John Belushi (died 1982) parodied Joe Cocker (died 2014). https://www.youtube.com/watch?v=aZsOyO_lXD8
Cliff Robertson (died in 2011) played Hugh Hefner (still alive) in Star 80.
I’m going to make an OP call, and say parodists don’t count.
As I expected, you all came up with a ton of examples, even though I couldn’t think of any. I’m sort of surprised how lopsided the male / female ratio is. Ruby Dee and Brittany Murphy are the only examples on the distaff side?
Everybody in the Star Trek movies.
Found another: Janet Brown (d. 2011) played Margaret Thatcher (d. 2013) in For Your Eyes Only (1981).
Philip Seymour Hoffman (died 2014) played Art Howe (still alive) in Moneyball.
Not sure if this counts, but in “Boys From Brazil,” the Laurence Olivier character is clearly supposed to be Simon Wiesenthal, who outlived Sir Larry.
One to keep an eye on: Frank Serpico may yet outlive Al Pacino.
Lindy “Dingos ate My Baby” Chamertlain is about the same age as Meryl Streep, and u but outlive her.
Lee Strasberg died a year before mobster Meyer Lansky, whom he sort of played in “Godfather Part 2.”
From All the President’s Men: Ben Bradlee (d.2014) outlived Jason Robards (d.2000)
However, Hal Holbrook (alive) did outlive Mark “Deep Throat” Felt (d.2008), and Redford/Hoffman vs. Woodward/Bernstein is still up for grabs.
A Farrah Fawcett two-fer: She died on June 25, 2009, eight years before Francine Hughes, whom she portrayed in the TV movie The Burning Bed. She also played the still living Elizabeth Diane Downes in the TV movie Small Sacrifices.
Brad Davis is dead, but Billy Hayes,the convict he played in the Turkish prison movie “Midnight Express,” is still alive.
American General “Jumping Jim” Gavin lived 17 years after the death of Robert Ryan, who played him in “The Longest Day.”
And Lieutenant Colonel Ben Vandervoort outlived John Wayne, who played him in that same movie.
Joseph Schildkraut died 16 years before Otto Frank (Anne’s father), whom he played in “The Diary of Anne Frank.”
Well, Vandervoort cheated by being born 10 years after Wayne, taking an unfair advantage!
Sidetrack: Really irks me when age-inappropriate actors are chosen for historical roles: Gavin was 37 on D-Day, Ryan was 53 in the film; Vandervoort was 27 on D-Day, Wayne was 55 in the film. Side-sidetrack: Although I guess I’ll give 30-year-old Audie Murphy a pass on portraying 19-year-old Audie Murphy in To Hell and Back (1955).
George Burns played the title role in “Oh God”. (Nietzsche might object).
And ever actor who ever played Jesus who died and stayed dead (though a lot of non-Christians might object).
George DiCertzo played Vincent Bugliosi in the TV movie Helter Skelter. DiCertzo died in 2010; Bugliosi in 2015.
A Bridge Too Far got it right with Gavin (Ryan O’Neal was 36) but went horribly wrong with others like 41 year ol Redford playing a 28 year old.