The very first season had a moment where the housemates decided to prank Darren by telling him that Big Brother tasked him with cleaning the chicken coop (Darren is a afraid of chickens). Darren's face when he went to the Diary Room and found out Big Brother didn't give him that task is priceless.
From Big Brother 2006, there was a task where the housemates had to all go into the main room and recite the pledge of allegiance to the State of Susie whenever the fanfare played. As you can guess, they would often do this several times in less than ten minutes. Hilarity Ensues when Nikki is trying to take a nap and just about every time she goes to bed and gets comfortable, the fanfare plays.
Nikki was either really good for a laugh or really good for a bunch of annoyance.
Another Nikki moment was where she was told to go to the diary room and as punishment, had to sit in there in silence until Big Brother is satisfied. Nikki then proceeds to throw a tantrum, and after awhile had been in the diary room for about 20 minutes, and only silent for SIX minutes. Some of Big Brother's comments were also funny.
"Nikki, is that silence?"
Pete falling into the pool is just a great bit of slapstick.
And inspeaking of Pete, he had a little too much fun with Automated Big Brother.
Later in the week, Automated Big Brother broke down.
Flood Night in 2010.
From Big Brother 2008, the Electric Shock task. The houseguests had to wear suits that had electrodes in them while three walked to the back and guided a wand through a complex maze. If the wand touched the wire, the housemates would all receive a shock. To say Hilarity didn't ensue would be lying - it was released on DVD for a reason!
Kathreya and her obsession with cookies in 2008.
The song "Cookie Love" that Kathreya and Darnell sang.
With due respects to her, Jade Goody could say a couple funny things that were unintentionally funny. However; people aren't as keen to make fun of her as much for obvious reasons.
The boys enjoying their "girls night in" in 2013. Especially Daley & Dan's DR session afterwards.
Big Brother US
Big Brother 2:
Shannon scrubbed the toilet with Hardy's toothbrush to get revenge on him, and it became a classic moment. However, Shannon's temper crossed over into Dude, Not Funny! territory when she put chips underneath another houseguest's pillow implying she was fat.
Shannon was also called out on her toothbrush scrubbing because it was a health hazard.
In the endurance challenge, Will shifted around so much Nicole let go of the key and was eliminated from the challenge. Even if she was thinking "Wall Banger", it was funny to see what she did in the Confession Cam.
Nicole: And I (silence) lost it! The most IMPORTANT (silence) competition!! AAAAAALLLLL because of Will's ASS!!!!"
Big Brother 4:
There was a Running Gag in the house where Alison's stuffed animal would wind up looking like it committed suicide. One of the funniest was when she found its head in the oven.
For the final question in the HOH competition:
How many days you dated with your ex in this house? Ali (Justin's ex):1. Jun (Jee's ex): 1,000,000.
Big Brother 6:
One week, the houseguests had to hold down buttons in the pressure cooker for a Head of Household competition. Most of the houseguests would get prizes if they lost, and Beau won a Martini bar - so for several hours he just made cocktail after cocktail after cocktail and got trashed. And then Janelle, his Sitcom Arch-Nemesis dropped and begun to have a couple drinks with Beau. April dropped out of the competition so the two wouldn't fight with each other and this exchange happened:
April: I SWEAR! I DIDN'T DO IT ON PURPOSE!
April (in the Diary room): Really, I totally did it on purpose.
At least once or twice, Ivette would be in the Diary Room and instead of her occupation below her name, it simply said "She's gay".
Big Brother 7:
Will and Boogie just did not care to much about the game so in the Diary Room they had those chill town calls.
Another task that Eric was asked to do was to mimic a houseguest. The public voted for him to mimic Evel Dick, and one time, Evel Dick basically throws cereal all over his face while everyone (including Eric) is clearly enjoying it.
The luxury competition wherein Zach, Dick, and Eric had to team up against Jessica, Daniele, Jameka, and Amber into taking off as many shirts from their body as possible and using the letters on the shirts to spell the words out to win the competition. The boys had taken off the letters to spell "Toga" but instead spelled "Goat" while they tried to figure out what the other words spelled. Then Jessica yells "Toga!" on the other side, which had been doing much better. Cue Oh Crap from Zach, Dick, and Eric as they realize they're going to lose.
