Raymond Louis Heenan was born in Chicago, Illinois, on November 1, 1944. Heenan dropped out of school in the eighth grade to support his mother and grandmother. As a fan of wrestling growing up in Chicago and Indianapolis, he started in the wrestling profession early on, carrying bags and jackets for the wrestlers, and selling refreshments at events.

In 1961, Heenan became a regular in William Afflis’ (known by his in-ring persona Dick the Bruiser) Indianapolis-based WWA promotion under the moniker “Pretty Boy” Bobby Heenan. That year, he wrestled his first match against Calvin “Prince” Pullins. Heenan said that he was never trained as a wrestler and that it came naturally to him. He was booked as both a manager and a wrestler after the promoters saw how well he handled the physical aspects of his managerial duties. During his time in WWA, he managed Angelo Poffo and Chris Markoff, the Assassins (Guy Mitchell and Joe Tomasso), The Valiant Brothers and The Blackjacks. In particular, Heenan was credited with making Blackjack Lanza one of the top wrestling villains in the country. This impressed promoter Sam Muchnick, who typically hated wrestling managers, and Heenan is believed to be the only heel manager to work in Muchnick’s St. Louis Wrestling Club. He also occasionally wrestled with a storyline “brother” Guy Heenan, portrayed by Guy Mitchell, from the Assassins. In 1974, he left the WWA. He attributed his departure to a dispute with Afflis over pay for his participation in the first-ever wrestling event held at Market Square Arena, emphatically stating that he never returned to the promotion as a result.

After leaving WWA, Heenan announced he was now to be known as “The Brain” at his AWA debut in 1969. He took up managing the team of Nick Bockwinkel and Ray “The Crippler” Stevens, a duo which won a third AWA World Tag Team Championship under his leadership. While Bockwinkel and Stevens feuded with The Crusher and Dick the Bruiser, Bruiser famously called Heenan “Weasel”; this led to his rivals calling him “Weasel” throughout the rest of his wrestling career. The AWA was the starting point for the first incarnation of his eponymous heel stable, The Heenan Family, which initially consisted of Bockwinkel, Stevens, Bobby Duncum Sr., and Blackjack Lanza.

On January 25, 1975, an angry fan fired a gun at Heenan in Chicago’s International Amphitheatre after Heenan interfered in one of Bockwinkel’s matches. Heenan was unharmed, but five people sitting ringside were injured, one of them critically. Later in 1975, Bockwinkel captured his first of several AWA World Heavyweight Championships, ending the seven-year reign of perennial champion and AWA promoter Verne Gagne. While Bockwinkel was AWA Champion in 1976, Lanza and Duncum captured the AWA World Tag Team Championship, making Heenan the first manager in history to simultaneously manage both a major promotion’s singles and tag team champions.

In early 1979, Heenan left the AWA (suspended one year, in storyline) to work in Georgia Championship Wrestling (GCW). During his short tenure in GCW, Heenan managed a stable of wrestlers that included the likes of Killer Karl Kox, Masked Superstar, Ernie Ladd and Blackjack Lanza. Heenan met a young Hulk Hogan while in Georgia and later told AWA promoter Verne Gagne that he should hire him. According to Heenan, he moved his family to Atlanta after being told by GCW promoter Ole Anderson that he could work for the promotion as long as he wanted, only to release him less than a year later. Anderson admitted to releasing him but denied promising him indefinite employment.

In late 1979, Heenan returned to AWA and resumed managing Nick Bockwinkel to renewed championship success, including against Hogan in 1983. During AWA’s tour of Japan in 1983, Heenan suffered a neck injury in a match with Atsushi Onita that would limit his in-ring ability going forward.

In 1984, Heenan left AWA to join the World Wrestling Federation (WWF). While most of the AWA talent left for the WWF during this time without giving proper notice (the AWA required departing talent to work a six-week notice for booking and syndication-based reasons, with most talent claiming that WWF promoter Vince McMahon paid them extra not to work out their notices with the AWA), only Heenan worked out his notice in good faith to the Gagne family. He was written out of AWA television when Wally Karbo announced on the September 28 AWA broadcast that Heenan had been suspended indefinitely by AWA President Stanley Blackburn for initiating a brawl with The Fabulous Ones.

Heenan was signed by the WWF in 1984 with the intention of him managing Jesse Ventura, however Ventura’s retirement due to blood clots in his lungs prevented this from happening. Instead, Heenan managed Big John Studd in his feud against André the Giant. Studd challenged André to a US$15,000 bodyslam match at the first WrestleMania, with the stipulation being that André would have to retire had he lost. André won the match and then took the bag with the $15,000 and started throwing it out to the crowd before Heenan snatched the bag.

