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The Crazy Bet Matthew Perry Lost To Courteney Cox On Friends

The characters in "Friends" aren't afraid of putting their money — or their apartments and roosters — where their mouths are. In one of the best episodes of "Friends," Monica (Courteney Cox) and Rachel (Jennifer Aniston) lose a bet with Chandler (Matthew Perry) and Joey (Matt LeBlanc) that sees them trade their clean and spacious apartment for the boys' less-than-equivalent space. And it's all because neither of them know what Chandler's job was. Sorry, Rachel — Chandler's not a "transponster." That's not even a word!

Behind the scenes, the cast and crew of "Friends" also got into a few interesting bets of their own. Perry, in particular, is behind two of the most famous ones.

In a 2018 video interview with WIRED, Bruce Willis revealed that the real reason he agreed to guest star in "Friends" — for free — is because he lost a bet to Perry. According to Comic Book Resources, the bet came about when Willis and Perry were making the comedy movie "The Whole Nine Yards" together. The story goes that Perry bet against Willis that "The Whole Nine Yards" would open at No. 1. To many people's surprise, including Willis', it did. Willis later confirmed a version of this story to WIRED, and it's known that he donated what would have been his payment for his "Friends" cameo to various charities.

However, Courteney Cox has also revealed the existence of a different "Friends" bet — one in which Perry wasn't so fortunate.

Monica would have appreciated Courteney Cox's bet with Matthew Perry

Some time in the 4th year of "Friends," Courteney Cox appeared on an episode of "The Tonight Show with Jay Leno." She told Leno that she and Matthew Perry had gotten into a bet over which movie had included the Anthony Michael Hall line, "Chicks cannot hold their smoke. That's what it is."

Cox thought Hall said the line as Brian Johnson in "The Breakfast Club." Perry insisted it was when he'd played Gary Wallace in "Weird Science." Eventually, the rest of the "Friends" cast and crew took sides, and things escalated. This was the late '90s, so although they did try the internet — much to Leno's amusement — they couldn't find an answer. Cox said they were calling people and trying to find tapes of the movies to confirm who was right.

Meanwhile, the stakes between Cox and Perry were escalating too. It rose from a simple $20 bet to Perry making an indecent proposal (presumably not entirely seriously) that Cox politely turned down.

In the end, the debate was resolved in a very Hollywood way. The "Friends" team learned that Judd Nelson, who played Bender in "The Breakfast Club," was working on the sitcom "Suddenly Susan" on another Warner Bros. lot, so they went to him for help. Nelson confirmed that Cox was right: Hall's character said the line to Nelson's character in "The Breakfast Club."

So, what did Cox win? Perry had to wait on her every whim for at least five months — including answering to Cox ringing a bell and appearing at her side during the interview with Leno.

Did the offscreen bet inspire the quiz episode?

Time to play TV detective. The "Friends" episode featuring the apartment bet ("The One with All the Embryos") aired on January 15, 1998. In "The Tonight Show" episode when Courteney Cox told the bet anecdote, she mentioned that "Friends" was in its 4th year, which would put the date of that interview in 1998 since "Friends" first aired in 1994. But she might have meant its 4th season, which started on September 25, 1997 (via IMDb).

Per IMDb, Cox guested on "The Tonight Show" on November 6, 1997, in the middle of the 4th season of "Friends," and it was likely in that appearance that she told the story. Cox had also appeared on "The Tonight Show" in 1996, when "Friends" was in its 3rd season. 

It's unknown when exactly Cox's bet with Matthew Perry took place. But considering that Cox didn't tell the anecdote in 1996 and Perry still had five months of bet-induced servitude left by November 1997, one could hazard a guess (but no one's apartments) that the bet took place between the premieres of Seasons 3 and 4. "Friends" was filmed with a live studio audience a few months before reaching TV audiences, which means that depending on the terms of the bet, the writers would potentially have had time to incorporate the offscreen bet into the show.

Either way, it proves just how close — and competitive — the cast was in real life as well as while in character. That, and you shouldn't challenge Cox's "Breakfast Club" knowledge.