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I vote 88 Minutes and Righteous Kill...both Pacino flicks in 2008 that would fit quite nicely into the "has-been actor wishes he was still the edgy, brilliant young actor that he was" category.
not a movie, but studio 60 on the sunset strip and 30 rock come to mind.
Great Point, Anonymous - on the Like Father, Like Son and Vice Versa link (about a half-year apart). That one all depends on how you like your small-screen to silver screen child actors (for my money Fred Savage>Kirk Cameron) - and for that matter the fathers in that movie (Dudley Moore vs. Judge Reinhold). Tough Call.
LADYDI: You forgot to mention an 80's classic - 18 Again! with the late, great George Burns! Knowing that Zac Efron is going to be playing an old man in his pre-pubescent body probably has old Burnsy spinnin' in his grave.
Independence Day and Mars Attacks!.