- 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".
Otto : Sir, that's a terrible name!
- 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!
- Also from Dr. Freud episode, after Larry explains his dream to the doctor he unsympathetically recoils at him.
Larry: WHAT DOES IT ALL MEAN, DOCTOR? WHAT DOES IT ALL MEAN?!
Freud: It means you're crazy, don't touch me!
- Freud's interpretations are just hilarious in general, but one of the best is when the deputy tells him that he dreamt that he was a watermelon, Freud says it means that he hates his mother. The deputy happily agrees.
- 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".
- The visual gag in the Betsy Ross episode is hysterical when you notice that all of the hippies have pink, glazed over eyes and Betsy sends George Washington 'homemade brownies'.
- 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?!
- The terror campaign Tuddrussel and Otto wages on both families to piss them off at eachother, such as stealing a scarecrow, leading to crows IMMEDIATLY devouring the Hatfields corn down to the last kernel, to pouring cement in the Mccoy's well.
Mccoy member: Ow! This water is hard!
- To add to the shenanigans, the moment they throw a bomb inside the outhouse of the Hatfields just as William Hatfield was heading over to use it. His stunned, blackened face while still sitting around the now obliterated outhouse says it all.
- From "Old Timers' Squad": The Reveal that Samuel Morse has already invented the telegraph, but 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.
- The older version of Otto clearly enjoys in annoying his younger counterpart.
Otto sees that he'll only grow a few inches taller one day
Otto: Hey, wait a minute! Is this as big as I get?!
Elderly!Otto: You'll never make the All-Star Basketball team, that's for sure. Heh Heh!
- 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.
Larry (sniffles): Really?
Tuddrussell (cracks up): No! (walks away as Larry continues sobbing)
- Tuddrussel's Jerk Ass tendencies are REALLY played up in this episode, for great comedic effect. For example, he eats the gift Otto gave Larry, a macaroni drawing of him.
Tuddrussel: The glitter makes it spicy!
- When the guys find out that they're going to visit the American explorers, Lewis and Clark, Tuddrussel immediately exclaims- "Great Ceasar's ghost! Were going to meet Superman!" Leading Otto to groan- "That's Lois and Clark!"
- He doesnt catch on either. When Otto tells him Lewis and Clark will be famous explorers, Tuddrussel asks "But who will stop Lex Luthor?!"
- A bit of lamp shading happens in "Ivan the Untrainable" after Larry discovers what Tuddrussel's been hiding.
Larry: Ugh! You just can't up and kidnap someone from history and treat them like some kind of pet!
Tuddrussel: Well what about Otto?
Larry (painfully knowing Tuddrussel has a point) Ooooh...well you can't KEEP kidnapping people from history. . .
- Tuddrussel tries to "help" Konfucius by himself while Otto and Larry are sightseeing around China. Unsurprisingly, it consists entirerly of Tuddrussel beating the crap out of the poor guy. When the others arrive back and see that the problem is WORSE now, the issue in question being that Konfucius was writing massive tomes of stories that would never appeal to the general public, on top of Konfucius being bandaged and bruised, they ask Tuddrussel what Konfucius had said when Tuddrussel asked him to cut his stories back to simple Aesops.
: You've been beating him like a microwave
and not told him why?! You're a LUNATIC!!
- "The Clownfather", which revolves around Al Capone forcing the clowns of Chicago to switch jobs with him and his gangsters, so he can make sure no kid has a crappy birthday clown like he did.
Clown: *honks horn sadly*
Capone: Well you better learn to like it, OR THE ONLY BIG SHOES YOU'LL BE WEARING WILL BE FILLED WITH CEMENT!!
- Hoo-Hoo, the birthday clown who performed at Capone's tenth birthday party is so bad at his job it borders on Black Comedy. Flashback to a young Capone being "entertained" by a slovenly asshole in patchy clown-paint and an ill=fitting costume.
Capone: Hoo-Hoo was a deadbeat through and through *Hoo-Hoo proceeds to try and inflate a balloon, runs out of breath halfway through, ties it into a random mess of knots which immediatly deflates and eats young Capones birthday cake—with the lit birthday candle still on it*
- Capone and the gang learn what the clowns are doing in Chicago and what begins is a montage of clowns performing drive by shootings with cream pies, scaring people to death by popping out of slot machines and punching people with spring loaded boxing gloves when playing Blackjack.
- In "Dishonest Abe", Tuddrussel, Larry, and Otto are listing off pranks that they've done (although Otto's isn't really a prank).
Tuddrussel: Okay, get this. Once, I loosened the screws on this robot. He goes to pick up this tray of dishes... and his arms just fall off!
Larry: AH! That was you?
- Turns into a Brick Joke at the end.
(Larry's arms fall off) Larry: TUDDRUSSEL! Tuddrussel (laughing)
: It wasn't me, I swear! (cut to Otto holding a screwdriver and chuckling)
- Tuddrussel's solution to getting rid of Sister Thornly by electrocuting her with his taser gun in Eli Whitney's Flesh-eating Mistake. The fact that he has no idea that she's an awful person who would be of all people that Tuddrussel has come across to deserve it makes it all the more hilarious when he whips it out. And then Otto tries stop him by saying "Let me take care of her!", this leaves Tuddrussel to consider this thoughtfully, and he casually hands the kid the taser thinking that Otto was wanting to taser her. Otto's horrified face is priceless as he pushes the taser away to insist on using 'words' to get her to leave.
- From "Child's Play": Larry thinking the greatest writers in history are Danielle Steele (who writes women's mysteries) and Jackie Collins (who writes sleazy, almost soap-operaish novels about celebrities -- a lot of which are based on real-life ones -- being naughty, whether it's committing murder or having hot, naked affairs with other people).