- In Series 2, his comments on Jo's CV:
She's got MG Rover, OK? Training directors, if you don't mind, about how to make a profit. No wonder they went bloody skint.
- 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:
Liz: I'll take that...
Liz: [Stammers and falls silent]
- Simon. Trampoline. 
- During the flat-letting task in Series 2, Paul and Michelle go out to inspect one of the flats. The moment they walk into the building, a light cover falls on Paul's head.
- James McQuillan's CV included gems such as "I can bring ignorance to the table" and "I put a leash on people who spunk money up the wall".
- A rare moment of snark from Tom Pellereau:
runs a business, which...unsurprisingly, is all to do with talking."
- An exchange of complete groaners during the App task in Series Seven suddenly veered into this:
Leon: There is App-roximately twelve hours to get this App done.
Jim: Are we fast App-roaching where we need to be?
Leon: (Shaking his head) This is App-solutely fabulous.
Vincent: Did you have an App-le?
- Worst Decisions Ever:
- 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!
- And Tre's remark about the dog walker's belt, on the same program:
Tre: I'm not sure that, in the current climate, it's good to look like a terrorist when you're walking your dog.
- 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!
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:
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.
- In Series 10's historical coach tours episode, Karren's response to James singing "The Wheels On The Bus" and "One Man Went To Mow" to the passengers was to stare longingly at the "In Case Of Emergency, Break Glass" sticker on the window next to her seat and calling it "the coach ride from hell" once they arrived at their destination directly to the camera. She was so annoyed, that Lord Sugar revealed in Why I Fired Them that Karren hadn't yet forgiven him for her supervising the team on that task.