- His overall lovable asshole shtick was hilarious to watch at any given moment. The man was mean, inappropriate, petty, vindictive, selfish, and completely shameless. You either watch him hoping for him to get his comeuppance, or because, secretly, you wish you could say/do one tenth of the things he said/did.
- His commentary of the 1992 Royal Rumble, particularly the moment when "Rowdy" Roddy Piper helps Ric Flair, but turns on Flair once again.
- Pretty much everything he said during said match. It was probably his greatest performance as a commentator (or even a personality in wrestling since his pro-Flair commentary played strongly into the story of Flair's win), so it doubles as a Crowning Moment Of Awesome.
- During WrestleMania VIII after Randy Savage had defeated WWE World Heavyweight Champion Ric Flair for the title, Heenan comes back to the announce booth during the following match and has a Villainous Breakdown that is worth watching the Tatanka vs Rick Martel (the match that followed it) dozens of times to watch him meltdown after losing his meal ticket
- Made even funnier when he paused his tirade to ask Gorilla where the "Lumpy Indians" who accompanied Tatanka went? (He meant Lumbee)
- During a Scott Steiner promo, Steiner says he has the crowd "mesmermized" by his perfect body. Without missing a beat, Heenan says "Tony, he's got them all mesmermized!"
- (While witnessing a kendo stick brawl between Hak and Fit Finlay) "This looks like a fight at a bingo hall."
- On the Nitro Girls: "These girls know how to claw, bite, scratch, rip, tear, destroy, scream, yell, cry -- and that's just putting their makeup on."
- A lesser known, but no less funny, incident was when Tony Schiavone put over "Hacksaw" Jim Duggan as being "a very intelligent man." Bobby's response? To laugh. And laugh. And laugh. For the rest of the match. It was so infectious that even Tony started to laugh eventually.
- This Primetime Wrestling segment, where Bobby Heenan and Vince McMahon are given an embalming lesson courtesy of Paul Bearer. Paul's funny enough on his own, but it's Bobby's reactions to the situation that really make the video.
- During a match between Scott Steiner and Scott Norton, two huge men, Heenan referenced chants of "STEROIDS!" by quietly quipping "I've never seen the crowd so pumped up!"
- After Shawn Michaels famously threw Marty Jannetty through the Barbershop window, Heenans response was "Jannetty tried to dive through the window to escape! What an act of cowardice!"
- After making derogatory comments about The Undertaker and Paul Bearer on Primetime Wrestling, Bobby is forced to eat crow the following week when the duo actually show up on set.
- At Summerslam '91, Bobby Heenan, with the WCW title in hand, went up to Hogan's dressing room to try and get a match out of him (on behalf of Ric Flair)...
Bobby: On behalf of the real World's Champion, Ric Flair, I would like to challenge you, Hulk Hogan, to a match, at any time, any place—
(the door slams, causing Heenan to drop the belt)
Bobby: WHO DO YOU THINK YOU'RE EMBARRASSING?! (pounds on door) YOU HEAR ME?! YOU WOULDN'T BE SAYING THAT IF RIC FLAIR WERE STANDING HERE! YOU HEAR—(picks up belt) YOU HEAR ME?! (shoves camera aside) Turn that camera off; turn that goddamn thing off.
- Gorilla Monsoon and Roddy Piper had lots of fun at his expense over this, with Piper chiming in, "That's why he never married!"
- Bobby Heenan vs Telephone. Telephone wins.
- It happened on Prime Time so often for laughs that the telephone could almost be considered a co-star.
- Heenan's line during The Undertaker's and Paul Bearer's entrance.
- Pick any one of his skits that he did on Prime Time Wrestling with Gorilla Monsoon. Any of them.
- Heck, pick anytime the two interacted on TV or the announce booth, if they didn't say or do anything during the show that made you laugh or smile at least once, something must've been wrong.
[at Sherri Martel
] She's MY pin up girl! Monsoon:
I think you need to see your oculist. Brain:
Nothin' wrong with my feet.
- WCW Thunder, sometime in 1998. The crowd is chanting "Hogan sucks! Hogan sucks!," and Brain asked, "What are they saying, Hogan plays for the Sox?"
- Pretty much any time he's on screen in the DVD The Self Destruction of the Ultimate Warrior. The man is not a fan.
- In re Hulk Hogan's "A Real American" theme:
BRAIN: "That's my second favorite song."
GORILLA: "I'm almost afraid to ask. What's your favorite?"
- (At WCW Uncensored 1995, as Dustin Rhodes and the Blacktop Bully Barry Darsow's truck passes a farmland):
Brain: "There's the downtown area of Tupelo. Did you see the skyscrapers? Two stories."
- Heenan dropping the F-Bomb on Brian Pillman here. That is all.
- During the Wrestlemania IX match between Bret Hart and Yokozuna, the fans start chanting "USA!".
Heenan: Listen to how smart these people are, one guy's from Canada and the other one's from Japan.
- A minor one from Wrestlemania IX: After the Michaels/Tatonka match, Luna attacked Sherri. A little later, JR reports that Luna is again attacking Sherri. JR's rightly outraged. Brain, on the other hand... (It's all in Bobby's delivery)
JR: She's attacking Sherri at the first aid station!
- At Wrestlemania IX, he was introduced riding a camel backwards.
- An epic moment during Heenan's hall of fame speech; at one point he calls the WWE the WWF, which of course is verboten due to the lawsuit with the World Wildlife Fund. Someone in the crowd reacts, and Heenan goes off: "Wait, let me get into this now. You wanna talk about Wildlife?! When I came here they had: 3 Freebirds, they had the Junkyard Dog, 2 bulldogs with Matilda, another dog. You had 2 killer bees, you had a guy with a snake, you had a Hawaiian guy with a lizard ... I'm not done yet! And to top it all off, I'm the Weasel doing commentary with a Gorilla! Dammit!" The crowd goes crazy with laughter and applause, most notably from Shane and Linda McMahon.
-> Another funny moment was when he said that the AWA stood for All the Worlds Assholes.
- There was his infamous but not really serious (we think) about the wrestling fans themselves: "The only things that frighten me about these people is that they can vote and they can breed."