Modern Times (1936)
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At one point, there is a short shot of the text that the woman writes onto his cufflinks. If the film is stopped at that precise second, these lines can be read:
"A pretty girl and a gay old man flirted on the boulevard. He was a fat old thing but his diamond ring caught her eyes..."
The last line presumably is unfinished before the shot cuts away, but there's enough there to grasp the fundamental premise. So it basically tells that age-old tale of the not so attractive male pursuing a pretty woman, who then only reciprocates his advantages upon discovering signs of his wealth. The humour arguably comes more from the delivery than anything else. Edit