Richard from Richard III, by William Shakespeare, hits on Lady Anne, the widow to a man HE KILLED. He does this while the corpse of her father-in-law (who he also killed) is present, and his wounds are bleeding again as a warning from beyond the grave. He gets her.
Autolycus from A Winter's Tale, also Shakespeare. He does such things as pretend to have been injured and robbed, pick the pockets of people who try to help him, and then describe the robber as himself. Later, in disguise, he encounters the guy he ripped off again, and sympathizes with his concerns about thieves.
13: The Musical provides us with the musical number "All Hail The Brain/Terminal Illness," in which our protagonist Evan thinks up many a Zany Scheme of how to get himself and his friends into an R-rated film, finally convincing his mother to buy the tickets by having his terminally ill friend, Archie, asking Evan's mother to buy the tickets for them.