It's 1930's London. Jim Crocker (Sam Rockwell) is the infamous Piccadilly Jim, a hard-partying playboy with a reputation for womanizing and fighting. His father Bingley Crocker (Tom Wilkinson) is a nice guy who only wants the best for him. His stepmother Eugenia Crocker (Allison Janney) is obsessed with social climbing the class system and win against her sister Nesta Pett (Brenda Blethyn). Jim falls utterly for Ann Chester (Frances O'Connor), but she utterly hates Piccadilly Jim although she has no idea what he looks like. He had written a bad review of her poems and ended her career. He assumes the false identity of Algernon Bayliss, a prim and proper Englishman, in order to pursue her.
To be fair, this movie is trying to be an outside-the-box comedy with a lot of eccentric touches. First, it's hard to buy Tom Wilkinson as the father of Sam Rockwell. Wilkinson is being his British self and Rockwell is going full out wild American. I'm sure that there are ways to explain the difference away. It just feels weird. The same goes for Allison Janney and Brenda Blethyn unless they grew up on the opposite sides of the Atlantic. Finally, I initially thought that Ann Chester is being played by Naomi Watts. I like Frances O'Connor, but she is ill-fitting in this role and I couldn't erase Naomi Watts from my mind.
I like some of this, but every other thing feels off. I'm never sure which part feels more wrong. It could be the differing tones. It could be the unrealism. It could be the unexpected turns. It's probably the odd casting. It could be all of them and more.