City Lights (1931)
10

#4 on IMDb Top 250
With the aid of a wealthy erratic tippler, a dewy-eyed tramp who has fallen in love
with a sightless flower girl accumulates money to be able to help her medically.
Director: Charles Chaplin
Writer: Charles Chaplin
Stars: Charles Chaplin, Virginia Cherrill, Florence Lee
Studio: United Artists
Genre: Romance
The silent film behind which all other silent films stand. The granddaddy of them all. In my opinion The greatest silent film of all time. A narrative and comedy masterpiece. Chaplin takes what he has learned from his craft so far and refines it into a perfect picture that showcases the best silent films have to offer.
City Lights was Chaplin's greatest box office and critical success. Despite being released well into the period where silent films were becoming outdated, Chaplin was still able to tell a story as engaging and heartfelt as anything else coming out at the time that had sound. The incredible choreography of the boxing scene, the spectacular nights on the town between Chaplin and his drunken millionaire buddy, and the relationship with the flower girl are all timeless segments that could have each been their own individual film they're so good. The romance between Chaplin and the flower girl is so convincing you'd never have known they hated eachother behind the scene. So much so that Chaplin fired and re-hired her halfway through shooting.
If there is any single silent picture to watch, this would be the one. Or maybe Sherlock Jr. Either way you can't get any better than this.