Always the groomsman, never the groom.

The actor who has gone zero for four in the lead acting category, but two for two in supporting actor wins is Michael Caine. The first of Caine's wins was at the 1987 Oscars for his turn in Hannah and Her Sisters. The film also won for Best Supporting Actress (Dianne Wiest) and Best Screenplay (Woody Allen), and it was nominated for Best Picture and Best Director (Woody Allen).

The film tells the intermingling stories of the titular siblings and their large cast of relatives, husbands, ex-husbands, business partners, etc. Hannah (Mia Farrow) is the one successful person among the group, and her success and generosity provide support for everybody around her, support that they resent her for despite their inability to get by without it. Hannah's husband (Caine) spends the first half of the film trying to star an affair with her sister Lee (Barbara Hershey), then spends the remainder of it trying to end the affair. Her other sister, Holly (Wiest), is constantly mooching money from her to start side-jobs in order to support herself (and pay off debts, and support an on-again-off-again cocaine habit) while waiting for her acting career to take off. Meanwhile, Hannah's ex-husband (Allen) has a health scare that forces him to face his own mortality, and she must hold together the tumultuous relationship between her parents (Maureen O'Sullivan and Lloyd Nolan), a not-quite-famous showbiz couple.

Hindsight has not been kind to this film. It is well-made, well-written, and well-acted, but in the end, I felt that it was very been-there-done-that. Which is not exactly fair to this film. Wiest, better know to most as the mother in Edward Scissorhands, builds a very believable character, flaky, needy, and falsely "unique," but not to the point of being entirely unlikable. Caine does a wonderful job in his role, in which he essentially plays the role of Woody Allen - a novel and interesting choice at the time that has since become such a staple of Allen's later films that the novelty has completely worn off in retrospect. The screenplay is complex and involving, seamlessly weaving together several interesting stories in such a way that each story makes the others feel fuller, richer, and more fleshed-out. But, at the same time, the action all feels very much like a stereotypical Woody Allen film - a bunch of neurotic, over-intellectual New York City dwellers, none of whom have to actually work for a living, spend all of their time screwing up all of their relationships and whining about their own insecurities. It is different enough from Annie Hall and Manhattan that, at the time, the film was still fresh. But when he followed it up with Crimes and Misdemeanors, Husbands and Wives, Deconstructing Harry, Celebrity, and so on, the films have all started to sort of blend together to the detriment of the entire catalog.

Movie trivia question: Part 2 of the question that this review started to answer. What was the other film for which Michael Caine won the Best Supporting Actor Oscar?