He began as a wrestler in the late 1970s as Pretty Boy Heenan but soon realized his niche was in managing and he quickly took on the contract of AWA Champion Nick Bockwinkle, Ray Stevens, Ken Patera and Bobby Duncam to wage war with Vergne Gagne, Sgt. Slaughter and other AWA favourites as well as Andre the GIant and Hulk Hogan. Heenan was in Nick Bockwinkel's corner when he lost the AWA World Heavyweight Title to Hulk Hogan in a match decision that was overturned just days later, leading to Hogan's decision to quit the company. Heenan would follow soon after.

    Heenan joined Vince McMahon's World Wrestling Federation originally to manage Jesse "The Body" Ventura, however, Jesse Ventura was forced into retirement soon after Heenan's WWF debut. Bobby Heenan was instead paired with Big John Studd and it would be a history making union as Studd challenged Andre the Giant in a wild feud culminating in the $15,000 Slam Match at Wrestlemania I which Andre won. After the match, Heenan stole back the $15,000 and re-earned the nick-name "The Weasel". Bobby Heenan would quickly re-establish the Heenan Family, adding King Kong Bundy, Hercules Hernandez, Harley Race, the Fabulous Moolah and Paul Orndorff to the fold at various times, but his biggest acquisition would come in the form of the over 500 pound Andre the Giant just prior to Wrestlemania III.

    Heenan was in the corner of the Giant when he was picked up and slammed by Hulk Hogan in the Pontiac Silverdome in front of 93,173 fans and would spend the rest of his managerial career trying to destroy Hulkamania. Heenan managed Andre after a brief break from wrestling and also began managing Haku and Tama, the Islanders, against the British Bulldogs, culminating in a six man tag team match at Wrestlemania IV as Heenan and the Islanders defeated the Bulldogs and Koko B. Ware. Heenan briefly sold the contract of Andre the Giant to Ted DiBiase and thus was not in his corner for his WWF World Title win in February of 1988, though Heenan was back with Andre for Summer Slam 1988 as he teamed with Ted DiBiase against Hulk Hogan and Randy Savage.

    Andre the Giant brought in new talent like Ravishing Rick Rude and also the former Horsemen members Arn Anderson and Tully Blanchard. Heenan got his first taste of WWF gold at Wrestlemania V when Rick Rude pinned the Ultimate Warrior to win the WWF Intercontinental Title and just prior to Summer Slam in 1989, Heenan lead Anderson and Blanchard, as the Brain Busters, to the WWF World Tag Team Titles over Ax and Smash of Demolition. The Heenan Family was holding 2 out of the 3 recognized WWF championships but it wouldn't last long as all the gold went back to their original holders. Heenan wrestled on two WWF pay-per-views in 1989, first losing to the Red Rooster at Wrestlemania V and then being eliminated by the Ultimate Warrior at the 1989 Survivor Series. Heenan was able to bring gold back to the Heenan Family when he lead Andre the Giant and Haku, as the Colossal Connection, to the WWF World Tag Team Titles in December of 1989 and they would hold the titles until Wrestlemania VI. After the match, Heenan slapped the Giant and was beaten up for his efforts.

    Heenan regrouped and brought the Barbarian into Heenan Family and would also later add Mr. Perfect Curt Hennig to the fold when Heenan interfered in the finals of a tournament to crown a new WWF Intercontinental Champion. Heenan and Perfect were the PERFECT pair with great chemistry. Heenan lead Perfect into main event feuds with WWF Champion the Ultimate Warrior and Hulk Hogan. Perfect briefly traded the title with Kerry von Erich and then went on to feud with the Big Bossman on behalf of his manager with the Bossman defeating Perfect by disqualification at Wrestlemania VII.

    In the summer of 1991, the World Wrestling Federation scored a coup by signing the reigning NWA/WCW World Heavyweight Champion, the "Nature Boy" Ric Flair. Heenan had announced his retirement from managing so that he could focus on broadcasting, though the return of Flair brought Heenan back to ringside briefly. Heenan later said he couldn't handle the Ric Flair schedule of partying and actually threatened to quit the WWF if he wasn't allowed to go back to the broadcast booth. When Mr. Perfect fell to a back injury, Heenan took a position as Ric Flair's "Financial Advisor" while Mr. Perfect served as the ringside manager, though he used the title "Executive Consultant". Heenan would celebrate with Ric Flair and Mr. Perfect after Flair won the 1992 Royal Rumble and was instrumental in pushing Flair as the WWF's top heel attraction from the broadcast booth. Heenan would enjoy a great run with Gorilla Monsoon on WWF pay per views and also formed successful broadcast teams with Vince McMahon and Jim Ross. When Mr. Perfect turned his back on Flair and joined forces with the Macho Man, Heenan went berzerk and in storyline terms started to go a little loopy. He unveiled Lex Luger as the Narcissist at the 1993 Royal Rumble and began focusing on Luger from the broadcast booth as Flair returned to WCW. When Lex Luger turned into a fan favourite in the summer of 1993, Heenan was truly and officially out of managing and soon left the World Wrestling Federation to join Ted Turner's WCW after a contract dispute.

    Heenan showed up at the Clash of the Champions to join Tony Schiavonie and WWF alumnus Mean Gene Okerlund as the major players of the WCW broadcast team. Heenan dropped the "F-bomb" on his first night when Brian Pillman grabbed him at ringside. Heenan, having had a history of serious neck problems, was legitimately upset and fearful and quickly apologized for his words and nothing came of it. Heenan didn't enjoy his time in WCW, though he was reunited with Ric Flair and Arn Anderson at the 1996 Great American Bash in a one-night-only managerial spot. Heenan would continue on with WCW but was replaced during the Russo era by Mark Madden.

    When WCW closed in 2001, Heenan and Mean Gene were free to return to the World Wrestling Federation and appeared at Wrestlemania XVII as the special broadcast team for the Gimmick Battle Royal. Heenan soon after met with tragedy as he was diagnosed with throat cancer. With wit and the same determination that made him a household name, Heenan beat that opponent and was added to the WWF Hall of Fame in 2004. Heenan also lends his name to the independent scene in the US managing various upstarts and legends alike but usually in main events. Heenan even has a new feud of sorts going with Jim Cornette! He's always up to something and hopefully will stay that way forever! Bobby Heenan... the Brain.... the man who spoke to the "humanoids" and told them the way it was.... congratulations! You belong in the Hall of Fame not only as the manager of champions but for what you always said you'd be: the Walter Cronkite of Professional Wrestling. Well... not quite, but thank you for being the FIRST and ONLY Bobby Heenan.