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.
The English cabaret performer Ursula Martinez's most famous stage routine, Hanky Panky, is kind of Refuge in Audacity: The Comedy/Magic/Striptease Routine. Martinez walks confidently onstage in a business suit and smiles at the audience. She takes a red handkerchief from her jacket pocket, pokes it into her fist, and then makes it disappear. Then she produces the handkerchief from inside her jacket. She takes the jacket off, revealing that underneath she's wearing a bra, but no shirt; whoops up the crowd a bit, and pokes the handkerchief into her fist again: handkerchief then disappears, only for her to pull it from inside the waistband of her skirt. She then takes the skirt off, revealing her black thong, and shows off her (very nice and extremely tall) body a bit to the audience, then makes the handkerchief disappear again, only to produce it from inside her bra. She then takes her bra off, makes the handkerchief disappear again, and produces it from inside the front of her thong. Finally, she takes the thong off — leaving herself naked except for high-heeled shoes — makes the handkerchief disappear again, and finally pulls it out of her vagina and accepts the applause of a grateful audience.
The Book of Mormon has Mormon Missionary Elder Price run right into a vicious Ugandan warlord's camp in an attempt to convert him to Mormonism. His blind courageous/stupidity is so unexpected and confusing, that the soldiers, so perplexed by this, don't shoot him to death, even when he awkwardly grabs the general in order to get him to join in the choreography of the song he's singing. Though that still doesn't stop them from shoving the Book of Mormon up his rectum.