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.