Big Brother 9:
When Sharon begun to drive the house crazy while baby-talking the guinea pigs, Joshuah and Adam started mocking her in the diary room. Then finally, someone in the writing crew had this funny idea:
Guinea Pig: Sharon should go up on the block this week!
Guinea Pig #2: Yeah! She's crazy!
Even later in the season, there is a montage of everyone saying they weren't lied to, and then the guinea pigs say they weren't lied to either.
When the writers returned from the writers strike, they begun to insert some Funny Moments through editing, such as when the boys were reading the bible, they showed a "Bible Buddies" screen.
Parker walks to the bathroom and hears Jen and Ryan having sex inside. He then looks towards the camera and smiles.
Jeff wins the Coup d'etat by public vote, and he's called to the Diary Room to collect his prize. But he can't quite pronounce it.
After Jessie was evicted, Chima, Lydia, and Natalie held a small "memorial" service in the kitchen and shared wine, acting as if Jessie had died and saying he would be missed. Kevin meanwhile just sat there looking at them weirdly, and mentioned in the Diary room that he was Surrounded by Idiots.
Casey received a punishment from a challenge that he had to wear a banana suit for a week. After the show? He started selling Banana-themed merchandise on eBay.
Big Brother 12:
There was a "punishment" where the houseguests had to stand up and dance whenever music started playing. Hilarity Ensues when Enzo has to get up and start dancing in the Diary room, and when they play it in the middle of the night. Ragan starts dancing while half-asleep.
When Annie revealed that Brendan has a Masters degree in Physics which he was keeping secret we get confessionals from both Andrew and Ragan both who lied about their jobs of being a Doctor and a College Professor both bragging no one knows their job.
Andrew: Good thing no one knows i'm a Doctor!
Ragan: Good thing no one knows i'm a College Professor!
Britney was good for a lot of laughs! When she was tethered to Brendon thanks to a challenge talking how he had to take a chum dip every couple of hours, you could see her mouthing "Help me" in the diary room.
In the first competition wherein houseguests would ride across on a giant hot dog to the other side, Britney was told she couldn't compete after she fell and hurt her ankle.
"I lost my dignity on a giant weiner."
The Zingbot. It's clear the houseguests were having fun, too.
Dominic and Brendon have a superhero fight in the back yard
This was funny due to the editing. We see Jeff and Jordan talking to each other while Rachel and Porsche are running laps around the back yard. Every time Rachel runs by, music plays, and then stops whenever she runs out of sight. Then Rachel falls down.
That footage of Keith trying to get all the milk out of a fellow contestant's sponge suit for a competition is clearly not going away anytime soon.
The first veto competition, in which both Keith and Porsche (who are partners) are throwing it. This leads to this perfect cut to the diary room.
Porsche: "I'm throwing the Veto competition and Keith has no idea."
The look on Adam's face (and his overall reaction) when Tori Spelling walked into the house. One has never seen a grown man Squee like so before.
Jordan, "We beat all odds!" This is extra funny considering that Jordan had been bailed out by a combination of Pandora's Box and two challenges that were tailored to Rachel's strengths.
Big Brother 14:
Frank's argument that Shane should use the Veto on him one word "Apreesshh".
Danielle and Jo Jo comparing their New York and Southern accents.
When Willie called a house meeting with no coaches, everyone started asking "Where's Boogie?", including the Coaches who weren't allowed on the meeting, thinking he was leading it. Jump Cut to Boogie sleeping.
Another similar moment happened when Janelle was trying to convince Shane and Britney to keep Joe in the house after a small argument, Janelle says she has to talk to Joe to convince him to deal with Shane saying that Boogie could be talking to Joe cut to Boogie, Frank and Ian talking about working out.
Ian appears to be trying to do some funny things, like poking around the house, running around naked...
Boogie saying that he used to work with Dr. Will, one of the greatest players of all time, now he works with Ian who kicks himself the face, saying that someone should kick him in the face.
They got Dr. Will to make a cameo talking about which coach has the best strategy, who would win etc but what was really funny was who Will thought was going to win.
Will: I had to guess it would be Ian. Some people would think Ian and Boogie have nothing in common but that is not true because Boogie is just a forty year old Ian.
Ashley talking about the "Spiritual world", coupled with Britney's weird face since she was obviously having none of it.
Boogie during an argument with Frank and Ian.
