In 2000, you could see Logan Lerman as the young version of Mel Gibson’s character in WHAT WOMEN WANT, and Gibson and Lerman as father and son in THE PATRIOT.
In a film from 1939 called Tower of London, Basil Rathbone played Richard III, and Vincent Price played the Duke of Clarence. Later, in 1962, Vincent Price would play Richard III in a movie also called Tower of London, but with a different script.
Fredric March played Dr. Jekyll & Mr. Hyde in 1931 for Paramount. 10 years later, MGM remade the film (almost identical script) with Spencer Tracy in the title role, and then, in 1960, both March and Tracy starred in Inherit the Wind.
Lon Chaney, jr. played the monster in The Ghost of Frankenstein; Bela Lugosi played the monster in* Frankenstein meets the Wolfman*, and the two of them were both werewolves in the original The Wolf Man.
There was so much crossover in the Universal horror films, with Lugosi playing the Frankenstein monster at least once, and Dracula a couple of times, John Carradine playing Dracula once, and a mad doctor a couple of time, Boris Karloff playing the monster twice, and a mad doctor several time, Lon Chaney, jr. doing turns as the monster, the Wolfman, and Dracula, Glenn Strange showing up as the monster a couple of times, and Lionel Atwill and Dwight Frye playing burgomeisters and assistants in just about every film, plus Abbot and Costello meeting each monster at least once, I’m sure that at the very least, half of the Universal horror films could satisfy this.
Many TV shows that were made into movies featured cameos by the former actors.
For instance, Ann B. Davis and Florence Henderson (and few of the original kids) were in the Brady Bunch movies in the 1990’s.
Patrick Stewart and James MacAvoy both played Professor Charles Xavier; they both voice characters in Gnomeo and Juliet.
There are lots of cases of the original star appearing as a cameo in a remake or something with the same character.
So Victor Mature appeared as Samson in the 1949 Samson and Delilah and as Manoah in the 1984 TV movie Samson and Delilah, where Antony Hamilton played Samson.
Or Buster Crabbe who played both Flash Gordon (in the 1936 Flash Gordon and two sequels) and Buck Rogers (in the 1939 Buck Rogers), then appeared as “Brigadier Gordon” in the TV series Buck Rogers in the 25th Century, with Gil Gerard playing Buck Rogers.
Or James Garner, who played Bret Maverick in the TV series Maverick appearing in the movie Maverick in a more-than-cameo role as “Marshall Zane Cooper” alongside Mel Gibson’s Brett Maverick.
There are lots of other examples.
TV, not movie, but…
William Shatner and John Lithgow both played the protagonist of the Twilight Zone Episode Nightmare at 20,000 feet; Shatner in the original series and Lithgow in the 1983 movie.
Both appeared in an episode of Third Rock from the Sun where they comment on both of them having the same experience on a flight (the experience being the events of Nightmare at 20,000 feet)
Bebe Daniels and Mary Astor both played versions of Ruth Wonderly/Bridgid O’Shaughnessy in The Maltese Falcon and appeared together earlier in the silent film Unguarded Woman.
Bette Davis played the same role with a different name in Satan Met a Lady and appeared with Astor in The Great Lie
Noel Neill and Phyllis Coates (who both played Lois Lane) appeared in Invasion USA, though Neill was only a bit player.
Fess Parker, Arthur Hunnicutt, & John Wayne all portrayed Davy Crockett.
Fess Parker had an uncredited role in Island in the Sky starring John Wayne.
Arthur Hunnicutt appears with John Wayne in El Dorado.
Cate Blanchett (Elizabeth) and Judy Dench (Shakespeare in Love) both played Queen Elizabeth I.
They appeared together in Notes on a Scandal.
Sorry, I don’t think this counts, since the two Twilight Zone characters have different names, and thus can reasonably be construed as different people.
Anything in the James Bond arena? Don’t have time to look myself right now…
David Niven (Casino Royale) & Roger Moore in Escape to Athena.
Quite. Miriam Hopkins played 1/3 of the straight love triangle in the Hays Code-safe version of the play The Children’s Hour, called These Three. When the same director finally got a chance to make the play as it was into a movie, with the lesbian angle intact, Miriam Hopkins had a supporting role that was more than a cameo.
Faye Dunaway and Rene Russo both played insurance investigator Catherine Banning in the 1968 and 1999 versions of “The Thomas Crowne Affair.” Dunaway appeared in the '99 version as Pierce Brosnan’s therapist. Does that count?
Oh, also, Joan Hickson had a role in one of the Margaret Rutherford “Miss Marple” movies (Murder, She Said) from the 1960s, then, in the 1980s, Hickson would go on to play Marple herself for the series that I think was done by the BBC; it aired on US TV on Masterpiece Mystery.
More cameos:
Terry Moore played Jill Young in the original 1949 Mighty Joe Young and appeared in the 1999 version (still looking great fifty years later) with Charlize Theron playing Jill Young…
(Peter Jackson, by the way, desp[erately wanted Fay Wray to appear in his 2005 remake of King Kong, but she died before the production got started)
Kirk Alyn and Noel Neill, who played Superman and Lois Lane, respectively, in the 1948 serial Superman and its sequel, appear5ed in a cameo as Lois Lane’s mother and father in the train that Superman-as-a-boy (played by Jeff East) goes zipping by in the 1978 movie Superman, which starred Christopher Reeve and Margot Kidder as Superman and Lois. Noel also played Lois on the TV series Adventures of Superman from the second to the last season.
May McAvoy, who played Esther in the 1925 Ben Hur, also had a cameo in the 1959 remake (in a crowd) In 1959, Haya Harareet played Esther.
Hairspray , the 2007 musical, has two cameos from the original 1988 film. Ricki Lake, the original Tracy Turnblad, is in the audience in the musical. Nikki Blonski is Tracy in 2007. Jerry Stiller, the original Wilbur Turnblad, is Mr. Pinky in the musical. Alan Wendl is Mr. Pinky in 1988, and Christopher Walken is Wiulbur Turnblad in 2007
The 1998 movie Lost in Space has four cameos – Mark Goddard (the original Major Don West) plays a General, June Lockhart (Maureen “Mom” Robinson) plays a principal, and Marta Kristen and Angela Cartwright (Judy and Penny Robinson) play reporters. The new actors in the roles were Matt leBlanc (playing it serious), Mimi Rogers, Heather Graham, and Lacey Chabert
Hal Holbrook & Sam Waterston both played Abraham Lincoln & appeared in Capricorn One.
Did they appear in a movie together?
So have any of the various Batmen worked together?
Trevor Howard and Anthony Hopkins have both played Captain Bligh in significant film adaptations in 1962 and 1984, respectively. They were both in The Dawning in 1988, worth noting if for no other reason than it being Howard’s last film before his death and was dedicated to him.
For the heck of mentioning it, Howard was also in Superman (1978) with scenes opposite Marlon Brando who’d played Fletcher Christian in Howard’s Mutiny on the Bounty movie. In both movies, he viewed Brando’s character as sowing insurrection.