Bart Simpson encountered Sideshow Bob while visiting Cheers, years before The Simpsons even started airing. Believe it or not, the epic meeting took place way back in season four of the famous sitcom set in a bar.
“Diane’s Nightmare“, which aired on Halloween night in 1985, the future Bart Simpson and Sideshow Bob crossed paths. In this episode, Diane (Shelly Long) is confronted by the release of “Andy Andy”, a former Cheers patron, from prison. In a previous episode, Andy Andy nearly strangled Diane to death.
The show kicks off with Diane having an eerie nightmare and seeking solace from Frasier (Kelsey Grammer). He reassures her that Andy Andy, with whom he has secretly been counseling, has shown progress since his release from prison.
Diane refuses to meet her would-be killer, but Andy Andy arrives at the bar. He apologizes and promises to leave the country, admitting to telling “tiny fibs” to his fiancée Cynthia about his past. When Cynthia joins him at the bar, the Cheers gang pretends that Sam (Ted Danson) is the ex-con “flasher” employee, Diane is the desperate ex-girlfriend, and Frasier is the unhinged kleptomaniac.
The Iconic Moment Bart Simpson Meets Sideshow Bob on ‘Cheers’
Cheers fans with good memories and even better hearing might notice a familiar ring to Cynthia’s voice. She’s played by none other than Nacy Cartwright, the voice of Bart Simpson, and many other characters on The Simpsons. This Cheers appearance was a full year before she would be cast as Bart Simpson for The Tracy Ullman Show.
What makes Cartwright’s role on Cheers really hit home is a moment she shares with Kelsey Grammer. Andy Andy introduces Cynthia directly to the good doctor Frasier Crane, and the two shake hands.
Of course, Grammer would go on to play the recurring role of Sideshow Bob on The Simpsons. Sideshow Bob, originally Krusty the Clown’s sidekick, framed his abusive employer for armed robbery in “Krusty Gets Busted”. However, Bart Simpson foiled his plan, leading to Bob’s imprisonment. Seeking revenge, Bob and Bart became fierce enemies. Episodes featuring Grammer as Sideshow Bob are essentially a yearly tradition.
Most of the Cheers cast, including Grammer as Sideshow Bob, has appeared on The Simpsons. This makes sense, considering producer Sam Simon famously worked on both series. However, Nancy Cartwright is the only one of The Simpsons‘ six main cast members to have appeared on Cheers.
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