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Hugh Hefner was largely known for building the Playboy empire and throwing wild parties at his mansion.

Since the ‘60s, he was involved in Hollywood and beyond, and his party guests came from all backgrounds. It’s no secret that Hefner welcomed an astonishing amount of celebrities into his Playboy clubs and home, and among them was Bill Cosby.

Many know that already. During one of Cosby’s visits to Hefner’s compound, he and another comedian got into a heated fight and Hefner stepped in.

Hugh Hefner, Bill Cosby
Hugh Hefner | Hector Mata/AFP via Getty Images; Bill Cosby | M. Von Holden/FilmMagic for The Thelonious Monk Institute of Jazz

Who did Cosby fight?

Back in the late ‘60s, the popular Smothers Brothers had their own comedy variety series that aired on CBS. It was cancelled by the network because some of its content—which was anti-war, etc.—was considered too controversial.

Tom and Dick Smothers worked in music and acting after that, but Tom became increasingly more vocal about his political beliefs.

He and Cosby had an especially tense moment when Cosby was a guest host on The Tonight Show and they traded barbs. Outside of TV, Smothers scolded Cosby for not being outspoken about civil rights. That’s where the mutual dislike began. Things escalated at Hefner’s home.

Bill Cosby hit Tom Smothers at a party

One night in 1976, Hefner hosted a watch party for the Muhammad Ali vs. Ken Norton fight. His California mansion was full of celebrity guests, including Cosby and Smothers. The pair were not on good terms.

According to the book, Seriously Funny: The Rebel Comedians of the 1950s and 1960s, Smothers said this about Cosby: “At the time I was very volatile, and thought everyone should take a stand. I guess I said something that really pissed him [off]. For a couple years after that, I’d say, ‘Hiya Bill, how ya doing?’”

Smothers’ version of the fight stated he congratulated Cosby on his new TV show, not knowing it was recently canceled. He then told Cosby he liked it and “It as a good effort.” Cosby—who took it as a backhanded compliment—didn’t say anything but glared at Smothers.

That prompted Smothers to say “F**k you.” He said he turned around and walked away and that’s when Cosby punched him, knocking him to the floor.

“He hit me right in the head with his fist – knocked me down … and I was down there a minute or two and he was standing over me screaming at me, ‘C’mon, I’ll kick your ass,’ stuff like that. I’ve never seen him since then.”

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But Cosby’s people had a different account. Cosby’s secretary said Smothers was taunting Cosby all evening. She said, “The man was warned twice. Mr. Cosby did ask him twice not to mess with him, so it wasn’t just a ‘fly off the handle’ thing.”

Hugh Hefner broke up the brawl

Smothers said that Cosby maneuvered himself around Hefner to knock him one, and it came off as sneaky. But ultimately, Hefner stepped in to break up the fight.

He refused to comment to the media, but with so many people crowded in his house that night, word soon got around the gossip circuit. Cosby was embarrassed by the situation, but he and Smothers never resolved their differences.