Every time Schultz introduces his horse Fritz, who always obediently neighs and bows his head in response.
During Schultz's Establishing Character Moment scene he absentmindedly asks one of the slaves to hold his gun while he fumbles with other things. The slave's face when he's handed a loaded weapon is priceless.
The giant tooth on a spring atop Schultz's wagon. Funny when you first see it, even funnier when they return to town, bouncing away. Look at it go!
The entire "shooting the sheriff" sequence. Remember, bring the sheriff. Not the marshall but the sheriff.
Now call the Marshal.
Everything Schultz does, really, being something of a Heroic Comedic Sociopath. While he cold bloodedly murders people, the offhand and cheerful fashion in which he does so is utterly hilarious.
Django's first choice of clothes as a free man: a royal-blue coat with matching knee-breeches (tied off with blue ribbons), buckled shoes, and a very large, lacy bow tie. It comes off as an 1850s-vintage pimp suit.
Heck, it's more like 1750s. Apart from the deeper blue color and the big cravat, it's almost identical to ''The Blue Boy''. Django is even visible in a reflection in a nearly identical pose...
The film's costume designer admitted that she had slipped Tarantino a copy of The Blue Boy, leading to the final design.
Lampshaded by the slave-girl on Big Daddy's plantation: "You mean you wanna dress like that?!"
Django's expression when Schultz tells him he can pick out his own outfit. It just screams "Oh, I'll be taking full advantage of this."
I can't be the only one who found his Badass pose in the outfit as he calls out "JOHN BRITTLE!" coupled with his Determinator expression hilarious. Made even better a few seconds later when he grabs the whip and starts whipping the white farm hand!
Bait and Switch case: The slave girl at Big Daddy's plantation pointing out the smoke-house "Where Big Daddy hangs all the critters he kills ... poor little squirrels."
Schultz and Django discussing the final Brittle's fate:
Schultz: "Where's Ellis Brittle?" Django: "That's him hightailing it across the field." Schultz: (Pulls out rifle and lines up shot) "Are you sure?" Django: "Yes." Schultz: "Are you positive?" Django: "I don't know." Schultz: "You don't know if you're positive?" Django: "I don't know what 'positive' means." Schultz: "It means you're sure." Django: "Yes, I'm sure. Schultz: "You're sure what? Django: "Yes, I'm sure that's Ellis Brittle." Schultz:(Shoots Ellis through the heart) Django: "I'm positive he dead."
The entirety of the scene with the hooded men discussing how they can't see anything due to the poor quality of their hoods.
Bag Head: I think we can all agree, that while a nice idea, and not pointin' any fingers now, the bags coulda been better implemented.
Django's first meeting with Broomhilda in Candie's place.
Django: Hey there, little troublemaker.
(Hildy stands in stunned silence, then drops her glass of water, and finally faints)
Schultz: You silver-tongued devil, you.
Stephen's expression when Lara says she doesn't want Hildie's whipping scars at the dinner table; he is utterly indignant and almost shocked that she doesn't want to see it.
The first fight in Candieland. Schultz just died, the Dragon's been offed, Django is mowing down plantation workers...and there's one guy who bursts through the doorway, gets shot in the leg, and proceeds to get shot again and again without dying. Even funnier was the lawyer before him.
There is also a bit of fridge brilliance in it. Cora most likely has flat shoes as house worker, while Sheba as mistress has heeled shoes. Likewise Cora has to do work in the house so she should be much fitter than Sheba whose job is to look pretty.
Stephen trying to intimidate Django by saying that he counted six shots, meaning Django used up all his bullets. Django then pulls out a second gun.
Stephen: I count six shots, nigga.
Django:(pulls out second gun) I count two guns, nigga.
Pretty much the entire last couple minutes of the film are a strange mix of funny and awesome, especially when Django calmly walks out of the mansion, puts on his sunglasses, and watches the whole damn thing go up in flames. Capped off by the adorable Broomhilda covering her ears and watching her husband with pride. Django even makes the horse do a "refined" walk while riding it, for both fun and to further piss over the people he just killed.
Django's truely epic trollface◊ at the end of the film after he Blows up the Candyland plantation building also qualifies.