Our Favorites & How to Watch Them:
A New Leaf (1971): The blackest of black comedies. Walter Matthau is a playboy who burns through his family’s inheritance and loses his damn mind trying to maintain a certain lifestyle. Instead of killing himself -- which he briefly considers -- he decides to try to marry into money. He meets Elaine May, who plays that classic combination of botany professor/heiress, and considers murdering her, but -- oops -- starts to fall for her instead.
Mikey and Nicky (1976): Peter Falk and John Cassavetes play a couple of friends trying to escape a hitman/the mob/general bad stuff but find the real problem they should be confronting is their own friendship.
Ishtar (1987): A couple of terrible songwriters (Warren Beatty and Dustin Hoffman) can’t get work in the U.S. and decide to head to Morocco to become lounge singers, as one does. They then get mixed up in a plot to overthrow the Emir of (fake nearby country) Ishtar… as one does.
Dear Elaine May,
Not to start this on a bitter note, but the fact that your directing career has been so unfairly truncated is one of the bullshittiest pieces of bullshit to have ever occurred in the American film industry. Despite having directed four genuine masterpieces, you haven't made a feature in 29 years -- since Ishtar -- and that is frankly unacceptable. In the year of our lord 2017, can't we finally rewrite history on the quality of Ishtar as a film? Have we now reached enough of a critical mass on acknowledging its position as, sure, a big old flop, but a genuinely terrific big old flop? It's basically the funniest and -- as you intended -- a more than worthy successor to all the Bing Crosby and Bob Hope "Road" movies from the 1940s. One could argue that the only reason it received negative reviews in the first place was due to some critics being unable to separate behind the scenes drama from the film itself. And yes, if a man had made Ishtar, etc. etc. etc. Okay, so, with that out of the way: the good. If I could come up with my ideal movie, it would probably be one in which you direct yourself as a rich botanist involved in a romance with Walter Matthau. Luckily for me that's a movie that actually exists: your first film, A New Leaf. Then there are Mikey and Nicky -- a buddy film that subverts the sexism of buddy films -- and The Heartbreak Kid -- a romantic comedy that subverts the sexism of romantic comedies (that also happens to be ranked as one of the greatest comedies of all time on basically any list that would rank such things). And I'm not in the habit of talking about women as they relate to the men in their lives, but I would be remiss if I didn't mention your relationship with Mike Nichols. Your comedy team Nichols and May produced sketches that, as far as I'm concerned, still haven't been topped in sketch comedy. Your screenplays for Nichols's movies The Birdcage and Primary Colors are some of your best writing. And if I can't watch a new feature by you, the American Masters you directed on Nichols after his death is a pretty amazing consolation prize. So this letter doesn't pass the Bechdel Test. Sorry.