My favorite quote from Stargate SG-1
“I’m Christian Bocher, portraying the character of Raymond Gunn, who portrays the character of Dr. Levant, which is based on the character Daniel Jackson portrayed by the actor Michael Shanks, originally portrayed by the actor James Spader in the feature film”
Shakespeare In Love
Gwyneth Paltrow plays Viola De Lesseps, pretending to be Thomas Kent, playing Romeo.
In the movie Sleuth, Michael Caine plays Milo Tindle, who in the course of his revenge against Laurence Olivier, pretends to be Police Inspector Plodder.
The imdb entry lists an actor other than Michael Caine for the part of Plodder, but his name was made up to not give away the surprise to the audience, as the credits are shown at the start of the movie. The birth date listed for him on imdb is April Fools’ Day of the same year Caine was born. In fact, though imdb.com lists six actors in the film, only Caine and Olivier actually exist and appear onscreen.
So does that make the current record 4 deep?
In the movie Sleuth the titular detective is played by Alec Cawthorne … who doesn’t actually exist.
(I trust a 35 year old movie doesn’t require a spoiler box)
There was a cartoon a while back where Superman pretended to be Batman after Batman vanished.
I liked the scene where he tossed aside a huge statue that Bane tossed onto him, while all the Batman villains gaped at him. Robin : “Ahh - he’s been working out.” * makes pumping iron motions *
Menocchio beat me to it – but I was going to say: The Muppets have parodied and played fictional characters, as have many animated characters from Bugs Bunny to Bart Simpson.
This is an “extra feature” since it aired after an unrelated episode, but here on Instant Star Jude Harris (Alexz Johnson) plays a femme fatale and Tommy Q (Tim Rozon) plays a gumshoe detective. It’s cute 
And this past season of Supernatural featured an actress who played “herself,” an actress who supposedly appeared in several recent horror movies (Ghostship, Boogeyman etc). I caught on when they got to movies I’d seen and knew she wasn’t in them.
Larry Pennell played Dash Riprock, an actor employed by Mammoth Studios. It’s unclear what roles were played by actor Riprock.
Also, you may remember Troy McClure from his many memorable performances.
I just thought of another one: in “Hannah Montana,” Miley Cyrus plays a girl named Miley Stewart, whose alter ego is pop singer Hannah Montana.
Yeah, *you *try ignoring the little brat and having a daughter who goes to elementary school at the same time, at least in the States.
I sure do! http://www.snpp.com/guides/troy.mcclure.html
Alec Guiness playing Obi Wan Kenobi playing Ben Kenobi.
You could throw in Anthony Hopkins playing Hannibal the Cannibal playing Dr. Lechter.