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Tommy Callahan (Farley) is the Man Child son of auto part factory owner Tom Callahan (Brian Dennehy). Big Tom marries Beverly Barish-Burns (Bo Derek), a new wife with a rather conniving "son" Paul (Rob Lowe), then has a heart attack and dies at the wedding reception. Shortly after, his now-widow and stepson use their stocks to try and sell the company to auto magnate Ray Zalinsky (Dan Aykroyd), putting all the workers at Callahan out of business (which was, of course, their goal all along).
The only way for Tommy to avert this is to sell enough brake pads to make the company profitable. But will a bumbling idiot who took seven years to finish college have enough business savvy to sell enough brake pads...and will he be able to overcome the scheming of his new "family"?
- A Date with Rosie Palms: Richard has one while ogling Ms. Fanservice from his hotel window. Tommy never lets him live it down.
- Actor Allusion: When Tommy's future step-mother first appears she is referred to as being a "ten". Bo Derek has been referred to as being a "ten" before in the movie "10".
- During the flight to Chicago, David Spade is a rude flight attendant. Why does that sound familiar?
- The Alleged Car: Richard's car turns into this during the course of the film, between the M&M's, the door coming off at the gas station, the deer tearing up the entire backseat (and most of the rest of the car), and the hood coming off because of the oil can left in. By the end of the film, Richard parks it illegally and tells the objecting security guard to "keep it".
- Amazing Freaking Grace: Played during Big Tom's funeral.
- Amusing Injuries / Running Gag: Paul
- Breathe on the Fan: Luke... I am your father.
- Catch Phrase: "Son of a..."
- "I've got a plan!" "...Yikes."
- Caught with Your Pants Down / A Date with Rosie Palms: Richard
- Chew Toy: Richard's car.
- Cleveland Rocks: Well, Sandusky, but close enough.
- Danger Takes a Backseat: The deer, in a Crowning Moment of Funny.
- Deadpan Snarker: Richard
- Does This Make Me Look Fat?: "No no no, your face does."
- Door Dumb: Tommy tries to open the front door to the university building, only to find it locked. After panicking and giving up, he slumps down on the steps just as another student calmly opens the adjacent door and walks in.
- Fake Video Camera View: When Richard is filming parts of the wedding.
- Fan Service: The skinny dipping woman at the hotel pool.
- Fat and Skinny: "Fat guy in a little coat! Fat guy in a little coat!"
- Gilligan Cut: Richard tells Tommy they can't take no for an answer. Cut to the first customer saying "no" and Tommy going, "Okay, then" and getting up to leave.
- The Carpenters' "Superstar" is on the car radio - Tommy and Richard both shrug noncomittally about changing stations. Quick scene cut, and they're both singing along at the top of their lungs, tears streaming down their cheeks.
- Gold Digger: Beverly, who marries Big Tom just so she can divorce him later on and take half his fortune.
- Jerkass: Richard, although he evolves into somewhat of a Jerk with a Heart of Gold.
- Karma Houdini: While Paul is arrested and effectively vasectomized, Beverly not only gets away scott-free but gets a brand-new, even richer sugar daddy.
- Justified, since Paul abandoned her while trying to escape and was the one who actually performed sabotage on the company. The only "evil" things Beverly did was marry a man for his money and lie about already being married (and try to sell off the company, but hey that's just business).
- Large Ham: Tommy, of course.
- Man Child: Tommy, again.
- Mood Whiplash: Heartwarming reunion! Gleeful wedding! Tear-jerking funeral. Funny buddy road movie?
- Never Live It Down: In-universe: Tommy catches Richard ogling an attractive skinny-dipper. After some initial teasing, they go to bed:
Tommy: Big day tomorrow. Hope we can keep this momentum goin'.
Richard: Yup. That'd be good.
Tommy: Richard... Who's you're favorite little rascal? Alfalfa? Or is it Spanky? ...Sinner.
- Phrase Catcher / Running Gag: "Did you eat a lot of paint chips when you were a kid?"
- "The Reason You Suck" Speech: Richard gets a very well-deserved one from a prospective client, who calls him out on being a smug, condescending Jerkass to everyone he meets.
- Tommy gets more than his share of these speeches from Richard throughout the movie, too.
- Something Something Leonard Bernstein: Done with the trope naming song (they only catch the chorus and "6 O'clock, TV hour" before it goes down to mumbling).
- Shout-Out: Star Wars.
- Throw It In: While there are probably other examples, "Does this make me look fat?" "No, your face does" is confirmed to have begun as an ad-lib.
- Travelling Salesman Montage: Of course.
- We Care: Zalinsky's ads: "I make car parts for the American working man, because that's what I am, and that's who I care about." The reality: "Truth is, I make car parts for the American working man because I'm a hell of a salesman and he doesn't know any better."
- Won't Take Yes for An Answer: Tommy certainly wasn't expecting someone would buy from him...
- Wicked Stepmother: Beverly was this to Tommy until it was revealed she was already married to Paul, thus making her marriage to Big Tom illegal.
- You Don't Want to Catch This: "Bees! Bees! Oh God, they're everywhere!"