Charlie Sheen is being roasted in a Comedy Central special airing on Sept. 19. This is also the day that Ashton Kutcher's first episode of Two and a Half Men is set to air, which I highly suspect is a deliberate move on Sheen's part to stick it to CBS. A "you take my show, I'll take your ratings" type of thing.
I'm-a be honest: I follow Sheen on Twitter. I watched the 20/20 special with him and his now-ex-goddesses, with my mouth agape. I read gossip about him out of perverse curiosity, sort of like how I read gossip about Amy Winehouse.* But I don't think this is going to be funny.
Sheen is such a mess that I suspect the jokes will just be plucking low-hanging fruit. "Charlie Sheen does a lot of drugs and has a lot of sex with a lot of porn stars. WINNING!" Remember James Franco in drag at the Oscars, talking about how he'd just gotten a text from Sheen? That was really weak. I think that's what to expect at the roast.
Seth Meyers' remarks at the White House Correspondents' Dinner worked (boy, did they work) because they were topical and specific. That bit about how he didn't think Obama was going to release his birth certificate was great, because it showed that he was paying attention. That's sharp, biting wit. Even when he talked about the obvious, like how America is broke, he did so in a way that wasn't so trite. Or when he took on Trump ... Trump is a completely ridiculous person, but he talked specifically about the ways in which he was being ridiculous in current events. (That joke about "the Blacks" being a family of White people had. Me. Rolling.) It wasn't "Trump has weird hair that looks funny" (although there was a hair joke in there).
Now, to be fair, the audiences for the Correspondents' Dinner and for a roast on Comedy Central are probably pretty different. But I don't have enough faith in Comedy Central, I guess, to handle Sheen with any sort of depth. And Sheen himself isn't messy in an interesting way, anymore - he's just messy, and it's kind of sad and kind of gross, and his messiness in and of itself isn't funny.
I will say, though, that people will absolutely tune in for this, not to see the jokes, but to see what Sheen does. Is he going to make a speech afterward? Is he going to ... I don't know, streak? Call someone a charlatan? Just scream "WINNING" at the top of his lungs and run off the stage flapping his arms? I won't watch it (or Two and a Half Men, that show is totally not funny), but I will almost certainly YouTube highlights from it on the 20th.
*I keep hoping that the latest piece of gossip about Winehouse will be that she's going into detox and rehab for three months, getting all new friends and management, moving to a small town in the English countryside somewhere with few negative influences, and re-dedicating herself to her music. I bump "Back to Black" ALL THE TIME. If/when she puts out another album, I will be all over it. Please get some help, Amy, and keep making music.