Bobby “The Brain” Heenan—one of the funniest, most annoying, and inarguably greatest characters professional wrestling has ever produced—died yesterday afternoon at the age of 73. A cause of death was not announced, but Heenan had been suffering from a host of ailments since he was diagnosed with throat cancer in 2002. Born Raymond Louis Heenan in 1944, Heenan dropped out of school to support his family, and found his calling in the professional wrestling business working for Midwestern promotions like the World Wrestling Association and American Wrestling Association. Heenan was known as a “heel manager”—in wrestling parlance, the mouthpiece of the bad guy wrestlers.

Heenan’s most famous run would be with the WWF, where he managed Andre the Giant during his 1987 feud with Hulk Hogan. The buildup to their championship match at WrestleMania III remains one of the greatest storylines in professional wrestling history, from Andre signaling his heel turn by ripping the shirt and crucifix off of Hogan, to Andre throwing Hogan over the top rope at the Saturday Night Main Event battle royal, to the sight of Hogan body slamming Andre and scoring the pin at WrestleMania. Throughout the build, it would be Heenan who would antagonize Hogan, then at the height of his popularity.

Neck injuries would later force Heenan out of in-ring managing, and he found new life as an on-air color commentator. As the loud-mouthed foil to WWF play-by-play announcer Gorilla Monsoon, the pair would be the voices behind some of the late ‘80s’ and early ‘90s’ most iconic matches, including what’s regarded as Heenan’s best performance, his commentary during the 1992 Royal Rumble. This would be the match where Ric Flair—once managed by Heenan—would eliminate Sid Justice (with help from Hogan) to win the WWF championship. Heenan’s “Yes! Yes! Yes! Yes! Yes! I told you! I told you!” added the exclamation point to one of the best Royal Rumble matches in history.

After Vince McMahon decided against renewing his contract in 1993, Heenan left the WWF to rival WCW, where he was the voice during WCW’s great mid-’90s run, providing the soundtrack to Hulk Hogan joining the N.W.O. and to Goldberg winning the WCW heavyweight championship.

After Heenan was diagnosed with throat cancer in 2002, he largely stayed out of wrestling. In 2004, Heenan was inducted into the WWE Hall of Fame, but by then his voice and speech were betraying him. Reconstructive surgery on his jaw a decade ago left him largely unable to talk, a tragic and ironic coda given Heenan’s standing as pro wrestling’s greatest loudmouth.