Director: Paul Thomas Anderson
Year Released: 2002
While I'm not comparing the two in terms of comedic talent, you could probably say that both Chaplin and Adam Sandler are a little alike in that they are pretty much the same 'character' in all of their films. Chaplin was the 'Little Tramp' whereas Sandler always plays the same goofy faux-teenager, a kid in an adult's body, his chubby face hiding seething rage. Anderson realized this, and put this Sandler 'character' in a romantic-comedy that has dark undercurrents, and really plays with the idea of Sandler as a passive-aggressive who never completely developed emotionally, stunted as 'a man' because of his sisters' abusive bullying. The result is a highly quirky experiment, one that doesn't always work but is consistently amusing and startling (it falls apart at the end with the Philip Seymour Hoffman subplot/shouting match) and reminiscent of stuff like Rene Clair's Le Million: the lottery ticket is actually frequent flyer mileage from pudding coupons. The cinematography and lighting are glorious, and the heavy usage of flaring white light (amid an unusually florid color scheme) could represent the hero's emotional redemption. It's surprising and one-of-a-kind, and destined to draw a cult audience. It's Adam Sandler's The Cable Guy.