Drew Edelstein’s review published on Letterboxd:
The most remarkable thing about Chaplin is how personal his films are. Each feature he directed in some way echoes a deep aspect of his being, most often seen in the way The Tramp is portrayed. Chaplin grew up poor and never forgot it; even when he was unfathomably rich by the time of Modern Times, he still told stories through the lens of his early life, molded through financial hardship and a broken family life.
The Kid may be the most direct reflection of Chaplin's childhood. Jackie Coogan's literal abandonment echoes the tumultuous shifts in custody that Chaplin suffered, the resonance of the ending in large part due to the degree of wish fulfillment it likely served for Chaplin. The vilification of the orphanage similarly reflects Chaplin's rocky experience in the custody of the foster system, passed around from school to school as the condition of his parents grew ever worse. Even though the movie downplays how awful Chaplin's upbringing was in reality, I think the core of the film lies in how Chaplin finds fantastical resolutions to the unsolvable struggles of his youth.
Of course, Chaplin hangs a strong story on top of the abstractions of his personal tragedies. The dynamic between him and Jackie Coogan is exceptional, and the paternal affection the story demands is delivered in spades through Chaplin's performance. There's also some fantastic slapstick that ranks with the best in Chaplin's filmography; the child boxing match and the cat-and-mouse chases with the policeman have aged like fine wine. Sequences like this hold a certain sense of earnestness, easily the picture's greatest strength; it never feels like cinematic self-therapy, instead delivering on it's famous promise of telling a story with a laugh and a tear.
The film's pull for me was somewhat tainted by Chaplin's later career, sadly. Chaplin is a really problematic figure when you look at the nitty-gritty of his life story, and in particular his relationship with women reaches Bojack Horseman levels of discomfort. Here, the flirtatious angel, played by 12 year old Lita Gray, would marry and bear Chaplin's children a scarce 4 years later. Chaplin had a tendency to cast his romantic flames in his ongoing projects that is awkward in retrospect, but there's an inherent wrongness to the future between Lita Gray and Charlie that soured me to the movie to a really sorry degree. I love Chaplin's work in a bubble but I think it's hard to ignore the degree to which his relationships bled into his work; knowing how awful this specific pair would turn out makes it hard to enjoy their screen time at face value.
Luckily the core of the movie is still excellent regardless of my personal qualms, and I'd still happily recommend The Kid to anyone interested! It's definitely the most revealing and personal movie Chaplin ever made though, for all the good and evil that may bring.