[mousepod]

Great post, Boingonut! I really dig Chaplin, but I got into his work "backwards". Like everyone in my generation (i.e. born in the '60s), I was originally exposed to his work through clips on "comedy cavalcade"-type shows on TV and silent shorts - there wasn't really much of an opportunity to see full-length silent movies when I was an adolescent. I knew who Chaplin was, as I knew who Harold Lloyd and Buster Keaton were and though I understood that they were geniuses and innovators, I preferred Laurel & Hardy and Abbott and Costello.
Then, when I was a college freshman, I was exposed to the film 'Monsieur Verdoux'. Holy crap. I knew about mainstream black comedies (like Arsenic and Old Lace), but this one had bite. I was stunned. I decided to give Chaplin another chance, and I was glad that I did. Clearly, some of his work need context to be fully appreciated. I might even suggest checking the out the biopic starring Robert Downey, Jr - hell, it was directed by the guy who made 'Gandhi'.
Anyway, I know I'm being long-winded here, but I guess my point is that there's nothing wrong with introducing Chaplin into your world through his later talkies and working backward to his "classic" silents. Understanding who he was and what he was trying to say with his work will make you appreciate his films even more.
Oh, and Keaton is fantastic, too. And I'll even throw in a plug for the much underappreciated Wheeler and Woolsey.