Henry Graham (Walter Matthau) lives for only one thing: being rich. He doesn't have friends, hobbies, or a job. He is rich and that is all he's ever wanted to be. So it comes as a terrible blow to him to find out that all his inheritance is gone and he is staring down the barrel of poverty*. His last ditch effort to ask his uncle (James Coco) for a small loan of $50,000 comes at a steep cost. Henry must find a rich heiress and have her pay off the debt within six weeks or forfeit all his worldly possessions. Henry reluctantly hits the marriage market and strikes pay dirt in Henrietta Lowell (Elaine May), a spectacularly wealthy but clueless woman only interested in botany. Now with relief on the horizon shadowed only by the thought of being chained to this woman until death do them part, Henry sets a new goal. After all, the bargain only specified that he marry, not that she survive.
*rich people poverty, not real poverty
This is a very funny dark comedy. I wasn't familiar with Elaine May as a writer, actress, or director. Apparently, she wrote The Birdcage. Wild. A New Leaf was her directorial debut as well as her first feature-length screenplay, and she starred in it. It's incredibly ambitious and not all of it works, but enough does. Matthau has always been a wonderful curmudgeon, and this gives him a chance to shine. There are a lot of "that guy" actors in this. The one that stood out for me was Doris Roberts but you might have a different favorite.
You can only find it on the Internet Archive but it's worth tracking down.
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