Regarding Chaplin in general: I bought the Curzon Artifical Eye blu-ray collection of Chaplin films a few months ago on a whim after watching a documentary about him and have been trying to work through them. The trouble is, I'm just not sure if Chaplin is really for me. I can't exactly put my finger on it, but there is something about him that I find a little bit off-putting. I don't find him inherently funny, I find that I have to make an effort to engage with his style of humour. I haven't seen enough of Buster Keaton to make a fair comparison, but what I have seen (Sherlock Jr, for example) I just found immediately and effortlessly funny - properly, laugh-out-loud funny. Ditto Laurel and Hardy. With Chaplin's films I smile occasionally but very rarely actually laugh.
Regarding The Kid specifically: I would say it is almost-but-not-quite a feature film. I think it runs to about 53 minutes (this is the 1971 re-release), but if you take away the superfluous dream sequence which makes up the last part of the film it would be somewhere around 45 minutes. There's nothing particularly wrong with the dream sequence in itself, and a lot of people love it apparently, I just don't think it belongs in this film. The tone of it is very different to the rest of the film and I have not been able to come up with anything other than very tenuous arguments for it having a thematic resonance with the film as a whole either. It's also slightly troubling that the sequence features a 12 year old Lita Grey made up to look older and play a 'vamp', given that Chaplin started sleeping with her when she was 15. But - I don't want to get tangled up in the separating-art-from-artists debate. After the dream sequence the film ends abruptly with a tagged on happy ending.
Like most of what I have seen of Chaplin's work, The Kid is mildly amusing in places and quite sentimental. I feel compelled in almost every review I write to restate that I am not a film expert - I know a little bit about a lot of things when it comes to cinema. People with far greater knowledge than I could explain the importance of this film in the context of cinema... all I do know is that F.W. Murnau made Nosferatu about a year after Chaplin made The Kid and that (Nosferatu) is one of my favourite films (silent or otherwise) of all time. My point being that there are other films from this era to which I respond intuitively. With Chaplin, my honest feeling is that I find them interesting in terms of film history and mildly entertaining, but ultimately not really to my taste.
The opening title of ‘A picture with a smile—and perhaps, a tear’ sums it up; an enjoyable silent movie (apart from the pointless dream sequence).