- Critical Dissonance: This movie made Roger Ebert's "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.
- Crosses the Line Twice: Richard taking the passengers on a plane through the standard flight attendant stuff includes mentioning that there's a better chance of them hitting a mountain than a lake.
- Fridge Logic: 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.
- "Funny Aneurysm" Moment:
- 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.
- 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 "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.
- Harsher in Hindsight:
- 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, Chris Farley died suddenly from a drug overdose, and David Spade 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.
- Hilarious in Hindsight: Richard idealized Big Tom to the point of seeing him as a Parental Substitute. A few years later, David Spade was on Just Shoot Me! and Brian Dennehy played his father in a few episodes.
- Memetic Mutation:
- "Fat guy in a little coat!"
- "Holy schnikes!". The special edition DVD was even called the "Holy Schnike edition".
- Playing Against Type: 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.
- "Look, if you want me to take a dump in a box and mark it guaranteed, I will. I've got spare time."
- And "She was kissing him." "So?" "With his tongue." "Ew! He's doing his mommy?" "She's not his mom; they're married!"
- Moment of Awesome: Michelle's shouted threat at the cruel children at the lake.Michelle: Listen up, you little spazoids! 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!!
- Tear Jerker:
- Tom's death, and Tommy's reaction. Say what you want about Chris Farley, but the expression of loneliness he conveyed afterward was quite heartbreaking. It's much more tragic after Chris's own death a couple years later.
- An in-universe example: The Carpenters' song "Superstar" causes Tommy and Richard to sing along with it while sobbing (after each one of them initially pretends to think the song is lame).
- Vindicated by History: 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.
- 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.
- What an Idiot!: 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 losing his virginity to R.T.'s daughter.
- The Woobie: Tommy following Big Tom's death.
- Jerkass Woobie: Richard.
YMMV / Tommy Boy