James Stewart in Vertigo to Liev Schreiber in Kate and Leopold
James Stewart was in Vertigo (1958) with Kim Novak,
who was in Strangers when we Meet (1960) with Walter Matthau,
who was in Hanging Up (2000) with Meg Ryan,
who was in Kate and Leopold (2001) with Liev Schreiber.
Kathy Bates in Fried Green Tomatoes to Jane Darwell in The Grapes of Wrath.