When Comedy Central chose Ozzy Osbourne's "Crazy Train" earlier this summer to be the campaign theme for its upcoming "Comedy Central Roast of Charlie Sheen," even Walter Levitt, the network's exec VP-marketing, couldn't have predicted the marketing serendipity that awaited.

Not only would Mr. Sheen agree to appear in a handful of TV ads as the conductor of said "Crazy Train," but reports soon swirled that his fictional alter ego on "Two and a Half Men" would be killed off by ... you guessed it, a moving train.

"It was one of those moments as a marketer where you just feel like the universe is unfolding as it should and aligning perfectly," Mr. Levitt said. "When we started working on the campaign, the notion of making the song 'Crazy Train' the centerpiece was one where we knew we had something when we heard it."

Less coincidental was Comedy Central's choice of 10 p.m. on Sept. 19 as the roast's airtime, the same date as the "Two and a Half Men" season premiere. "The fact that an hour earlier Charlie will be killed by a train is almost too perfect for words," Mr. Levitt said.

The train theme will be rolling out across TV, out-of -home, radio, print and social media in what will likely end up as Comedy Central's largest roast campaign to date. Starting next week, double-decker buses in New York and Los Angeles will be wrapped to look like the campaign's signature "Crazy Train," with an additional train track-themed wallscape going up on Prince and Lafayette Sts. in New York's SoHo neighborhood. On TV, Comedy Central will continue to roll out the latest in its series of train-conductor spots with Mr. Sheen next week, followed by clips from the actual roast after it tapes Sept. 10 in Los Angeles.

On Sept. 15, four days before the roast, Comedy Central will partner with a handful of Clear Channel radio stations in major markets to have Charlie Sheen pre-record introductions of the song "Crazy Train" during key afternoon drive-time music blocks to drive day-of awareness for the roast. On Roast Day, Sept. 19, commuters in New York City will see train tracks on the cover of that day's free morning daily, AM New York, that will lead through to two more pages of train tracks running across editorial, ultimately revealing an ad for that night's event. And guess what song will be playing when the copies of AM New York are handed out?

"When people hear 'Crazy Train,' we want their first association to be with Charlie Sheen," Mr. Levitt said.

If it seems like a whole lot of marketing stunts for one event, there's more riding on it than usual for Comedy Central. Its summer 2011 ratings were down 7% year-over-year among total viewers and 8% among adults 18 to 49 and 18 to 34, according to Nielsen Media Research data from May 31 to Aug. 22 . During Roast Week, Comedy's signature shows "The Daily Show With Jon Stewart" and "The Colbert Report" will be on hiatus. Plus , the network's roasts often rate among its most-watched telecasts, with this spring's Donald Trump roast drawing 3.5 million total viewers and a record number of men 18 to 24. Last fall's "Roast of David Hasselhoff" was the network's fifth most-watched roast, following previous events "honoring" Jeff Foxworthy, Pamela Anderson, Larry The Cable Guy and Flavor Flav.

But due to the roasts' inherently foul nature, sponsors can get skittish -- especially when it comes to a hot-button personality like Mr. Sheen, whose Live Nation comedy tour earlier this year went unsponsored. However, Comedy Central confirmed that Axe and Electronic Arts have signed on as the roast's lead sponsors, with more marketers to be confirmed in the coming weeks.