- One pitch accidentally dissolved into Toilet Humour, which made them all break down in laughter (Season 1 Episode 6, "Toilet Snake").
- In the first episode of Series 7, there was a product so good that all of the Dragons started negotiating. One pair of Dragons then asked if they could "go to the back of the room to discuss for a moment", jokingly echoing the request they had heard frequently for six years.
- The third pitch of the first episode of Series 8 has all of the Dragons (with the exception of James Caan who doesn't invest in alcohol related pitches for religious reasons) getting into a massive argument between themselves over whether the business they're looking at is worthless or not, with the entrepreneur looking on in bewilderment.
- A number of the pitches shown inbetween the four main ones could qualify.
- Season 9 ep 2 had a pitch for an inflatable bed...in a car. It was amusing enough when Theo got in, but it was even more hilarious with the addition of the 6ft 7inch Peter Jones. The Dragons were all in such hysterics that it got to the point that Evan Davis decided to remind the viewers that at the end of the day, the bottom line's all that matters to the Dragons.
- During Junior Dragon's Den, we get this gem:
- The whole of Lord Sugar's appearance for Children in Need, from him complaining about the den itself, mocking the Dragons for having business meetings in an old warehouse, and trying to pass off a Pudsey doll as a "wireless communication bear."
- The UV Body Sculpture pitch, and watching the dragons get increasingly frustrated as they have to almost beat the information out of the entrepreneur, who has nothing but a sheet of paper that he thinks some people might possibly want to buy. Duncan has to get up and do his demonstration for him, Deborah tries in vain to get any sort of business idea out of him, and then...Duncan: When you lie down on a sunbed, you put this on top of you?Glen: Yeah.Duncan: But most sunbeds now are stand-up sunbeds. So what happens then?Glen: They fall off.
- In Shark Tank, the American version, one pitch has a couple selling ice-cream for dogs. Robert Herjavec lures one of the dogs over with the ice-cream, and lets it sit in his chair. Lori Greiner absentmindedly pets it as the couple speak.
Barbara: Oh, Robert, you look so adorable.
- And then, later, Robert actually drops the dog. All the sharks start laughing - except Robert, who runs over and apologises to it.
- So much of Robert Herjavec's adorkability actually fits in to this category. One episode has a party business that holds a mock party for Mark's upcoming birthday; Mark doesn't really care, but Robert cheerfully wears the complimentary shark-fin hats for the entire pitch.
- The presenters of the "Drop Stop", when questioned, explain that they have a patent for "an elongated foam member with a slot". Cue Mark Cuban sniggering.
- At first, Kevin O'Leary is interested in the "Beverage Boy", but when the discussion and presentation go south, he declares that the entrepreneur (whose first name is also Kevin) has no right to call himself Kevin, and that he's renaming him Zonk unless he can get a deal (and he eventually does). He even suggests renaming the item the Zonk-a-tron.
- In one episode, a mother and daughter pair were pitching Wicked Good Cupcakes, homemade cupcakes stored in jars that can be bought at a local bakery or mail-ordered. Almost all of the Sharks (minus Kevin who ended up investing) had business-related reasons for not wanting to invest; Robert isnt much of a dessert person, Lori isnt a fan of the products two-week shelf-life, and Mark isnt familiar with the dessert industry. Desmonds reason? He loves the product too much and is afraid hell pack on the pounds if he invests in it.
- In the same pitch, the entrepreneurs hand out product samples to the Sharks. Mark quickly burns through two samples and even tries to get a bite of Desmonds sample. It doesnt work.
- Robert, not being a dessert person, doesnt eat his sample. Cue Mark asking for it and the Sharks casually passing it down to him since he and Robert are on opposite sides of the panel.
- Robert Herjavec's just as Adorkable in the Canadian Dragons' Den. One episode has him volunteer to try out a trampoline, and partway through a loud rip is heard.Robert: I ripped my pants.
