With his character expected to be killed off in the season premiere of CBS' Two and a Half Men to make way for Ashton Kutcher, Sheen is hoping to make a killing on a rival network.
Yes, Comedy Central has scheduled its upcoming roast of Sheen to go head to head with his former sitcom's season premiere on Sept. 19.
But will it be a "winning" strategy?
"You could say I've been providing kindling for this roast for a while. It's time to light it up. It's going to be epic," a confident Sheen boasts in a statement.
"It's definitely fortuitous timing for us," a rep for the cable channel tells E! News. "Everything aligned. The Daily Show and Colbert are dark that night and yes, you have the premiere of Two and a Half Men."
There should be plenty of fodder, considering the headlines Sheen made in the spring going mano a mano with Men mastermind Chuck Lorre, prompting Sheen's eventual termination and plenty of billable hours for the lawyers.
But unlike the ultimately tame potshots he took at Lorre & Co. during the Torpedoes of Truth tour, Sheen is promising lots of troll-targeting when the roast tapes in Los Angeles on Sept. 10.
"Charlie has assured us that nothing will be off limits in this roast, which scares even us," says a network spokesman.
And speaking of off limits, reports that Brooke Mueller wants her name kept out of the roast are unfounded as of right now, as a Comedy Central rep tells us that the network has received no legal letter from Mueller just yet.
If the success of past roasts is an indication, it should be appointment viewing for the cable net—though it's unlikely to come anywhere close to Two and a Half Men, which averaged 12.7 million viewers last season and should at least attract some initial looky-loos who want to see how show producers write out Sheen and introduce Kutcher.
By comparison, Comedy Central's roast of Donald Trump attracted 3.48 million in March and its 2010 David Hasselhoff-skewering drew 3.51 million. The net's highest-rated roast came courtesy of Jeff Foxworthy in 2009, which drew 4.4 million viewers.
Meanwhile, Sheen's ex-wife Brooke Mueller has let it be known that she better not be roasting material.
Sources in her camp have told TMZ that she is demanding the topic of her ill-fated marriage to Sheen and her own stints in rehab be "completely off limits," claiming the terms of their divorce settlement prevent Sheen from slamming her in public. Mueller's concerns are so great she's reportedly considering having her lawyers send a cease-and-desist letter to Comedy Central.