Larry being chased by Tuddrussell (with a pair of jeans), Otto, Winston Churchill wearing a dress, Roosevelt wearing an Eskimo parka, and Stalin in a tourist outfit in "The Prime Minister Has No Clothes" in a Benny Hill-esque chase scene, complete with the tune of Yakkety Sax. It Makes Sense in Context, honest!
One of the best moments is when the Squad goes back to find Edgar Allan Poe, who has turned into Tastes Like Diabetes Incarnate. After he reads them "The Bear" (the kid-friendly version of The Raven), and it is the most cheesy, schmaltzy, Sugar Bowl thing ever written, and after he finishes, the stunned, shocked, and even horrified looks on the Squads faces are absolutely the pinnacle of hilarity for this show. What makes it better is Tuddrussell's delayed jaw drop.
Another from the Poe episode: Poe goes to a hospital to cheer up patients Patch Addams style. He changes into a clown costume behind a curtain, but the curtain is around the bed of a man in traction and a full body cast. The only part of the guy able to react to what just happened are his eyes.
And yet another: the trio take Poe to a forest that was destroyed by a fire. Instead of becoming depressed again like they'd hoped, he starts traipsing about, putting party hats on all the burnt animals. "Here you go, crispy moose! It's party time!"
To top that off, Otto's reaction-
Otto: Aww, look how cute that moose looks in the little party hat!
After spending the entire episode trying (and failing) to turn Poe back into his gloomy historically-accurate self, his Berserk Button turns out to be criticizing his cake.
When the Founding Fathers are trying to write the Declaration of Independence and John Adams tries to "help" by shouting random words. "You're no help, Adams!"
Tuddrussel and Larry's attempts to get by without Otto's help are on Crowning Moment of Funny after another. Tuddressel's first plan is break into the founding father's hiding place and beat the living shit out of them, and then leaves saying "Now you all get right with a, history," and they respond "What was that all about?" after he leaves. Their next plan consists of helping Benjamin Franklin invent the light-bulb, and talking to Otto and finding out exactly what is wrong with Ben Franklin, they break into his house, break the light-bulb and stuff him and sack and bring him to the rest of the founding fathers, whose reaction to seeing Tuddrussel is "Ah, it's the maniac!"
In the episode where they meet Buffalo Bill, they find him as a lunatic conspiracy theorist. He argues with Otto over that Abraham Lincoln had a giant hypnotic eye underneath his hat and that Thomas Jefferson had special relationships with aliens.
Buffalo Bill: It's all right here in the twenty dollar bill, man! You see right here next to
the White House and next to the bushes, an alien saucer!
Otto: What?! That's barbecue sauce!
Buffalo Bill: Yeah, yeah, that's just what they want you to think, man!
Tuddrussel's and Larry's accounts of their mission in "A Thrilla at Attila's" reveal some interesting and hilarious insights into their psyches. Even funnier are Otto's confirmations that some of the exaggerated details in both stories actually happened, such as Tuddrussel immediately punching Attila in the face when they meet and Larry trying to teach the Huns aerobics.
Otto Osworth: Hey, look! We're going to meet the Earl of Sandwich. He invented one of the most popular foods of all time.
Buck Tuddrussel: Well, I hope he invented more than one, 'cause I'm starved.
Also, when the Earl was showing them his list of failed sandwiches:
Earl of Sandwich: (burned sandwich) This one was too hot, (one in a block of ice) This one too cold, (another covered in slime) this one too icky... (the final one is a nauseous looking one) I don't even know what happened here!
Tuddrussel: (starts eating the sandwich) Not bad!
Tuddrussel: (nauseous burp) This thing's making me sick. (Keeps eating the sandwich)
The Earl of Sandwich does manage to successfully invent a sandwich. He decides to name his invention "Stinky Pile of Poo".
In 'The Island of Dr. Freud', the town hall meeting-
citizen 1: Hey! where's the mayor?
Deputy: well, uhh- he's currently chasing a cat up a tree.
citizen 2: Where's the police chief?
Deputy: He's the cat. Now let me hear your complaints one at a time!
man with bandaged arm: The mailman bit ME this morning!
woman with Wisconsin accent: Mah husband POOPED on the lawn!
a concerned father: My teenager is a pig! (BEAT) Oh, and he thinks he's a squirrel!
Tuddrussel kickstarting the Boston Tea Party by introducing the conspirators to coffee, as well as their later cameo and role as Deus ex Machina in "Betsy Ross Flies Her Freak Flag".
Tuddrussel's overall track record as a Time Squad operative before Otto showed up, he never really seemed to understand the underlying concept of what his job entailed, and instead treated it like a cop gig. Highlights include fining Nostradamus for making false prophecies and then arresting him for swearing at an officer of the law (he was actually speaking German), confiscating Ben Franklins kite for operating electric equipment without a license, and trying to apprehend Lady Godiva for indecent exposure.
One episode involves Time Squad arriving at Johannes Gutenbergs printing shop, only to discover that Joan Of Arc has somehow ended up there. When Otto ponders where Gutenberg has ended up, we find out that he has switched places with Arc, and is doing an abysmal job at leading the French army, being more concerned with the font and design of his war maps than the state of the army, which is suffering a serious beatdown.
In Feud for Thought, where Otto and Tuddrussel paints fighting words on the sides of the Mccoy's and the Hatfield's houses and the two patriarchs find the work.
Randall Mccoy: 'Hatfields Rule'... AUGH THOSE DIRTY HATFIELDS!
William Hatfield: 'Mccoy's rock'...WHAT'S THAT EVEN MEAN?!
From "Old Timers' Squad": The Reveal that Samuel Morse has already invented the telegraph, he was just using it to send funny beeps to his girlfriend across town, and had instead tried to campaign for yelling like a lunatic out the window as the new revolutionary form of communication. Time Squad is less than impressed.
An off-screen moment of funny happens in the episode where Otto gets sick and cant help the others to deal with Ben Franklin quitting politics ("Floundering Fathers"). The start of the episode has the team in Czarist Russia, where their mission had apparently been to get Karl Marx to give up a career in building the largest igloo in the world. A similar funny pre-main plot joke is in Cabin Fever, when the team have just finished up a mission to get Louis Armstrong to get back to playing music, instead of his plan to drill to the center of the Earth. Whats even funnier is that they were apparently forced to resort to physical force, and that Armstrong kicked their ass.
From "Horse of Horrors": Otto, Larry, and Tuddrussell getting mauled by the ersatz My Little Pony that Paul Revere received as a birthday present (which is what led to his being scared of horses).
Larry crying over Tuddrussell not remembering his birthday and Tuddrussell tricking him into thinking he cares about him:
'Tuddrussell: Aw, I'm sorry. I want you to have a happy birthday. (puts hand on Larry's shoulder): I love you, buddy.
Tuddrussell(cracks up): No! (walks away as Larry continues sobbing)