He's a dude playing a dude playing a dude disguised as another dude!

In Tropic Thunder Robert Downey plays an Australian actor playing the role of a black soldier. And at one point the black soldier disguises himself as a Vietnamese peasant. That’s 3 layers of character all at once:

Downey --> Australian actor --> black soldier --> Vietnamese peasant

Can anyone think of any other actors who have played 3 layers of character simultaneously? Has anyone ever done 4?

(Note – I’m not talking about actors who play different characters in different scenes like Peter Sellers did in Doctor Strangelove. I’m only talking about actors who play characters pretending to be other characters.)

Julie Andrews in Victor Victoria

Let’s see…

Julie Andrews --> Victoria Grant --> Count Victor Grezinski—> female cabaret singer

I can think of **Vincent D’Onofrio ** in Men in Black, who played a country bumpkin, Edgar, who got eaten by an alien bug who kept the ‘Edgar suit’ for the rest of the movie.
So Vincent’s a guy playing a bug playing a guy.

A man playing a woman playing a horse playing a broomstick.

Family Guy episode Fifteen Minutes of Shame. The guest before the Griffins on the Diane Show.

That’s probably cheating though. :smiley:

I’d guess that somewhere in the Mission: Impossible TV series that it happens (possibly more than once), but I can’t recall a particular instance at the moment.

There’s always Victor Victoria, but that kind of goes 'round and 'round.
In Bowfinger, Eddie Murphy –> ‘Jiff’ Ramsey –> Kit Ramsey –> <character in movie-within-a-movie>

Fool of a Took! It was a BROOMSTICK playing a HORSE playing a WOMAN playing a MAN!

You’re right, I got it backwards. I’ll give myself fifty lashes with a whip covered in bees with lasers surgically implanted on their backs.

Actually, don’t you have that backwards? Wasn’t it a broom playing a horse playing a woman playing a man?

I seem to remember a skit from a sketch comedy show, probably Kids in the Hall, where they were playing women who were pretending to be men pretending to be women. That was one messed up bit.

In Cypher:

(Really big spoilers underneath)

Jeremy Northam plays the role of Sebastian Rook, who has brainwashed himself into believing he is Morgan Sullivan, who then pretends to have been brainwashed into believing he is Jack Thursby.

I can’t believe no one’s mentioned “Victoria, Victoria” yet!

Since the OP didn’t explicitly exclude stage plays: In the original run of “As You Like It,” you would have had a boy playing a woman (Rosalind) who, for much of the play, dresses as a boy (Ganymede) who, at one point, pretends to be a woman (Rosalind again).

I’ve always wanted to make a movie about a guy who is trying to make a mockumentary about a theater group putting on a production of “Noises Off.”

Let’s not forget Tootsie.

Dustin Hoffman>Michael Dorsey>Dorothy Michaels>Emily Kimberly

and at the big finish Emily Kimberly revealed herself to be Edward Kimberly.

So that’s four levels.

I played such a role once in a high-school play called Catch me if you Can (no relation to the Leo DiCaprio movie). My character was introduced as Fr. Flannagan, but was fairly quickly outed as “Bugsy”, a mobster who was part of a conspiracy to murder the main character in an insurance swindle. But at the climax of the play, it was revealed that the Mafia conspiracy didn’t actually exist; it was all part of a sting operation to scare the main character into confessing to the murder of his wife before the first act, and that “Bugsy” was actually the police deputy.

Enough about that, though. Another example to fit the OP is several of the roles in Man of La Mancha. You have an actor, who’s playing Cervantes, who’s presenting the story of Alonzo Quihano, who has the delusion that he’s the knight Don Quixote. The innkeeper/king, Aldonza/Dulcinea, and Dr. Carrasco/the Knight of the Mirrors all also reach that level of layers, though I can’t remember their names as prisoners on the same layer as Cervantes.

In the Buffy tVS episode “Dopplegangland,” Alyson Hannigan plays Willow Rosenberg and Evil Willow, and then plays Evil Willow pretending to be Willow and Willow pretending to be Evil Willow.

That’s only two levels deep, I grant you, but it’s two characters bifurcated two deep. Surely that counts for Honorable Mention.

The innkeeper/king’s “prisoner name” is The Governor, and the Doctor/Knight of the Mirrors is The Duke.

(I did a zillion performances of this show in dinner theater).

From the same show - how about This Year’s Girl, where Buffy and Faith switch bodies. So you have Eliza Dushku playing Faith, playing Buffy, playing Faith. And vice-versa.

There’s an episode of The Jeffersons in which (1) Sherman Hemsley and Isabel Sanford play (2) George and Weezie, of course; then, during a dream they both play (3) actors in stage play, portraying (4) Dr. and Mrs. Martin Luther King, Jr.

In Shakespeare in Love, Gwynneth Paltrow plays Viola De Lesseps, pretending to be Thomas Kent, who is playing Romeo.

(Oh, and in the play Romeo and Juliet, Romeo pretends to be a Montague ambassador, which would take things one level deeper.)