- Acceptable Targets: John has a good simile when Sack drops his mask at the wedding:John: Wow. Gettin' a nice preview of what marriage is gonna be like with Ike Turner here.
- Harsher in Hindsight:
- It's a bit hard to watch John's Heroic BSoD when Owen Wilson was struggling with depression and contemplating suicide back in 2008.
- John is seen reading a self-help book written for the suicidal (called "Don't Jump! Life is Worth Living!") Where exactly was this book when Owen Wilson really did attempt suicide in 2008?
- Also the scene with Jeremy getting shot by Sack while quail hunting became a bit darker after Dick Cheney's "hunting accident" (he accidentally shot Harry Whittington in the head while quail hunting) in 2006.
- Hilarious in Hindsight:
- The butler calls the family dog a word that sounds like (or is) "snooki."
- Compare Will Ferrell's entrance here to The LEGO Movie.
- Jossed: A long standing rumor was Richard Riehle appearing as an extra in the funeral scene. He denied these in 2017.
- Memetic Mutation:
- "Hey, Mom, can we get some meatloaf?!"
- Moral Event Horizon: If Sack's mere personality didn't make it clear enough how despicable he is, the fact that he's willing to "accidentally" shoot someone (it's unlikely he'd care if he killed Jeremy or John instead of simply wounding them), definitely crosses the line.
- Narm: Sack is such an over the top Jerkass every single second he's on screen that it's impossible to believe he's considered such a catch.
- Nightmare Fuel: Though it's Played for Laughs, the Black Comedy Rape / Double Standard Rape: Female on Male of Jeremy, being unvoluntarily tied up and gagged while sleeping. And Gloria acting very Yandere. And it doesn't end there. Gloria's closeted brother comes in and pretends to do the same thing.
- Retroactive Recognition:
- Unintentional Period Piece: John McCain's cameo As Himself at Christina Cleary's wedding became this after his passing in August 2018.
- Unintentionally Unsympathetic: Much of Gloria's behavior towards Jeremy can come off as extremely manipulative, if not outright abusive; for some viewers, this can make it difficult to view it as a Happy Ending when they get married at the end. Among other things: she angrily pours rubbing alcohol on a bleeding wound when Jeremy tries to turn her down for sex, she ties him to a bed and forcibly has sex with him against his will, and she falsely claims to be a virgin after they sleep together for the first time (possibly to guilt-trip Jeremy into staying with her longer).
- After John seemingly loses his chance with Claire, he goes into a spiral. He crashes many weddings and is shown to be cynical and depressed. We're meant to sympathise with him, but during these scenes he ruins several weddings, including one where he kisses the bride on the lips and refuses to stop.
YMMV / Wedding Crashers