Five Most Awkward Moments of Charlie Sheen's Detroit Show

THR critic David Rooney recounts some of the cringeworthy moves Sheen pulled during his live show Saturday.

DETROIT, MI -- The five most awkward moments in Charlie Sheen's Detroit show:

1. Telling the audience this seemed like the right city to score some crack. To say this didn't go over well is an understatement.

2. Taunting hecklers by telling them they bought tickets without knowing what they were getting. Not a good plan to tell an audience they made a bad investment.

3. Killing time by showing RPG (Rocket Propelled Grenade), a 1986 film "about redemption" that Sheen wrote and directed, with Clint Howard and a young Johnny Depp. When loud booing cut the film short, Sheen said, "OK, so RPG's a bomb. Whatever. Tonight is an experiment."

4. Boasting to a hostile crowd about his new app, called The Masheen: "Let's see, I have an app, you guys have zero." Nobody likes paying premium prices for schoolyard one-upmanship.

5. Cutting to a musical break to allow the audience to "wake up" and then not returning afterwards. When the houselights came up abruptly, the audience looked shellshocked, though the smartest thing Sheen did all night was deciding not to take a bow.