Around 1912, Groucho Marx saw Charlie Chaplin for the first time in Winnipeg (Canada), then an important city on the Vaudeville circuit. Groucho happened to be passing by the Empress Theatre where Chaplin was playing and hearing roars of laughter he decided to go in. In his autobiography Groucho and Me (1959), Groucho recalled telling his brothers about seeing Chaplin for the first time: "I told them I had just seen a great comic. I described him . . . a slight man with a tiny moustache, a cane, a derby and a large pair of shoes. I then penguin-walked around the depot, imitating him as best I could. By the time I finished raving about his antics my brothers could hardly wait to see him."
Doing a vaudeville tour themselves, Groucho and his brothers caught up with Chaplin in Vancouver a month later and met him backstage. In his autobiography, Groucho said that they became "real chummy" with Chaplin in the weeks that followed and even went to a "sporting house" together (according to Groucho, Chaplin was "terribly shy" back then). It wasn't until years later that Groucho ran into Chaplin again in Los Angeles, but by then Chaplin was already a star having become the world's most famous comedian.
Groucho greatly admired Chaplin. While he was not in the habit of complimenting other comedians, Groucho said about Chaplin in the May 1936 issue of Motion Picture magazine: "I know now there will never be anyone like him. He's in a class by himself, just as he has always been", and again in his 1959 autobiography: "He's still the greatest comic figure that the movies, or any other medium, ever spawned". Chaplin also admired Groucho, wishing he could talk on screen like Groucho did.
During the 65 years of their acquaintanceship, Groucho and Chaplin saw each other perhaps a dozen or so times (according to Hector Arce, author of Groucho (1979)). One of the occasions where they had met was at dinner at the famous Chasen's restaurant in Hollywood on 4 September 1940. Groucho wrote a letter to his good friend Arthur Sheekman the next day, talking about his conversation with Chaplin. An excerpt from the letter is seen below (only the part that deals with Chaplin) with interesting remarks from Groucho such as "He's very odd. In some ways, he has no sense of humor at all [..]". Also, Groucho mentioned in his letter what I already mentioned above, i.e. that Chaplin envied him for talking so "swiftly" on the screen. Groucho later said it was the greatest compliment anyone had ever given him.
September 5, 1940Dear Sheek,I'm working terribly hard and I don't like it. I really don't mind the work; it's just that when I work, I sleep badly; and it's insomnia rather than labor that makes me feel lousy.Last night I had dinner with Chaplin at Dave Chasen's and he was in high humor- unusual for him. He told me, among other things, that he's not Jewish but wishes he were. He said he was part Scotch, English and Gypsy, but I think that he isn't quite sure what he is. He's very happy about his movie [The Great Dictator]. He ran it yesterday for the Breen Office - it runs over 13,000 feet and there wasn't a foot cut out of it. He thinks it will be a big hit. He's very odd. In some ways, he has no sense of humor at all and then again it's wonderful. He told me he hated the English but that he hoped they would win the war. He also hates Noel Coward and even refuses to see his playlets, which are now running at El Capitan.At the finish of the meal, the most astonishing thing happened: he grabbed the check (for six; it came around $30*) and refused to let me have it. I was quite relieved, but luckily I'm sunburned and I don't think the white or my nervousness was discernible through the tan. He has a reputation for stinginess but I have always found him generous- not only with his money but with his praise. He thinks I'm wonderful and said that he envies my glibness and wishes he could talk as swiftly on the screen as I do. Well, enough of Chaplin and me![....]
[*According to the inflation calculator $30 in 1940 would now be $541.90]
Source: The Groucho Letters: Letters from and to Groucho Marx (1967)