Ah, Chaplin! Well, for a fascinating look into the man and how he created his timeless character of the tramp (swanky before swank was coined), you might want to seek out the excellent Kevin Brownlow documentary, the Unknown Chaplin. His films were not born out of genius, they evolved, slowly and painfully while he waited and worked through gags to find the one that fit.
Of the acknowledged 3 great silent comedians, I also prefer Keaton, who is truly timeless (his affinity for cocktails, though damaging to him personally and professionally when he lost control, he was a mighty man with a shaker). Keaton's films play as well today for modern audiences, probably better than they did in the 1920s because they are not nealry as sentimental and they are constructed masterfully. Steamboat Bill Jr. and The General are but two examples.
Harold Lloyd to me is also preferable to Chaplin, at least in the full length films. Once he found his character, seeing him in the theater is a great experience. Safety Last is a classic, as are Dr. Jack and The Freshman, nice touches all the way around.
Chaplin comes in third for me, but this is not a dig. I simply prefer him when he was a little more raw, a naughty character, not above tweaking authority (Mutuals and Essanay's - he is especially charming with his leading lady Edna Purviance). I cannot watch The Gold Rush nor City Lights any longer (in particular, after seeing the above-reference Unknown Chaplin). Too much sentiment and bathos for my taste. Again, Keaton preferred, less sentimental. Maybe I just don't have that slapstick comedy gene so needed to appreciate some of his stuff, I feel there is so much that is self-conscious. That said, I do LOVE the wicked sense of humor in Monsieur Verdoux - much in the vein of Ealing's Kind Hearts and Coronets - not to be missed, but I digress.
Chaplin is important, no question, pioneer, absolutely! Worth watching today, yes. For cool, give me Buster anyday!
Snow