The Pick-up Artist (1987)
Directed by James Toback
A womanizer meets his match when he falls for the daughter of a gambling addict who is in debt to the mob.
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What critics compared The Pick-up Artist to
Master cocksman Jake (Jason Sudeikis), a fast-talker in the mold of the master cocksman played by Robert Downey Jr. in The Pick-Up Artist, peppers his speech with references to Aaron Sorkin and "Game of Thrones" and Wes Anderson and Malcolm Gladwell because he's totally hip.
Hitch (Smith), a smooth, fourth-wall breaking ladies man (like Alfie or Robert Downey Jr. in The Pick-Up Artist), makes his living helping the helpless attract the attention of their ladies fair.
He wrote and directed the underrated The Pick-Up Artist (another semi-autobiographic story, in which Robert Downey Jr. was the Toback surrogate) in 1987 and followed that up with the documentary The Big Bang.