The Curse of the Jade Scorpion (2001)

  What a horrible movie.  I'm not a big Woody Allen fan anyway but this was just gross.

C.W. Briggs (Woody Allen, aged 66 at filming) is a hotshot investigator at North Coast Insurance Company, known for recovering the unrecoverable and being an inveterate skirt-chaser.  His office nemesis is Betty-Anne Fitzgerald (Helen Hunt, 38), an efficiency expert brought in to bring North Coast up the the modern standards of 1940.  At a retirement party for a co-worker (Wallace Shawn), a hypnotist (David Ogden Stiers) puts Briggs and Fitzgerald into a trance and convinces them they are in love with each other.  Unbeknownst to the audience, the hypnotist is planning to use Briggs' and Fitzgerald's positions at the insurance company in order to rob wealthy families of their jewels.  Briggs is eventually suspected after the daughter of one of the elite (Charlize Theron, 26) angrily turns him in to the police after he refused to sleep with her because he was hypnotically tranced into going out on a second robbery.  On the lam, Briggs goes to Fitzgerald's and unknowingly witnesses her also under hypnosis.  Confused by her sudden affectionate turn, Briggs confides in his retired co-worker, who recalls the hypnotist's gag.

I'm not here to bemoan the constant age gap between male and female leads that is ubiquitous in Hollywood, even though I think it's ridiculous that audiences are supposed to believe a geriatric man is the love interest of a collegiate girl unless that is a specific plot point.  I am going to discuss how blatant and disgusting it is that a 66-year-old man specifically wrote and directed a movie casting himself as the love interest of not one, but three drastically younger women.  I left out Elizabeth Berkley (then either 27 or 29, depending on which birth year is real) as the wide-eyed object of office lust because she doesn't actually figure into the plot at all.  She's literally only in the movie to fawn over a man twice her age.

Honestly, it just makes the movie unnecessarily weird.  He could have cast literally anyone else as Briggs and it would have made for a better film.  I get that Woody Allen has never shied away from making himself the butt of a joke, and casting himself as a resoundingly macho chick magnet is supposed to be funny.  It is not.  Especially not when you Google anything about him as a person.