Heenan also wrestled sporadically in his WWF run. In his in-ring debut at Madison Square Garden in November 1984, he pinned Salvatore Bellomo. Heenan’s most notable victory came at WrestleMania IV, teaming with The Islanders to defeat The British Bulldogs and Koko B. Ware. The following year, he was defeated in 30 seconds by former client The Red Rooster at WrestleMania V. Heenan also wrestled a series of “Weasel Suit matches” against The Ultimate Warrior, who defeated Heenan by forcing him into a weasel costume. His final in ring match came on August 2, 1991 at a house show in Long Island, New York, where he defeated Mr. Fuji.

In 1984, WWF owner Vince McMahon took full advantage of his microphone and comedic skills and Heenan became a color commentator in addition to his managing duties. He replaced Jesse Ventura on Prime Time Wrestling and All American Wrestling, aired on the USA Network, teaming up with Gorilla Monsoon. He also replaced Ventura to team up with Monsoon on the syndicated All-Star Wrestling, which was replaced in the fall of 1986 with Wrestling Challenge. Although the purpose of these shows were to summarize weekly WWF events, viewers tuned in to see Heenan and Monsoon’s interactions.

Heenan reformed the Heenan Family, which over the years in the WWF would include Studd, “Olympic Strong Man” Ken Patera, “Playboy” Buddy Rose, “Mr. Wonderful” Paul Orndorff, King Kong Bundy, André the Giant, High Chief Sivi Afi, the Brain Busters (former Four Horsemen members Arn Anderson and Tully Blanchard), “Ravishing” Rick Rude, “King” Harley Race, the Islanders (Haku and Tama), Hercules, The Barbarian, Mr. Perfect, The Red Rooster, and The Brooklyn Brawler. Heenan and the Heenan Family had a feud with Hulk Hogan in the 1980s, and Heenan managed two WrestleMania challengers to Hogan’s title. In 1986, Heenan managed King Kong Bundy in his main event bout at WrestleMania 2. During the André the Giant–Hulk Hogan rivalry preceding WrestleMania III, André sided with Heenan and challenged Hogan at the event. While neither Bundy nor André won the title at that time, André later bested Hogan for the championship on The Main Event I on February 5, 1988, in a controversial win after he aligned himself with “The Million Dollar Man” Ted DiBiase.

Heenan retired from managing in 1991 to become a full-time commentator. Nonetheless, Heenan crossed the line to managing sporadically. When the WWF signed Ric Flair, Heenan spent several weeks talking Flair up as “The Real World’s Heavyweight Champion”, appearing onscreen with Flair’s Big Gold Belt. He continued to act as an adviser to Flair during his WWF run from 1991 to 1993. Though he nominally managed Flair, Heenan’s former protégé Mr. Perfect, who temporarily retired due to injury, would regularly accompany Flair to ringside as his “Executive Consultant”. At the 1993 Royal Rumble, he introduced “The Narcissist” Lex Luger to the WWF to exact revenge on his former protégé, Mr. Perfect.

On January 27, 1994, Heenan made his debut in World Championship Wrestling (WCW). He was originally brought in to replace Jesse Ventura, his former client, as the color commentator for WCW Saturday Night and eventually took over Ventura’s position as the company’s lead commentator, replacing him for pay-per-view events and on the syndicated WCW Worldwide and Clash of the Champions events produced for TBS. When WCW Monday Nitro premiered in September 1995, Heenan left Saturday Night to work on the new show full-time and joined former Chicago Bears defensive lineman Steve McMichael as an analyst alongside play-by-play man Eric Bischoff. He was later frequently paired with Tony Schiavone.

Heenan made appearances as a guest on various television shows, including: Family Feud, Live with Regis and Kathie Lee, The Jerry Lewis MDA Labor Day Telethon, Nickelodeon Kids’ Choice Awards, The Arsenio Hall Show, and The Dennis Miller Show. He also made an appearance in the 1995 film Timemaster. Heenan had a parody talk show known as The Bobby Heenan Show, which was broadcast in four segments during the second half of WWF’s regular weekly program Prime Time Wrestling.

In 1996, Heenan made a one-off return to ringside at The Great American Bash as the manager of two of his former clients, Ric Flair and Arn Anderson, in a tag team match against his broadcast colleague McMichael and then-Carolina Panthers linebacker Kevin Greene. Heenan was instrumental in convincing McMichael to turn on his partner, which enabled Flair and Anderson to win the match, and fill the open spot in The Four Horsemen that Brian Pillman left behind when he departed the company earlier in the year.

