How about Leonardo diCaprio to Kate Winslet?
[spoiler]Leonardo diCaprio played Romeo in Romeo + Juliet, which character was also played by Leslie Howard in *Romeo and Juliet * (1936).
Leslie Howard played The Scarlet Pimpernel/Sir Percy Blakeney in The Scarlet Pimpernel (1934), which character was also played by **Anthony Andrews ** in The Scarlet Pimpernel (1982).
**Anthony Andrews ** played Professor Moriarty in Hands of a Murderer, which character was also played by Jared Harris in Sherlock Holmes: A Game of Shadows.
Jared Harris played King Henry VIII in The Other Boleyn Girl (2003), which character was also played by Jonathan Rhys Meyers in The Tudors (2007-2010 TV series).
Jonathan Rhys Meyers played Dracula in Dracula (2013- TV series), which character was also played by Christopher Lee in Horror of Dracula.
Christopher Lee played Sherlock Holmes in Sherlock Holmes and the Deadly Necklace, which character was also played by Peter Cook in The Hound of the Baskervilles (1978 TV movie, and admittedly also described as a farcical remake).
Peter Cook played The Devil in Bedazzled (1967), which character was also played by Elizabeth Hurley in Bedazzled (2000).
Elizabeth Hurley played Delilah (“Dalila”) in Samson and Delilah (1996), which character was also played by Hedy Lamarr in Samson and Delilah (1949).
Hedy Lamarr played Joan of Arc in The Story of Mankind, which character was also played by Geneviève Bujold in Saint Joan (1967 TV movie).
Geneviève Bujold played Cleopatra in Caesar and Cleopatra (1976 TV movie), which character was also played by Elizabeth Taylor in Cleopatra (1963).
Elizabeth Taylor played Maggie Pollitt in Cat on a Hot Tin Roof (1958), which character was also played by Jessica Lange in Cat on a Hot Tin Roof (1984).
Jessica Lange played Blanche DuBois in A Streetcar Named Desire (1995), which character was also played by Vivien Leigh in A Streetcar Named Desire (1951).
Vivien Leigh played Emma, Lady Hamilton in That Hamilton Woman, which character was also played by Glenda Jackson in The Nelson Affair.
Glenda Jackson played Queen Elizabeth I in Mary Queen of Scots, which character was also played by Jean Simmons in Young Bess.
Jean Simmons played Miss Havisham in *Great Expectations * (1989), which character was also played by Charlotte Rampling in *Great Expectations * (1999).
Charlotte Rampling played Anne Boleyn in *Henry VIII and His Six Wives *, which character was also played by Helena Bonham Carter in Henry VIII (2003).
Helena Bonham Carter played Ophelia in Hamlet (1990), which character was also played by Kate Winslet in Hamlet (1996).
(Needless to say, I didn’t come up with this off the top of my head; I cheated and followed links through IMDB.)[/spoiler]