ChalesGrodin goes overboard for Cybill Shepherd in
The Heartbreak Kid
Matthau ponders whether or not to toss May overboard
at the end of A New Leaf
Elaine May is also the writer/director/star of A New Leaf. Walter Matthau plays Henry, a spoiled rich middle-aged man who discovers he is about to run out of money. Having no marketable skills, he seeks out a rich wife to support him. Just when all hope seems lost, he comes across Henrietta (May), a rich botanist with no family left and a big inherited bank account. Henrietta is clumsy, but falls for Henry. The character of Henry is a bit of a louse, but I find it difficult to dislike Matthau here. I also find May charming, even when she's dropping plates or spilling food on herself. I liked this film a bit more than The Heartbreak Kid, so if I were going to recommend one May film, it would probably be A New Leaf.
Dustin Hoffman and Warren Beatty in
Elaine May's Ishtar
May later directed Ishtar in 1986, which was known for being one of the biggest bombs of the era at the time. I actually rather liked it and it seems to be going through a bit of a reappraisal.
Fans of May may want to check out the book Improv Nation by Sam Wasson. The book talks about the early days of the art of Improv and May (along with her partner Mike Nichols) was undoubtedly one of the chief pioneers of the form.