Starting in late January 2000, WCW replaced Heenan on Monday Nitro and pay-per-view events with Mark Madden. Heenan continued to commentate on Thunder along with Mike Tenay, and later Schiavone, until he was replaced by Stevie Ray beginning in July 2000. Heenan was then only seen with Scott Hudson on Worldwide until he was released by WCW in November 2000. Heenan said he was uninspired in WCW due to the negative work environment and due to conflicts with Schiavone. WCW went out of business less than a year after his release.

On April 1, 2001, Heenan returned to the WWF and provided commentary to the Gimmick Battle Royal match at WrestleMania X-Seven alongside “Mean” Gene Okerlund. Heenan was inducted into the WWE Hall of Fame class of 2004 (WWF changed its name to WWE in 2002) by Blackjack Lanza. The following night, he appeared at WrestleMania XX in a skit with Gene Okerlund, Mae Young and The Fabulous Moolah. He inducted his protégés Paul Orndorff, The Blackjacks and Nick Bockwinkel into the WWE Hall of Fame class of 2005, class of 2006 and class of 2007 respectively. In his last WWE appearance, he was one of the speakers for “Mr McMahon appreciation night” on the June 11, 2007 episode of Raw.

Heenan made several appearances on the independent circuit. In February 2001, Heenan did color commentary for the WOW Unleashed pay-per-view. Also in 2001, Heenan worked briefly as a “sports agent” in the Xcitement Wrestling Federation with Curt Hennig under his tutelage. In 2004, he feuded with fellow manager Jim Cornette in Ring of Honor.

His first memoir, Bobby The Brain: Wrestling’s Bad Boy Tells All, was released by Triumph Books on September 1, 2002 with a foreword from Hulk Hogan. A second memoir, Chair Shots and Other Obstacles: Winning Life’s Wrestling Matches, was released by Sports Publishing on February 1, 2004 and has an introduction by Ric Flair. Both books were co-written by Steve Anderson.

In January 2002, Heenan announced that he had throat cancer. By 2004, the cancer had gone into remission. The treatments caused a great deal of weight loss, dramatically altering his appearance and voice.

In 2004, he joined former WCW commentators Tony Schiavone and Larry Zbyszko in providing commentary for the video game Showdown: Legends of Wrestling. After his Hall of Fame induction, Heenan provided comments for use in WWE documentary releases. In December 2010, WWE released a retrospective two-disc DVD on Heenan’s career titled WWE: Bobby “The Brain” Heenan.

Heenan made a series of appearances for Total Nonstop Action Wrestling (TNA) in December 2005, culminating at the Turning Point pay-per-view, where he provided commentary for the Six Man Tag Team Basebrawl match between The Diamonds in the Rough and Chris Sabin, Dale Torborg and Sonjay Dutt. His final appearance for TNA was on the September 7, 2006 episode of Impact!, when he appeared to make a bid to manage “free agent” Robert Roode.

In December 2007, Heenan had reconstructive surgery on his jaw, after the first surgery was unsuccessful. He was placed in a medically induced coma and was slowly brought out. In the second half of January 2008, he had come out of his medically induced coma. For a time, Heenan was unable to speak and had to communicate with his eyes. In December 2009, Heenan was hospitalized after an examination of his rebuilt jaw found an infection that needed to be treated.

Pro Wrestling Report honored Heenan at the annual Blizzard Brawl event on December 5, 2009, in Milwaukee, Wisconsin, as he was given their Lifetime Achievement Award. In addition to this, the mayor of Milwaukee, Tom Barrett, declared December 5, 2009, to be “Bobby Heenan Day”.

In the last few years of his life, he suffered a series of falls. In 2010, he broke a hip and his shoulder in a fall that also fractured his pelvis. He fell out of bed and broke a shoulder in April 2014. In May 2016, he fell again and broke a hip.

Heenan is considered by many to be the greatest wrestling manager of all time, including WWE, who placed him at the top of their 25 greatest managers list in 2011. The Post and Courier columnist Mike Mooneyham said Heenan became a blueprint for managers and fellow manager Jim Cornette said: “He formed in my mind as a fan and performer what I thought a manager should be.” Author Brian Shields notes that many consider him “one of the most significant figures in professional wrestling history”. For his work in promoting André the Giant’s match with Hulk Hogan at WrestleMania III, often cited as the most famous American professional wrestling match, Heenan received a six-figure payoff—arguably the largest pay day in any managerial career. Broadcaster Peter Rosenberg considers Heenan a personal hero and describes him as the best commentator, manager and bad guy in WWE history. Rosenberg stated that Heenan “operated on multiple levels”, adding: “If you were a little kid, he was the foil to your hero. As an adult, you look back and appreciate just how much of a comedic genius he was.”

On September 17, 2017, Heenan died at the age of 72 while surrounded by family at his home in Largo, Florida. His cause of death was organ failure due to complications from the throat cancer that had been in remission since 2004.