Alfie

Alfie. 1966 Paramount Pictures.
Starring: Michael Caine, Shelley Winters, Millicent Martin, Julia Foster, Jane Asher, Alfie Bass
Director: Lewis Gilbert
Buy Alfie (1966) from Amazon.

Yes, this one was remade in 2004 starring Jude Law and Marisa Tomei.

The original, however, stars Michael Caine as Alfie Elkins, a promiscuous young man who seems to be shagging most of the female population of London when he isn't breaking the fourth wall trying to justify his actions. Usually, what Alfie tells the audience is the opposite of what we see him doing onscreen. Alfie is seeing Siddie (Martin) for little more than romps in parked cars, while his live-in bird Gilda (Foster) waits at home

Alfie's life begins to change when he ends his relationship with Siddie, and subsequently gets Gilda pregnant. Fatherhood seems to mellow Alfie out a little bit, but his reluctance to commit to Gilda drives her to marry a bus driver (Graham Stark). Alfie is then diagnosed with "shadows on the lungs", which means that he won't be able to go near his son. Checking into a convalescent home, Alfie meets another patient named Harry (Bass), whose wife he gets pregnant in a one-night stand. Harry's wife chooses to terminate the pregnancy, which devastates Alfie.

Having met an older, American woman named Ruby (Winters) while taking holiday pictures, Alfie decides to abandon his carefree ways, and settle down. Alfie chooses Ruby, but the day he finally tries to tell her, he finds Ruby in bed with a younger man.

Alfie was based on Bill Naughton's novel and play of the same name, and it earned several Academy Award nominations, including Best Actor for Michael Caine. Recommended movie!