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The Simpsons has been on the air for over 30 years. In that time it has become known for frequently casting celebrities in guest roles. Many of these celebrities play themselves, or their characters resemble the actors voicing them1. In the time that The Simpsons has been on the air has a celebrity made multiple guest appearances where a) their on-screen likeness is modeled after their actual physical appearance and b) the likeness of the character has changed between episodes, reflecting the aging of the celebrity in the real world between appearances on the show?

1 ex: David Duchovny and Gillian Anderson voice Mulder and Scully respectively in "The Springfield Files". They do not technically play themselves, but the characters look like the actors voicing them.

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    I suppose one could claim that any actor who has died later appeared as a skeleton in a Treehouse of Terror, in an unannounced cameo....
    – RDFozz
    Commented Feb 18, 2021 at 18:35
  • No one in the Simpsons world ages (Bart and Lisa have been kids for 30+ years).
    – MissouriSpartan
    Commented Feb 20, 2021 at 4:43
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    @MissouriSpartan That's the point of the question. Fictional characters don't age in the show but do characters based on real people?
    – Mike S
    Commented Feb 22, 2021 at 14:47

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It seems one example would be none other than Matt Groening himself.

The first time he appears in the Simpsons is Season 15, Episode 17 "My Big Fat Geek Wedding". He's a guest at the Bi-Mon-Sci-Fi-Con. He's very eagerly meeting his fans, signing autographs, gifting drawings, giving people snippets of his hair:

Picture of Simpson-ified Gr

He appears again in Season 21, Episode 1 "Homer the Whopper" filling up the back of a truck with Bongo comics mumbling "I'm so rich".

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He then re-appears in Season 32, Episode 7 "Three Dreams Denied" as a background character. Although this wasn't a speaking appearance.

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The appearance in My Big Fat Greek Wedding was the only reference I could find where he has brown hair. Ever since then they have depicted him as grey. Curiously, the promotional image for My Big Fat Greek Wedding shows him as grey (although I can't confirm this is actually an original promotional image from 2004. I just found it with the title "promotional image").

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