1921. dir Charlie Chaplin, starring Charlie Chaplin, Jackie Coogan.
Seen it before? No.
That little mustache is a great look; too bad that Hitler guy had to ruin it.
This is the earliest movie on the list - and also the shortest at only 50 minutes. (I think there's a 68 minute cut out there, but it's not on the DVD.) It's one of the first movies to mix comedy and drama. The drama aspect is a little overwrought and melodramatic but Chaplin's brilliant physical comedy balances it out nicely.
Charlie Chaplin wrote, directed, starred, produced, and wrote the music. He also invented the Snuggie. (no, seriously! watch the movie and you'll see what I mean.)
Chaplin plays his famous "tramp" character with the flat-footed duck walk and the ridiculously over-sized clothing. Jackie Coogan - yes, the same one who played Uncle Fester much later in life - plays a little orphan boy whom The Tramp adopts. The kid is pretty useful; he beats up a much bigger kid, makes a whole stack of pancakes, and helps The Tramp with his moneymaking scam. I should show Daniel this movie...
Position on the list: 192
Not to be confused with: Disney's The Kid, which came out in 2000, stars Bruce Willis and Spencer Breslin, and is fucking terrible