The Adventurer (1917)/The Pilgrim (1923)
(I only posted a link to the Adventurer because I couldn't find a good full copy of The Pilgrim streaming)
I decided to watch the Adventurer as a lark (because it was the only other Chaplin film on a silent film list I hadn't seen yet), but it turns out to be quite appropriate. Both are "fish out of water" comedies, and both begin with the Tramp as an escaped convict taking on a new identity. In the Adventurer, he claims he is a Commodore, and in The Pilgrim it is assumed that he is a minister.
The basic joke of both is that the Tramp must act like an educated, cultured gentleman, when he is anything but. In The Adventurer, this is shown by Chaplin eating ice cream without a spoon, realizing his mistake, which then causes even more mayhem. In The Pilgrim, it is primarily shown by him being told he must lead a worship service, when it is clear he had never been to one in his life. The last is a hilarious sequence.
The real difference is what Chaplin learned about comedy in the intervening years. Although he was a matured comic in his final Mutual film, and the timing and story of his comedy is coherent and well ordered. But in The Pilgrim we can see that he also learned about the necessity for real drama to make the human connection with those in the film. It isn't enough to add some tension, he pursued melodrama and truly heroic action.
A comparison of the endings of each film also shows quite a bit of maturity. This is surprising, really. Many directors and writers and comedians have a schtick and stick with it, not growing. Chaplin has his bag of tricks, but he is constantly expanding and improving his art. It is this that makes him an artist and not just a comedian.
The Adventurer-- 3.5/5
The Pilgrim-- 4/5