It wasn't really my intention to turn this blog into the Michael Caine show--we've reviewed many of his films--- but his cinematic entanglements with Jude Law really are worth viewing.
Try 1966 classic Alfie in which Michael Caine plays what used to be referred to as a playboy who breaks hearts right and left around swinging London. His inability to commit to anything catches up to him, with heartbreaking results. Caine's monologues and asides make the movie.
It turns out that Jude Law is a dead ringer for a young Michael Caine, see the 2004 remake of Alfie if you don't believe me.
Second, watch the chilling yet humorously absurd adaptation of Anthony Shaffer's play, Sleuth, with Jude Law as the young lover confronting the wealthy husband played by Caine, at his country estate. Cat and mouse game ensues. This dvd is a great choice for theatre lovers. Harold Pinter wrote the screenplay, and Kenneth Branagh directed. In the original 1972 film (not yet at CPL) Caine plays the young lover with Laurence Olivier in the cuckold's role.
If you can't forgive real life Jude Law for alleged Alfie-like behaviour, check out Factory Girl with Sienna Miller playing Warhol circle socialite Edie Sedgewick.