Harry Block is a writer who loosely veils his own sexual foibles and family life in his novels. He's about to be honoured by his alma mater in upstate New York, even though he was kicked out as a student, but he can't find anyone to go with him; so he takes a black prostitute called Cookie. Then his friend, Harvey, with a heart complaint, joins him before he kidnaps his son, Hilly, from his school chaperone.
Meanwhile, his ex-wife (one of three), ex-therapist (one of six), Joan (Kirstie Alley), is irate with him and keeps interrupting a session with one of her patients to shout at Harry for being such an unapologetic lover of whores and a terrible influence on their son. Oh, and this: "So now you're blaming me because I don't go out with you enough, to meet strangers to FUCK!" (He had been sleeping with one of her patients.)
The movie has a fast-paced feel with jump-cuts like Jean-Luc Godard's Breathless (1960). Intercut are scenes from Harry's fiction, such as when the Harry character is caught fucking his sister-in-law by their blind grandmother while the rest of the family are outside having a barbecue; or the short story about Mel, an actor (played by Robin Williams), who goes out of focus on a movie set and has to make his family wear thick, black-rimmed glasses to see him in focus.
There is a great cast including Billy Crystal as Harry's writer friend who marries Fay (Elisabeth Shue), a young admirer of Harry's whom he tells not to fall in love with him before falling for her himself. Crystal also plays the Devil, who has some brilliant lines:
Harry: What? You have air-conditioning in Hell?
The Devil: Sure! Fucks up the ozone layer!
The Devil: You ever fuck a blind girl?
Harry: No. That I never did.
The Devil: Oh, they're so grateful.
Plus Demi Moore, Mariel Hemingway (from Manhattan (1979); Ernest Hemingway's granddaughter), Tobey Maguire and Bob Balaban (a regular in Christopher Guest's movies).
Nugget: written, directed by and starring Woody Allen - as if you hadn't guessed by now.