I'm a lifelong fan of Charlie Chaplin, and Modern Times is one of his funniest and socially relevant films. Fun fact, it's the film that got him blacklisted as a communist by the HUAC, due to its anti-capitalist leanings and celebration of individual freedom. There's definitely some truth to that, but I'd argue the film's comedy outweighs its social intentions. This was also the last time we would see the Tramp, though Chaplin's character in The Great Dictator does come close to resembling the character. Not Hynkel, of course. The other one.
Modern Times sees the Tramp as a factory worker turning gears all day, every day. He has a hilarious run-in with an automatic food dispenser that is easily one of Chaplin's funniest scenes in his entire catalog. The Tramp has a nervous breakdown and is arrested for inciting a riot, then is released when he helps stop a prison break by accident. Outside again, he encounters a beautiful vagrant (Goddard), and the two fall for each other immediately. Chaplin and Goddard have great chemistry and sell a believable relationship. One of the film's standout scenes involves the Tramp on roller skates in a department store, not realizing he's skating near a very high ledge. Chaplin's skills at physical comedy were always unmatched and still hold up.
Modern Times ends with the Tramp's only talkie scene, where he sings a gibberish song to a crowd of diners. It's absolutely hilarious and a great send-off to Chaplin's iconic, timeless character. Despite his personal demons and perfectionist streak, Chaplin's films remain some of the best comedies of all time. Modern Times ranks among his funniest.