In the first Austin Powers movie, Dr. Evil starts an Evil Laugh alone. He doesn't say anything but instead, he turns to his henchpeople and beckons that they join in. They soon start laughing together in a very awkward manner. The problem is, they're not quite sure when to stop, and no one wants to be the first to stop laughing... great awkwardness ensues.
A non-villain example in The Great Race when The Great Leslie and Hezekiah meet Crown Prince Hoepnick. The prince makes several jokes, each time gesturing for the crowd to laugh, which they dutifully do. At one point Hezekiah keeps laughing after every one else stops, until The Great Leslie elbows him in the ribs. Watch it here, starting at 0:20.
In Labyrinth, Jareth the Goblin King laughs just before the "Dance Magic" sequence. He quickly notices that his goblins are not joining in and asks, "... Well?" The goblins start laughing, only for him to quiet them down for his song.
In UHF, when R.J. Fletcher starts laughing, the two managers under him realize, after a short pause, that they'd better start forcing themselves to laugh along with him.
In The Big Bang Theory, Raj goes to work for Sheldon. Sheldon plays one of his awkward pranks on Raz and after informing him of the fact that he was joking, mentions, "I'm your boss now. You may want to laugh at that."
In the episode "A Christmas Carol", Kazran does this and follows it up with a "That was funny!"
Earlier than that in the episode "Dalek", Van Statten's "in-tru-da window" joke is met with dead silence, to which he clarifies "In-tru-da window, that's funny!" at which point his goons get the message and join in.
In Scrubs, after finding out his interns don't really find his jokes funny, he tells them to only laugh when they are. When they stop laughing at his jokes, he orders them to start laughing with him again when he makes jokes.
Subverted in Angel when Darla teases Lindsey and she and Drusilla start laughing at him. Lilah isn't told to, but starts laughing with them. She promptly gets a "Shut up" from Darla and a "Shh.." from Drusilla.
Its sequel, Umineko: When They Cry, also plays this for drama, though a bit differently. In Alliance, when Kasumi Sumadera has trapped Ange and is tearing through Maria's grimoire, laughing at her spells, she comes upon the image of Sakutaro, cracks up, rips it in half, and demands that all of her henchmen also laugh at it. This time it's used more to underline her pathetic, bullying behavior.
In Codename: Kids Next Door, there is a boss man who wants to capture LIVE Rainbow Monkeys and do some horrible thing with/to them that is never mentioned:
Boss: And then, we'll take those Rainbow Monkeys, and... *whispers to henchman Simon, they both laugh*
Boss:Shut up Simon!
Simon: Yes, sir...
The Trope Namer comes from Freakazoid!. The eponymous hero's eventual Evil Counterpart, Guitierrez, would often laugh while surrounded by his cohorts. He would then gleefully tell them, "Laugh with me." Keep in mind, Guitierrez was voiced by Ricardo Montalban in full-on Khan-mode.
Inspector Gadget has an inversion: Dr. Claw frequently punishes his cat for laughing with him.
In Kick Buttowski, Gordon Gibble snaps his fingers every time he want his henchmen to laugh at something he just said. Ronaldo demands the same thing from his pit crew the episode "Mellowbrook Drift". At one point he says: "Laugh harder!" On another occasion, he stops them, stating "It wasn't that funny!"
In one episode of My Life as a Teenage Robot Smitus monologues about his evil plan and then lets out an evil laugh, while his minions just stare. He gives them an icy glare and says, "You laugh too." The minions all start laughing themselves silly, so much so that they accidentally let the episode's Applied Phlebotinum out of their ship's airlock.
Non-villainous example in The Simpsons episode "Homer vs. Patty and Selma", Homer is forced to borrow money from Patty and Selma. They agree to help him out on the condition that he become their slave until he repays the debt. They then begin smirking and laughing, and Homer chuckles a little with them at first. Eventually he starts to genuinely laugh more so than those two, who then get a little annoyed at him.
In B.O.B.'s Big Break, from Monsters Versus Aliens, Dr. Cockroach laughs evilly after B.O.B. ends up getting the power to read minds and then tells Link and B.O.B., "Come on, laugh with me!" Dr. Cockroach and B.O.B., reading Dr. Cockroach's mind, laugh evilly while Link just rolls his eyes.