Boogie: This is the Big Brother house. We can bounce checks.
Britney talking about Janelle's lack of emotions.
Boogie sitting in the diary room saying that he drafted the brains and the brawn. Pan out to Frank in a spiritard and Ian in a dog suit.
Frank: Go team.
Zingbot returns for his third time to deliver more glorious zings, but the best one by far, even considered so by the houseguests, was the one for Danielle
Zingbot: Hey Danielle, I heard Shane's getting you something after the game...a restraining order! Ziiing!
Britney zings Boogie by saying Boogie's eyes are too busy looking up due to his Botox.
Ashley epically failing at the veto challenge. Then after the veto...
"Awww it's a baby Zingbot. I love babies!"
The "Baby zingbot"
When Joe's family was introduced, suffice to say, he gets a few zings from his own family.
Joe's kids even got in on the act, and say "Turn down the volume!". Heck, Joe's wife even says that amongst the gameplay advice she'd give is to turn down the volume.
Joe's son says to shave that white-thing on his face.
Jen trying to squeeze the lemon juice from Danielle in a Have Have Not challenge. Understand that this is pretty hot on the heels of Danielle getting over some ignorance of lesbians, and in a challenge where one person is to help other teammates wring out a padded suit wring out lemonade that they are soaking u. Cut to Jen, not only riding Danielle, but GRINDING in the process.
Boogie gives a really really rude bye message to Janelle. Britney gets back at Boogie by giving him a similar burn.
Joe's goodbye speech, which he was forced to make after a physically challenging veto competition, consisted of him pantomiming "kick her out and keep me".
Frank's been more than willing to wear silly costumes, such as a carrot suit and the unitard. He even tried to lobby for his safety while wearing said Carrot-suit, and admitted people would take him more seriously.
After Jessie's fifth-time returning, he leaves out the front door and Frank says the one thing we've been wanting to say to Jessie since 2008.
Frank: "..And don't come back!"
The second double eviction has several.
While attempting to have a private conversation with Dan, Jenn accidentally closes the door on Ian's fingers.
Dan then tells Jenn to leave, & Ian believes Dan's addressing him, and attempts to leave, before Dan calls him back.
At the nomination ceremony, Joe puts himself in the nominee seat before Dan has even announced who he nominated.
During the second eviction, the houseguests take their time coming to the living room, so Julie hilariously says "In the living room. Now........ don't make me come in there."
During Joe's eviction interview, Julie asks Joe once & for all what that white thing on his chin is.
Big Brother 15:
After being nominated, Candice told the others she wasn't going to just sit in the corner & cry. Cut to her crying in the Diary Room.
Andy says, "It's not every day you get to see baby pictures of the devil". The Devil referring to Aaryn.
Amanda saying she was afraid that Clowny, Aaryn's stuffed clown, would come to life and kill people.
Julie Chen zings Aaryn, Jessie, and Nick. in one, The biggest gem comes when Nick realized that Gina Marie was the only one who was really into him.
"Well maybe you should have kissed Jessie - she'd give you a vote."
Week four, wherein America was the MVP and they got to vote on the nominee (and subsequent replacement). Hilariously, enough people voted Elissa that she got nominated.
Week five. Aaryn won head of household once more... and Amanda gave a hilarious diary room entry where she talks about Clowny. Then he gradually slides into the shot. Amanda has a lot of fun with it!
Andy talking about how the hammock is his place to relax and think about things... after which he is nearly attacked by a small bird in said hammock.
Everyone cracking up during the Week 6 nomination ceremony. Production even had the dramatic music suddenly die out when Judd started laughing.
Cutting off the basic necessities, Gina Marie spends 30% of time doing nothing and spewing mean things, spends 30% of time obsessing over Nick, and 50% of her time doing over the top stuffs that makes people wonders that if she is really over 30, her HOH blog that she written certainly told everyone that she is a trainwreck.
Helen and Gina Marie have a heart to heart discussion about one another's families. When Helen brings up that her Korean mother has difficulty understanding English, GM comments that it "would be like living in a different country".
Before Amanda's eviction, Elissa trades her(who decides to keep her further)wedding ring with Amanda's wedding band as a promise. Why it is funny? Because this move is originated from BB13, where Shelly trades her wedding ring (that is revealed to be fake) with Rachel, ELISSA'S SISTER, to lengthen her stay in this house.
