Charles Chaplin was a genius, a master, a remarkable actor, an outstanding director and a legendary person. I watched all of his movies and read his autobiography and there's no need to say how much I admire this man - he will always be my number one actor and director of all times. Period.
Charlie started out his career very early and by the age of twelve already had an experience many grown-ups would be jealous of. So when the opportunity arose for him to make it big he took it and came to America in the early 1910s when the silent cinema was already blossoming. Charlie signed a contract with Mack Sennett's Keystone who produced farce and slapstick comedies and the rest is history; many of his early movies I dislike on the basis of them being just too silly, one-dimensional, at times unfunny and lacking that real "Chaplin" feel that he got famous for later. Everyone should start someplace and any place is a good start as long as you've got patience and enough talent to carry on.
The earliest of his movies that I consider a masterpiece is "The face on the barroom floor" (1914). Charlie had already a couple of dozen movies under his belt before this one came along; it still was a farce comedy but what differed this one from the rest was the presence of the soul in it. The movie was based on the poem of the same name and told a story of a broken-down person who fell in love but was left for somebody else. The intertitles in the movie are experts from the poem and Charlie brings it to life masterfully with his performance balancing between slapstick and drama the way only he could do it - brilliantly. "The face on the barroom floor" is only 11 minutes long but it showed all of Charlie's potential and talent to the world and has become his first of many successes in the world in cinema.