1917: The Immigrant

In 1914, Chaplin made 36 films for Keystone. In 1915, he made 13 for Essanay. In 1916 he made 9 - one for Essanay and the rest for Mutual - and in 1917 he only made 4, all for Mutual. He was quite rapidly acquiring more control, more time, and more money to make his films.
I wasn't planning to cover the most obvious films from each year, and "The Immigrant" is possibly Chaplin's most iconic short, if not the most famous short comedy of the whole silent era, but never mind.
The story has already become a regular one of Chaplin's: Tramp meets girl, tramp sees off ruffians, tramp and girl live happily ever after. This one's a bit different in that it's a film of two halves - in the first half, Chaplin is on a ship bringing immigrants to America. Here he meets - once again - Edna Purviance. Events throw them together but they say goodbye as they leave the ship to be processed through immigration.
Later, Charlie is penniless and hungry but finds a coin and goes into a cafe, where he meets Edna again by chance. After some comedy business about losing the money and dodging Eric Campbell's scary waiter, they are rescued by a rich artist who wants to paint their portrait. In the final scene the pair are in the rain outside a registry office. Charlie wants Edna to come in with him but she's shy and embarrassed. Finally he picks her up and carries her through the door. It's very sweet but I hope she didn't want a bit a bit more time to think about it.
Kevin Brownlow and David Gill's series "Unknown Chaplin" from 1983 reveals a lot about Chaplin's working methods. The standard method of making films was probably already well established - you write the script, THEN you shoot the film. It seems that Chaplin just needed the germ of an idea before getting his sets built and setting up the camera. He'd start filming, improvise, stop, refine it, film it again, and so on, then decide what happens next and start the process again from there. This accounts for the unstructured narrative of a lot of his films. It also means he shot an awful lot of film - much of the discarded material ended up in the hands of collectors, and a tiny fraction of that - clips of abandoned sequences and alternative versions with different cast members - found its way into "Unknown Chaplin". The whole sequence on board ship seems to have been a late addition to an idea that was initially just about a tramp meeting a girl in a cafe. He shot more footage for this two-reel short than D W Griffith did for his three-hour epic "Intolerance". It pays off though as the film is polished to perfection, with more detail that you're likely to pick up on one viewing. Hardly a frame is wasted. For instance, after Charlie has spent ten minutes worrying about how to pay his bill after losing his money, the artist comes over to talk to them. He offers to pay but Charlie graciously refuses once too often and is lumbered again. While the artist is talking to Charlie and Edna, he pays his own bill. The waiter takes it and returns the change - one large coin. The artist, still in conversation, dismisses it with a wave of the hand, meaning the waiter to keep it as a tip, but the waiter misses this, and returns a moment later with Charlie's bill. Still talking to the artist, Charlie steals a glance at the camera and nonchalantly pays his bill with the artist's change, tipping the waiter with the tiny coin that is his own change.
When the three leave, the waiter fawns over the artist, obviously expecting a huge tip, but receives none and glares angrily at the departing artist, who of course thinks he has already tipped him handsomely. We wonder for a moment what sort of service he'll get on his next visit.
All this action is very low-key and easily missed if you're not giving the film your full attention - which is why, since you'd be hard pressed to find them in a cinema, I'd encourage you to watch these films on blu-ray or DVD on your big HD TV, rather than on a tiny YouTube window.