Judd's punishment of the "Gift of health", repeatedly annoying him in the diary room.
Big Brother 16:
Everyone thinking Donny is ex military - the editors had so much fun with that. Bonus points because they're completely wrong.
Devin broke the door on the way to the veto competition.
Everything Michael has done so far in Season 9. From his gay shark joke to hugging everyone enthusaistically as part of the challenge to win the Executive Bathroom for the day. The fact that he has the IQ. of a genius makes it even funnier.
Surly the fish, just Surly the fish. Even when he first talked he had Michael laughing.
Benjamin, the flamboyantly gay housmate provides some pretty funny material like saying "Scusi!" when he makes a mistake or when he called Michael a Bogan.
Surly's reaction to the reveal that the (fake) second house has its own mascot. An octopus named Rodney.
Layla catched Zoe talking to Surly and then Zoe simply claims she is talking to herself. Layla then takes this to Michael who thinks her claims of Surly talking are fake. Which is especially funny as he was the first person to be approached by Surly.
The radio challenge is absolutely hilarious because of how each pairing (Ava and Estelle, Michael and Josh, Ben and Stacy) work off each other for each of their segments. The radio station is called Double B FM and the tagline is "Radio that puts the 'Unity' in Community"
The unwelcome guests task in one of the final weeks and the people they got to enter the house, which included previous housemates, narrator Mike Goldman who still narrated from inside the house and even a ninja. The ninja even becomes an unintentional Call Back when Michael stealthily brings attention to it by telling the others he was nicknamed the "Ginger Ninja" in school (the "Ginger Ninja" being a main ninja in the Friday Night Games in the earlier seasons).
Big Brother Canada
Andrew the vampire, complete with vampiric music.
When Suzette tries to play the veto where you knock out others plates, she accidentally gets her own plate.
During the double elimination, Talla accidentally slips in the Diary Room.
Any time Talla drinks is bound to cause a few of these.
Topaz getting her Bikini line waxed. Everyone hears her screaming and Gary goes up to investigate. After a little while he puts on headphones and starts dancing in front of Talla and Topaz.
Andrew tries to make the foulest thing he can.
Topaz keeps sleeping through the wake-up alarm.
iPod and Headphones! Please go to the diary room!
The "Double date".
On episode 19, Peter is given a task to trick the other houseguests into thinking that Tom is returning. The entire house with the obvious exception of Peter are completely convinced. Emmett and Jillian even look around for the other items thinking there are more items.
Anick trying to win the houseguests over with a Reiki relaxation session. Ika doesn't have any of it and even calls it a "Voodoo spell".
When escorting the three secret houseguests into the house through the back entrance, the production team had the great idea to blindfold them. Hilarity ensued.
And Scott was flirting with the secret agent escorts the entire time.
The three enter the super-secret soundproof War Room hidden within the Big Brother house, and their first reaction is...it's really warm. And Nate really wants to know if he gets a bobble head of himself like the other houseguests.
Paul, Adel, and Kyle jokingly start their own show where they talk about every way they screwed up in the house. Hilarity ensues.
Gary and Peter's weekly rants on the after show about whatever important topic is concerning the house that week, which usually end in take thats to each other.
Allison's enters the house for the firs time while the other houseguests are waiting outside, and spends the next few minutes awkwardly sitting in every chair in the house.
Allison and Jon receive a secret mission: get completely hammered without any of the other houseguests noticing. It results in a dance party in the diary room, and them getting so drunk they start talkingNewfie to each other.
The "I'm getting Beat up" dance.
one week, Canada was the Head of Household. The head of household room played the Canada, Eh? trope Up to Eleven, putting poutine, ketchup chips, and maple syrup as head of household treats in the room with a Canadian Flag in it.
Talla revisited the house.
The montage of everyone falling. However, it also veers into Dude, Not Funny! territory when you realize that some houseguests really got hurt.
Kenny coming out to the house in the most casual way possible.
Kenny: It's a really nice day today...fuck it, I'm gay! Other houseguests: WHOOOAAA!
The side show, introduced in Season 2. It's quite amazing how well Peter and Gary play off of each other.
Marsha gives Adel a mission... and then Big Brother gave everyone else a mission. That mission? Make sure Adel fails his mission!