- One episode in the Australian version had a guy pitching his "subscription underwear/socks" business to the Sharks. His presentation started out fairly simply (having little mailboxes with sample packs inside) and then he decided the best way to get the point across was to pull a pair of his underwear...out of his crotch, with the line "Hey look, I've just made a delivery!" The female Sharks found this hilarious, to the point where they both made him an offer!
- Australian version: The "tapping alarm clock" pitch had Glen Richards climbing into the bed to see how it worked. Once it went off, it would tap the user on the chest (gently) until you hit the snooze button. Glen goes to hit the snooze button...and it doesn't stop tapping him.
- One episode on the Australian version had radio hosts Fitzy & Wippa pitching a joke product to the Sharks known as the "mup" (mint in the bottom of a takeaway coffee cup to help with coffee breath). Pretty much the entire pitch from start to finish was hilarious, culminating in the person dressed up in the "mup" costume having Wippa pull out a foam mint from between the person's legs.
- The inventor of the automated lollipop control system (for roads where trucks are coming in and out all the time at a construction site, but closing the road is not required) came on the show seeking "Someone to help [him] launch the product and a carton of beer." The facial expressions of all five Sharks were utterly priceless.
- Season 1 of the Australian version had two guys pitching their talking bottle openers. They'd received a couple of offers and went out into the hall to discuss them. Meanwhile back in the boardroom, Andrew suggested going into a 50-50 joint offer with Steve(?). Cut back to the hall and the guys were discussing the possibility of a joint offer...for the exact same amount Andrew had been proposing in the boardroom! When they came back in and asked about the possibility of a joint offer, Andrew's first reaction was "Can you read minds?!" followed by him asking if they'd hidden a microphone in one of the bottle openers.
- In the U.S version, Dr. Doofenshmirtz from Phineas and Ferb is featured on one episode as an extra at the end. Hilarity Ensues as he tries to find a way to get the Sharks to endorse selling one of his -inators.
- Debbie Weaver from The Neighbors goes on Shark Tank to pitch a handbag invention. Unfortunately, she brings Larry with her and, between her lousy invention and Larry's disruptiveness, the pitch is a disaster. So much so that Kevin O'Leary declares himself out before saying "I'm coming back in so I can say 'I'm out' again!".
- Season 3 of the Australian version had Steve trying to make a point to an entrepreneur about why his initial offer was ridiculous, which involved Steve and the entrepreneur swapping seats (literally). Steve repeats the guy's original pitch only for the guy's response to be "That's a fantastic product, I'd love to make you an offer!"
- Season 3 of the Australian version had one group of guys pitching their utility guitar strap product. During the handout of samples, Steve folds one in half, smacks it against his hand and makes a comment about how it could have other uses. The guy's comment was "that's next!"
- Season 3 Australia: one of the failed pitches was for a product called "Pocket Balls" (essentially themed handwarmers with designs to make them resemble balls...)
- Season 14 of the UK version has this gem: a couple are pitching their line of portable baby beds and similar products, when Touker Suleyman decides to try out one of the rocking beds, only to accidentally break it.
- This scene is made even funnier by the fact that Touker was pretending to suck his thumb.
- On the Canadian Dragons' Den, a truck driver came in to pitch Lyoness, a cashback card service that has all of the hallmarks of a pyramid scheme. The dragons were not impressed, and it's even more hilarious watching them try to explain to him that it's a pyramid scheme.
- People Just Do Nothing had a promotional crossover with the five UK Dragons, in which they pitch a pirate radio station. Hilarity ensued.
- One woman on the Australian version came in pitching her cloth nappies, which featured an insert (which would be changed and washed instead of needing to replace the entire nappy). She then showed off her series of cloth sanitary napkins. Andrew immediately assumes that they're for the nappy, only to be told by all the women in the room at the time what they actually were for, with Steve (of all people) quipping "There's this thing called the menstrual cycle."
- Series 4 of the Canadian version: Arlene asking Bruce McBirney if his Cure-All Water cured insanity.
Funny / Dragon's Den