Neil Bahadur’s review published on Letterboxd:
In many ways, perhaps the sweetest film ever made. But The Kid still, like all of Chaplin's films, is a very sad one. There's still barely enough to eat, authorities still antagonize only the proletarian classes, the "proper care and attention" of an orphanage only causes social disruption. Even as charming as the window breaking sequence is, the Tramp and the Kid have to resort to illegal work in order to make enough money to afford to eat. The Welfare Officer refuses to even speak to the Tramp, and speaks to him through a surrogate, in the Tramp's own home.
The ending is a deus-ex machina; the Tramp's look of bewilderment towards the camera as he's put incredulously into a chaffeur's car to be taken to the Woman's house tells us so. What heartbreak the movie would be had The Kid ended without it. The Tramp wanders off into the night alone and returns to his house, boarded up and the locks changed, while the Kid is separated from the person who has cared for and loved him for five years to be reunited with his biological mother via the authorities. This happens not because of biology, but because she comes from a higher social class. So the Tramp sits at his door, falls asleep, and dreams of a better place. In fact much of Chaplin deals with the inability to reconcile fantasy with reality. But even his dream is despair; reality sets in once again: the Tramp is shot and killed by a police officer. So the only hope left here is to die within his own dream.
Yet, there are moments so beautiful in this film it makes me want to cry. Almost every moment where the Tramp and the Kid are together are infused with such a joy and a profound humility that, in their comic invention, almost overpowers it's purpose as comedy. Moments like the chase on the rooftops have strange comic interludes, but as Chaplin swings one last time to hit the police officer, even after he has already hit him, I can't help but be moved. The comic becomes the heroic, silliness becomes sublimity. This is in part, I think, because of the design of the home sequences. Everything in the Tramp and the Kid's home is a kind of toy, something to be altered for more practical (and amusing) use. There is no despair in this home. The Tramp and the Kid use comic invention as a tool to rebuke and revolt against their own economic disparity. This is a movie that means a lot to me.