In the first edition of the Celebrity version, Omarosa was on the losing team and made some comments about Piers Morgan, even questioning his sexuality. Piers and the rest of the winning team was watching on closed-circuit television and returned to the boardroom. Instead of defending himself, he went over to Trace Adkins, told him "Come here, you big, sexy cowboy", and kissed him on the cheek.
On Celebrity Apprentice Trump asks Marlee Matlin who she would fire. Matlin(speaking through her sign language interpreter) said Dionne Warwick. She explains that Dionne is intimidating, and says "People tell me she's a legend and I respect that but-" Trump interrupts her asking "What do you mean people tell you? You don't know she's a legend?" Matlin replies(again through her sign language interpreter) : "Well I'm deaf."
Added to when in another episode, Star Jones leans in to whisper something to Marlee. Again, through her interpreter, she deadpans, "I'm deaf."
In one video extra, Marlee teaches Trump how to say "you're fired!" in American Sign Language.
Season 2 of the original US edition had the winning team enjoy some tennis with John Mc Enroe and Anna Kournikova at Arthur Ashe Stadium. Raj gets into a bet with Anna: She'll serve to him five times. If he returns at least one, he gets a date with her. If he can't return any, he's got to do a dare. He loses, and must run around Arthur Ashe Stadium in his boxers. Andy then gets the evil idea of lobbing tennis balls at Raj—which John, Anna and the rest of the team do.
Season 3 of the original US version ("Book Smarts vs. "Street Smarts") had Bren, who had two which had some Awesome as well:
The first had him on a photography set (the prize for his team was portraits of themselves taken by renowned photographer Patrick Demarchelier, who had done covers of many well-known magazines and was Harper's Bazaar magazine's premier photographer). A model noticed Bren had a bowtie, and he commented that it took a certain level of confidence to wear a bowtie. This got him flocked by several models, which stunned one of his teammates (he'd thought Bren looked like one of Orville Redenbacher's family) and Bren got a picture of himself with four of the models on the couch.
The second had his team win a prize of a day golfing with Trump and Christie Kerr. After Trump offers a thousand dollars if a certain shot could be made, Bren came very, very close (in fact, the closest) to doing it—and nearly getting the astonished Trump to pay up.
Also from season 3, the episode which has the candidates creating graffiti. Trump goes through Harlem to see what the teams are doing, whilst a rap about him plays in the background.
Jennifer M.'s "Zenthura" presentation in Season 4, in no small part due to the despairing reactions of her team-mates, Bill and Carolyn visibly cracking up throughout the whole thing, and the awesomely funny music playing over the sequence.
One episode of Season 4 had Carolyn announcing to the candidates that, with Trump and George away on business trips, she was in charge for that episode. Following that announcement, she goes "So [Trump's] seat looks pretty good" and heads straight for it, much to the amusement of the candidates.
Season 5 had Sean Yazbeck and Lee Bienstock out in California as part of their prize—to do voice auditions for the animated movie Over the Hedge. (Sean would try out for and be cast as "Barbecue Barry" while Lee became "Lunch Table Larry.")
As a team-building exercise in the first episode of series 6, Trump has the candidates work together to set up a tent. Soon after they start, Frank starts trying to take control of the team with loud shouting, that reaches Trump in the mansion next door. Cue Trump yelling at him to keep his voice down, and Frank's face going "Oh Crap" in response.
Gary Busey's "Mechanical Dog" advert for LG in the All-Star Series.
His comments when watching the Series 3 shopping channel task.
Simon:(on TV) ... and they're very intricate and they're challenging as well.
Lord Sugar: You are boring and the product is useless.
(later on, Simon decides to show the trampoline)
Simon: Shall I have a go?
Lord Sugar: Don't, don't, don't! Er, he is. Oh my god, what a pillock!
In series 4,
Sir Alan: I mean, Michael? In your CV, what's the first thing you wrote on it? What did you say in there? You're a 'good Jewish boy', is that right?
Michael: Okay, yeah.
Lord Sugar: You are or you're not.
Michael: I'm a nice Jewish boy, yeah.
Lord Sugar: Because if you're unsure, you can always pull your trousers down and we can check.
In the last regular task of series 4, his congratulation of the winning team:
Lord Sugar: Wow! Super salesman Alex, there. Well done. And you, Lucinda, have learned so much in the last ten weeks that you managed to sell £65 worth out of £11000.
Lord Sugar: Shut up, will you? I'll give you a shovel in a minute to dig a bigger hole for yourself.
Quite a few involving James McQuillan in Series 5:
Lord Sugar: James, I understand reading your CV..it's amazing one of the things you've said here. When you wake up in the morning, you can 'taste success in your spit', is that right? Is that one of your sayings?
James: Yes, you know what...
Lord Sugar: What did you have, a curry last night then?
