- A Big Beautiful Woman does this to a pipeline operator in the James Bond film The Living Daylights as part of a Show Some Leg distraction ploy.
- This was sent up in the Revenge of the Nerds series, with the short character Wormser always ending up with a tall girl (or girls), talking to/dancing between the girl's breasts. And usually Breaking the Fourth Wall by making a knowing Aside Glance to the audience.
- The '70s Chesty Morgan film series, which starred the eponymous Chesty Morgan, an Danish stripper with large breasts (something like a triple J cup) as an assassin who would seduce her targets and then smother them to death in her cleavage. Seriously. Slightly NSFW.
- And the name of the movie? "Deadly Weapons", of course!
- This takes place in Police Academy 3: Back in Training, too: a small Japanese student attempts to seduce Callahan, his hardass Amazonian drill instructor. Callahan immediately pulls him into the bedroom, and then says, "In America, talk is cheap!" She then tackles him down to the ground with his face in her breasts. His (muffled) comment? "I love America!"
- Similarly, in Sixteen Candles the Chinese exchange student Long Duck Dong meets a very tall, athletic girl at a school dance, and slow-dances with her. Because of his height, his face is right in her breasts. At one point, she says she can "run in the five flat", to which he gives her a confused look, then gives her breasts a confused look, and asks "Flat?"
- In the obscure European movie The Real Shlemiel, the Kid Hero's huge aunt is always hugging him this way. And, when a goblin is in the front pocket of his shirt is almost crushed by Aunt Sarah's cleavage. So, the goblin has to jump every time he realizes that Aunt Sarah is about to hug Aaron.
- Happens to Austin Powers in Austin Powers: The Spy Who Shagged Me, when Felicity Shagwell borrows a pair of binoculars still attached to his neck.Austin: Hello, mummy. Mummy, can I have some chocolates? I want some Mars bars! Don't smack my bottom, mummy... Oh, sorry, love. Got caught in your dirty pillows.
- Happens in one scene of Transylvania 6-5000 when Odette the sexy vampire lady (played by Geena Davis) does this to Ed Bagely, Jr in the library.Odette: Face to my breasts! Tell me you want me, too!
- Done kind of Squickily by Pam Ferris to Michael Rispoli in Death to Smoochy. Yeesh!
- Also subverted in a similar way in Dirty Work.Young Mitch: Note to self- Aunt Phyllis is your aunt!
- The Narrator (Edward Norton) of Fight Club gets pressed between Bob's bitch-tits during a testicular cancer support group. The look on his face while being in Bob's bosom is hilarious.
- American Pie:
- When the guys try to set up a bachelor party for Jim in American Wedding, they hire a stripper in a police uniform who has a tendency to punish people via this method. She even punishes Jim's MOTHER via this method!
- American Pie Presents: Beta House a stripper uses this as a method of attack during a bar brawl suffocating one of the guys and shoving him away. Seconds later that stripper head butts one of the other guys into unconsciousness.
- Happens in Honey, I Blew Up the Kid when Diane volunteers to be hit by Wayne's shrink ray while it's in reverse in order to calm Adam down (he's crying after Hendrickson tries to shoot at him, but misses and hits the giant electric guitar, which hurts the giant boy). It just so happens that Nick and his girlfriend Mandy are in the kid's front pocket.
- And their car. Diane is about to breast crush a car. Twin airbags those montains aren't...
- In the MST3K classic Village of the Giants, a guy is picked up by a giantess, who danced with him pressed to her gigantic bosom, clinging to her bra straps for dear life. Quoth Mike Nelson, "First base is larger than I remember!"
- In Fellini's Amarcord, the young protagonist Titta gets pressed against the huge breasts of the buxom tobacconist after betting he could lift her (and is encouraged to suck on them, but end up complaining he can't breath).
- Ulla does this to Max in the 2005 version of The Producers. Not only that, but Max also goes back for more a second time in the same hug.
- In 9 to 5 Dolly Parton imagines doing this in a Dream Sequence as revenge on her sleazy boss who won't stop harassing her.
- Inflicted by Suzie (played by Kylee Nash) on Nate in MILF (2010), who is probably enjoying it.
- Charlie's Angels. Alex Munday poses as a motivational speaker in a tight leather powersuit. After terrifying a roomful of nerdy engineers with her dominatrix act, she then clasps a lucky guy in the front row to her chest while asking if he's come up with any good workplace innovations. With all their fetish buttons tripped, the rest of the engineers are more than eager to show her what they've come up with.
- Done in a not particularly exaggerated manner (although the pair in question does belong to Scarlett Johansson and are obviously very nice) in Avengers: Age of Ultron when Ultron crashes the Avengers' party, causing Bruce Banner to dive for cover over the bar with Black Widow and land on top with his face in her cleavage. He got away with it because they were kinda-sorta beginning a relationship at the time. Actually she seems more worried because he might get overly excited and hulk out.
- In Piranha 3DD, the main character's douchebag uncle who turned the water park into an adult resort is decapitated while trying to escape from the giant flesh-eating piranhas; his head ends up in a stripper's bosom.
Marshmallow Hell / Live-Action Films