I don't know when the main text was written, but is Hillary Duff really a good example of a "larger than life" celebrity anymore?

Supernatural. *Especially* the season 6 episode, The French Mistake, where Sam and Dean are transported to a universe where they're the actors themselves. The actors are playing the characters who are in turn playing the actors in the "real world". The crew are all like "wtf is up with you two?"

On a related note: "Supernatural is filmed in front of a live studio audience" was the funniest opening ever. It ties in, at least thematically, to the whole 'Supernatural is a book series based on our lives' thread written (well, envisioned) by Chuck.

You either love it or hate it.

Very definitely a case of breaking the fourth wall, if the actor/crew/etc are mentioned.