The ultimate fate of the “fucking hippies” in *Once Upon a Time in Hollywood *.
I loved the absurd out-of-nowhere drinking game scene in*** Shanghai Noon***. Both Jackie Chan and Owen Wilson seemed to be having the time of their lives.
If you want to talk Woody Allen, how about Howard Cosell’s interview with an assassinated dictator in Bananas?
And a truly inspired piece of silliness in a silly movie. “I speak jive.”
The magazine scene from Bananas.
I always thought the bicycle scene (Raindrops Keep falling On My head) in Butch Cassidy And The Sundance Kid was absurdly at odds with the tone of the rest of the movie.
j
In Mel Brooks’ Hitchcock-spoof, High Anxiety, there’s a scene in the mental hospital where Mel and the corrupt administrator (played by Harvey Korman) are doing patient evaluations and come across a man who suffers from unexplained sudden sharp neck pains and hallucinations with werewolves. While Mel’s character interviews him, Harvey (who’s behind Mel’s back) pulls out a rubber band and shoots the patient in the neck triggering the “unexplained” neck pains and then pops a pair of cheap plastic Halloween fangs in his mouth and begins making “scary” hand gestures. The premise of the scene is dumb but it’s also hysterically funny the way it plays out.
The scene in Sideways when Miles and Jack go back to the house where Jack leaves his wallet. Jack convinces Miles to go into the house and retrieve the wallet. Miles gets the wallet but is chased by the naked husband of the wife that Jack had slept with out to the car.
Top Secret!
Val Kilmer and Lucy Gutteridge are recounting some of the movie’s backstory.
“It all sounds like some bad movie.”
A moment of awkward silence, and they both glance nervously at the camera.
And then there were the scenes with the cow.
The silliest scene in a movie full of silly moments,the attack of the German Nihilists in the bowling center’s parking lot in the Big Lebowski.
…and the Swedish bookstore, where it takes you a couple minutes to figure out what’s going on. 
Without doubt, it was Bela Lugosi’s death scene in “Plan Nine from Outer Space.”
He is seen to wander aimlessly around his front yard, while mourning for his dead wife, with Criswell (I think) providing unintentionally hilarious narration.
Lugosi then wanders off to the right of the screen. A scream is heard, followed by the sound of car brakes. We then cut to his funeral.
I was floored when the otherwise-fairly-serious Bruce Cockburn closed a concert with this. Of course, he got everyone whistling along…
Anyone who likes silliness enough to even open this thread needs to go watch the original Bedazzled (the above nuns-on-trampolines, Peter Cook as a rock star… and as the devil, ripping the last page out of each Agatha Christie paperback in a crate of books).
And do watch Rat Race.
Too many scenes to list… maybe Mr. Bean and Newwwwman “hauling assss”, or Jon Lovitz’s rather-Jewish family stopping at the Barbie Museum… well, it turned out to be the Klaus Barbie Museum, and they end up stealing Hitler’s staff car.
(in case you’re wondering, it’s a remake of Mad, Mad, Mad, Mad World… with John Cleese in charge, presenting the rules of the race)
Nothing compares to Barbara Billingsley speaking jive in Airplane!:
“Cut me some slack, Jack! Chump don’ want no help, chump don’t get da help!”
You shoulda bought a squirrel.
That scene was pretty silly, but the silliest scenes in that movie were the ones with Johnny.
“Johnny, what can you make of this?”
“This? Why, I can make a hat or a brooch or a pterodactyl…”
The “Stateroom Scene” in the Marx Brothers’ A Night At The Opera.
The first movie that popped into my head was My Favorite Year (1982).
Particularly the restaurant scene where Peter O’Toole intends to whisk away the ravishing young redhead from beneath her thuggish escort’s very gaze, and enlists the young tv writer played by Mark Linn-Baker to assist him.
The climactic scene, also.
Oh if we’re doing unintentional comedy, the wig scene in “Valley of the Dolls” is the runaway winner. Two Oscar winning actresses delivering dialogue that drag queens couldn’t recite with a straight face.
How silly can you get!
Joan Crawford in ‘Torch Song’. An interminable time is spent showing her bored as F, lolling around in her bedroom, looking at the clock, smoking, looking out the window. ENOUGH! you want to yell…of course, her ridiculous ‘blackface’ dance number, where she takes off her wig at the end revealing carrot orange hair, that makes up for it.