Goofy Print Underwear / Film

Boxers with red/pink hearts
  • The pimp at the beginning of the 1977 exploitation flick Fight For Your Life is shown to be wearing loveheart boxers after Kane and his buddies steal his car and his clothes.
  • Murtaugh from Lethal Weapon 4; when directed by Riggs to strip to his boxer shorts to distract a madman wielding a flamethrower, Riggs asks with a laugh "Are those little hearts?"

Other-print boxers
  • Agent Simmons (played by John Turturro) in the Transformers live-action movie found himself handcuffed to a lightpole wearing some gaudy tropical boxers. Mikaela scoffs at that; the agent is too busy plotting revenge to be embarrassed.
  • In the George Lucas film version of Howard the Duck, the title character was strip searched by police, exposing a pair of red boxers with white polka dots.
  • Christopher Lambert's character in The Hunted wears boxers dotted with cute little pigs, which his lover finds rather amusing.
    Paul: Yeah... I like piggies.
  • The Oogieloves in the Big Balloon Adventure: Toofie's underwear is blue with bunnies on them. Understandable, since the main characters are children...
  • Terminator 2: Judgment Day: When the T-800 enters the biker bar, everyone stares. In-universe, it's because it was Naked on Arrival. During filming, Arnold Schwarzenegger was wearing these to get the desired reactions from the extras.
  • The Amazing Spider-Man 2: Aleksei Systevich wears boxers with rhino faces (appropriately enough).
  • Just standard striped boxers but played for laughs in Help! when Ringo is strapped into a Mad Scientist molecule-enlarging machine to remove a stubborn ring. All his other rings but that one drop off, then his zipper undoes itself and his trousers drop.
  • Rio: As Marcel is parachuting down with his henchmen hanging onto his legs, his pants come down showing his underwear is blue with ducks on them.
  • Scooby Doo Frankencreepy: Shaggy's underwear has junk food prints.

Other men's underwear

Childish women's underwear

Other women's underwear
  • In Anger Management (the movie, not the TV series), there is a scene in which Heather Graham has a cameo as a beautiful but psychotic woman. She invites Adam Sandler into her home (Sandler's therapist, played by Jack Nicholson, has set this all up, but that's not known at the time) and attempts to seduce him by appearing in nothing but Boston Red Sox fan lingerie (with the bra cups resembling baseballs, as I recall) and then starting to peel off the bra. Sandler nervously tells her to stop (he has a girlfriend), but this causes the woman to assume he thinks she's fat and to very slowly have a nervous breakdown, culminating in her screaming at him, throwing a chocolate cake in his face, and throwing him out into the rain.