Born Raymond Louis Heenan in 1944, Bobby "The Brain" Heenan is one of Professional Wrestling's most famous managers (and possibly the most successful), working throughout WWE's "Federation Years" of the '80s and '90s as the manager of many a great wrestler and tag team, often running his collective of wrestlers under the name of "The Heenan Family". The Family was constantly opposed by Hulk Hogan, and many of the wrestlers Heenan managed met with bitter defeat at Hogan's hands, despite Heenan's best efforts to ensure their victory. Aside from his managerial duties, Heenan was also a color commentator; he was one-half of (arguably) the greatest commentary duo in the history of the industry (with the late Gorilla Monsoon), and he also worked for WCW for a number of years. Heenan is also an official member of the WWE Hall of Fame.You can read more about his life and career at That Other Wiki.
In fact, that night, when Hogan came out, ostensibly to aid the faces, Heenan (to the derision of the other commentators) was the only one to actually ask whose side Hogan was actually on. The line was unscripted, though, and earned him a reprimand from management for nearly giving the twist away.
According to Heenan's book, WCW boss Eric Bischoff imposed that kind of Genre Blindness on the announcers, since he wanted them to call the action as if it was a "shoot" (real.) Heenan said he told Bischoff that they'd never seen a shoot and that if they saw one they wouldn't know it.
The Cast Show Off: In response to his snarking abilities and willingness to do virtually EVERYTHING to gain attention, Bobby Heenan was awarded his own talk show. Not an in-ring interview segment, not a "Piper's Pit" style roadshow, an actual hour long talk-show!
Several of his 90s-era post match commentaries featured 'The Brain Scan', which simply involved Heenan doodling a famous cartoon character like Woody Woodpecker or Dennis the Menace on the show's Telestrator while putting down a Face wrestler.
Determinator: When word got out that he needed surgery to treat throat cancer, he declared he wasn't going down without a fight, and famously added that if Gorilla Monsoon couldn't shut him up, this wasn't going to, either.
Tony Schiavone asked Heenan why he didn't clap for the Nitro Girls' dance routine on the August 16, 1999 episode of WCW Monday Nitro. His answer: "It's impossible to clap with only one hand."
Jerkass: Heenan ripped on the faces a lot while a commentator, but none so much as Tito Santana. Interestingly, Tito was actually one of Heenan's favorite wrestlers in real life, and Heenan's constant ripping of him was an attempt to garner fan support for him.
Red Baron: "Pretty Boy," "The Brain" (taken from Eddie Creatchman), "The Weasel" (imposed on him by The Crusher)
Shout-Out: After WrathSquashed Olympic bobsledder-turned-pro-wrestler Chip Minton on the December 3, 1998 episode of WCW Thunder, Heenan on commentary said, "So much for Rosebud."
Soft Water: Brought up at WCW Halloween Havoc 95, after Hulk Hogan pushed The Giant off the roof of Cobo Hall at the end of their Monster Truck challenge. Believing him to be dead from the fall, Bobby asked what side he fell into, river or street (with the implication being that falling into the water means finding his remains much more difficult). His commentary partners didn't see the difference. Cue Face Palm from Heenan.
Troll: This was pretty much his role on commentary in WCW, especially with Tony Schiavone, as he'd tell Blatant Lies or do anything he could think of to provoke/crack up/annoy him.
Unrelated Brothers: with Jerry Heenan, real name John Hill, who, among other names, also did this gimmick as "Gentleman" Jerry Valiant, with "Handsome" Jimmy Valiant (real name James Fanning) and "Luscious" Johnny Valiant (real name Thomas Sullivan), who weren't related to each other either.
Wounded Gazelle Gambit: While working for Dick the Bruiser's World Wrestling Association in Indianapolis in the 1960s, he once showed up for a match against "Cowboy" Bob Ellis on crutches, while pleading for a postponement (only four or five months!) Of course, Heenan "recovered" and tried attacking Ellis, who fought off both Heenan AND his Tag Teamthe Blackjacksby himself. Heenan took a bump over the top rope to the floor and got counted out while arguing with the commentators.