In series 6, Lord Sugar asked Liz Locke to stop saying she would "take that on board". A few minutes later:
Lord Sugar: ...because since then you ain't done that great. Philip: Well I sold three items last week Sir Alan. Nick: Tell us about pantsman!
His summary of Stuart Baggs' time as project manager:
Stuart’s leadership style leaves me trembling with irritation. Who does he think he is?
In series 7, the candidates, trying to source a top hat at the lowest possible cost, go to a high-end hatter. Nick expresses doubt that this will lead to a low price:
The last time I was in this world-famous shop, who came in? None other than the King of Tonga! And I can tell you, the King of Tonga does not go looking for bargains.
Series 9, Episode 7: The task of the week: Sell caravans and accessories. Nick enters one team's camper van, looks around, sits down... and a teddy bear drops out of the ceiling and bounces off his lap with a plaintive squeak.
From the 'Buy ten items' task in series 4:
Nick: It defies belief. He did Classics at Edinburgh, he's a bright boy, how could he make such a mess of it?
Margaret: I think Edinburgh isn't what it used to be.
From series 5:
Yasmina: Unfortunately the girl that was in charge of the chicken wraps forgot to put chicken to couple of the wraps, but she did a good job otherwise.
Margaret: Someone did manage to add a hair to one of the salads though, as compensation.
From the Series 7 finale:
Margaret: Just one final question: What would you like to tell me about yourself... and try and say it without clichés, and say it very quickly.
Brian Sewell's assessment of Rory's time as a project manager:
There he was, thinking in really...school prefect terms of how you establish authority. "You all take your shirts off and I'll keep my jacket on, that will tell you that I'm in charge." Sod that! It doesn't tell you anything except that you're a bit of a prat!
The reactions of Vanessa Feltz and Trevor Nelson when Syed explains his reasoning for ordering "100 chickens".
Syed: We were told that we were gonna have half a million people, and that's why I ordered 100 chickens. Vanessa:NO, you FOOL! (beat) Trevor: Did one of his brain cells fall out of his head and just leave one in there? Because that is so obvious that you don't need a whole chicken for a pizza.
Melody's spectacularly awful roleplay pitches from the Series 7 biscuit task. The first one was a masterclass in bad bad acting and accidental innuendo as Melody and Tom pretended to be lovers in front of bemused supermarket management, while the second one involved Melody and Zoe pretending to be bestest buds after having had a blazing argument on the shop floor about 5 minutes earlier.
In the English sparkling wine task in Series 8, Tom and Adam were so enthusiastic in their "product research" that by the end of the first day of the task, Adam was reduced to giggling fits while pulling a face that would be Nightmare Fuel if the situation weren't so hilarious, while Tom couldn't even remember what exactly it was they were supposed to be advertising. Despite this, they actually won the task, thanks to...
Jenna's hilariously awful video for the other team, which depicted a bride being given champagne at her wedding, and then throwing a massive tantrum because she wanted English sparkling wine, followed by team-mate Stephen (who also came up with the very French name "Grandeur" for their English sparkling wine) giving an incredibly sexist and condescending voiceover. This led Lord Sugar to comment on their video thusly:
Lord Sugar: I might remind you of Sid James, but I didn't ask you to go out and make Carry On Boozing! I was expecting any moment, Kenneth Williams would walk in and say "Ooh, maître d', where's me Grandeur? Someone's nicked me Grandeur!"
Alex Mills from Series 9, whose Unusual Eyebrows alone make hilarity. Other moments:
After meeting a market trader in Dubai:
Alex: "Fresh viagra(!) I don't need any of that, I'm from Wales!"
Team Endeavour's decision to go with an army theme for their "Away Day" task led to Alex's full-costume roleplay as a Drill Sergeant Nasty Colonel.
And he got really huffy when Leah got his pretend rank wrong!
Leah: "Alex was playing a Sergeant-Major role-"
During a task where teams had to make online dating websites, Alex starred in his advert as Herbert, a creepy bad date.
Alex even had some crowning moments during the prize segments, dressing up seemingly like Del Boy in a Belgium beer-tasting trip and getting his eyebrows groomed at a luxury spa.
The jokes about Alex looking like a vampire were already funny, but the revelation that he sells tombstones for a (un)living took it to a whole new level.
The Dubai episode as a whole. As well as Alex's viagra comment, the best bit was Kurt muddling up centimetres and inches when ordering a flag. The other team got stuck waiting in the same flag shop for what seemed like 4 hours when Kurt and co smugly waltzed past them... only to be presented with a flag the size of a tea-towel. Other moments included Jason describing a falcon hood in a terrible You No Take Candle way to a random passer-by and Leah screaming "oud" at baffled shopkeepers in a Northern Irish accent that only got more incomprehensible as she got angrier.