Small Time Crooks (Woody Allen) - 2000

This is Woody's rags-to-riches-and-back-to-rags movie.  He plays a career criminal who is married to a former topless dancer (Tracey Ullman) who is his reluctant partner in crime.  Woody plans an underground bank heist with a cookie store as a front.  As you might imagine, cookie sales are wildly successful and the bank robbery is a bust.  Woody & Tracey become extremely wealthy with the cookie franchise known as "Sunset Farms."  They try to upgrade their circle of friends and become more cultured by holding parties for the upper class and attending boring plays and art shows.  Woody wears a series of bad suits and tells his low-class jokes at the parties ("Did you hear about the Polish carpool?  They meet at work.").  Elaine May is excellent as Tracey's ditsy cousin, in what may have been her last acting performance.  When Tracey goes to Europe with Hugh Grant, Elaine subs for her in Woody's latest scheme (jewelry theft).  She also reminds Woody that: "There's more to life than turkey meatballs."  Sunset Farms goes broke when the accountants take the money and run to South America.  When Hugh discovers that Tracey is broke, he dumps her and goes off to work with Renee Zellweger in Bridget Jones's Diary.  And, Woody & Tracey live happily ever after without all that money. [JAM 10/9/2010]

["I named the character May when I wrote it and Elaine was the first choice, as was Tracey.  Zero problems with Elaine.  She shows up on time, she knows her lines, she can ad-lib creatively and is willing to.  If you don't want her to, she won't.  She's a dream.  She puts herself in your hands.  She's a genius, and I don't use that word casually.  It's in her voice.  Tracey's also a massive comic talent - limitless in her ability.  Two hilarious women." Conversations With Woody Allen - January 2000]