I just saw a production of “I Hate Hamlet” where the main character is playing guess who.
In the movie of Tristram Shandy the main characters play themselves making a movie of Tristram Shandy.Which is appropriate, since the book was about writing the book.
There’s also Galaxy Quest, where the main cast members play actors who portray the fictional crew of a starship.
Snoopy played a whole bunch of fictional characters–the World War 1 Flying Ace, Joe Cool, etc. Does he count?
Or Paul Giamatti playing Bob Zmuda pretending to be Andy Kaufman pretending to be Tony Clifton?
Daffy Duck plays Duck Dodgers, in the immortal classic “Duck Dodgers in the 24 1/2 Century.”
If I’m reading the OP correctly, Will Smith role plays a character who’s really Paul, but pretends for most of the film to the be the son of Sidney Potier.
Dead Poets’ Society features one of its characters starring in a production of A Midsummer Night’s Dream.
In The Sixth Sense, the character Cole plays a fictionalized King Arthur in a school play.
Charlton Heston portrays the lead actor portraying the king in the play within the play in Branagh’s Hamlet. (There are other actors playing actors playing roles too of course, but not as famous.)
Emma Thompson and Laurie Metcalf both played the fictional character of Frasier’s ex-wife Ann who makes her living playing Nanny G, a children’s singer. One of the greatest episodes of Frasier featured Derek Jacoby as fictional Jackson Hedley, an appallingly bad Shakespearean actor who portrays several Shakespearean characters in a one man show.
Mark Indelicato plays fictional Justin on Ugly Betty who portrayed fictional Tony in a school production of West Side Story.
Fictional director Lionel DeBris portrays a fictionalized Hitler in The Producers. (Hitler was a real person of course, but probably not quite as good a dancer.)
I once played such a role in a high school play. The character was listed as Father Flannerty (at least, I think that was the last name), but as the play developed, the kind-hearted priest was revealed to be a cover identity for a mobster named “Bugsy”. And as it further developed, “Bugsy” wasn’t a mobster after all, but the sherrif’s deputy, engaged in an elaborate scheme to scare a confession out of a murderer.
There are also a few examples of a three-deep (four layers total, including the actor) in Man of La Mancha: Actor -> Cervantes -> Alonzo Quihano -> Don Quixote, plus Dulcinea, the King, and the Knight of the Mirrors, who also existed on those same levels.
Besides the fact that I messed up the typing on this post, I meant to add that Sidney Poitier doesn’t have a son in real life – he has six daughthers, which is why impersonating his son would be playing a fictional character.
Nitpick: Dorothy Michaels played Miss Emily Kimberly, the new hospital administrator (on Southwest General).
And the actors portraying George, Kramer and Elaine on “Jerry” were actors portraying fictional characters portraying fictional characters.
Nit-nitpick: actually, she played Edward Kimberly, the long-lost brother of Emily, as the final shocking reveal… eh… revealed.
Homer was Poochy.
Several actors have played Superman, who played Clark Kent. In Hollywoodland, Ben Affleck plays George Reeves, who plays Superman, who plays Clark Kent.
Or the entire TV Series “The Pretender”
Well, if you are going to bring secret identities into the equation, we’ll be here all night:
Anyone who has played Supergirl/Kara/Linda Lee
Anyone who has played Superman/Clark Kent/Kal-El
Anyone who has played Batman/Bruce Wayne
Anyone who has played Spiderman/Peter Parker
et al, etc, ad naseum
It might also help if I mention the movie was Six Degrees of Separation. :smack:
Rip Tide, Gotta Dance
And just to confuse it, don’t forget that Dr. Johnny Fever was merely a persona played by John Caravella, played by Howard Hesseman.
Which I guess makes this as good a place as any to bring up Tim Reid playing Gordon Sims playing Venus Flytrap.
Don’t know if this counts for 3 deep or not, but in the Phantom of the Opera, the Phantom pretends to be an actor he just killed (Piangi?) who was playing the role of Don Juan.