Funny / Tommy Boy

  • This exchange:
    Tommy: No offense; but if I sent a picture of your mom back to my buddies at college, she'd definitely be "Boner of the Month"!
  • The deer Tommy and Richard hit that suddenly wakes up in the back seat and destroys Richard's car.
    Tommy: I swear I've seen a lot of stuff in my life, but that... was... awesome. [laughing] [Beat] ... but, sorry about your car, man. That sucks.
  • Tommy catching Richard having A Date with Rosie Palms and making a Running Gag out of it.
  • Richard's airline announcements are so deadpan-caustic they're hilarious.
  • "Housekeeping, you want me to jerk you off?"
    • "What kind of a motel is this?!"
  • Six words: Fat guy in a little coat.
  • Tommy's answers a question on a test in the opening credits. "Thomas Jefferson, James Madison and Herbie Hancock were all framers of the constitution."
    • Even better, both Thomas Jefferson and John Hancock had nothing to do with the framing of the Constitution. With professors like these, no wonder Tommy got that D+.
  • Tommy and Richard's big, goofy singalongs in the car.
  • A sales demonstration by Tommy Callahan.
  • Let's face it, just about everything Tommy says or does.
  • The waitress gets in a great Deadpan Snarker line as well:
    Waitress: "Sorry, kitchen's closed until 12:30. All we got is cold stuff and desserts."
    Tommy: "Boy, some chicken wings would really hit the spot; are ya sure it's closed?"
    Waitress: "Let me check. *beat* Yep, it's closed."
  • Tommy and Richard have it out on the side of the road - Richard smacks Tommy out cold with a two-by-four, then looks up at a billboard. "Hey, Prehistoric Forest!"
  • "YOUR FIREARMS ARE USELESS AGAINST THEM!!"
  • Tommy and Richard in the car, singing Superstar, by The Carpenters. What sells it is Tommy and Richard previously acting nonchalant about the song playing, the Gilligan Cut, and then seeing them with tears all over their faces.
  • The elderly board woman's obsession with whores coming into town if Callahan Auto gets shut down.
    • The Board's exasperated sigh when she first brings it up.
    • Richard's deadpan response after one of her tangents.
    Old Lady: All the whores running around, shaking their behinds for the men-folk!
    Richard: I kinda like her idea.
    • The reason why she can't shut up about it:
    Old Man: Jesus Christ... Once during the war I visited a prostitute, and my life has been a living hell ever since!
http://tvtropes.org/pmwiki/pmwiki.php/Funny/TommyBoy