Conversation so far:
What media appearances did flavor make?
In 2002, Flav appeared in Taking Back Sunday's music video for their song You're So Last Summer.
did he appear on tv shows as well?
2005, Flav took part in the UK reality TV show The Farm on Channel 5.
What was his role on the Farm?
CANNOTANSWER.
did he star with anybody?
Flavor Flav made a guest appearance in the animated sitcom The Simpsons as himself, in the episode Pranksta Rap.

Question: what year was that?
Self-contained rewrite: what year did Flavor Flav make a guest appearance in the animated sitcom The Simpsons as himself