. It also unnerves the waiter enough to make her decide to give him what he wants.

* AntiVillain: Zelensky is a selfish tycoon, but he's more or less following the law and his bottom line.

* BerserkButton: Tommy puts up with a lot of abuse from Richard but he becomes enraged when Richard accuses him of being a disappointment to his father's legacy and of taking advantage of him. Meanwhile, Richard loses his temper when Tommy makes fun of his diminutive stature.

[[caption-width-right:300: Holy shnikies!]]

* YouDidYourBest: Near the end when Tommy mopes [[spoiler:after failing to convince Zelinsky not to buyout the company]], Richard assures him he did everything he could have and Big Tom would've been proud of his efforts.

* DidntSeeThatComing:
** The con artists expected to simply bleed Big Tom dry for about a year before Beverly divorced him and got a big payday. Then he immediately died at the wedding and were put in a situation where they could make more money by selling the company.
** Later on, Tommy and Richard learn that [[spoiler:even though they surpassed the sales goal, several orders were messed up in shipping and many of the customers cancelled their orders. Now the company doesn't have the money need to pay the bank loan and they'll need to sell to Zalinsky.]] Richard remarks that he feels like they've stepped into an episode of ''Series/TheTwilightZone1959''.