A montage of Sheen's film and television work were featured, though due to legal reasons, clips of his tenure on Two and a Half Men were never used. Seth MacFarlane made his third appearance as the roastmaster. Brooke Mueller, Aaron Paul, Corbin Bernsen, Duane Chapman, Michael Boatman, Kristin Cavallari and Richard Kind appeared in the audience. Sheen's famous family members, Emilio Estevez and Martin Sheen, were unable to attend as they were promoting their film The Way, although Martin appeared in a commercial for the roast, spoofing his film Apocalypse Now. During an interview on The View, Sheen's ex-wife, Denise Richards stated that she hadn't been invited to appear and, while she thought roasting her ex-husband could be humorous and that he would be able to take it, she feared it would have a negative impact on their daughters.
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Harvey Levin from TMZ.com was scheduled to appear but ended up not doing so.
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Slash made an appearance playing his guitar during Sheen's entrance. Roasters included Mike Tyson, Jeff Ross, Anthony Jeselnik, Steve-O, William Shatner, Kate Walsh, Jon Lovitz, Patrice O'Neal and Amy Schumer. The roast was taped in Los Angeles on September 10, 2011, and was broadcast on September 19, 2011, exactly one hour after the premiere of Ashton Kutcher's first episode of replacing Sheen on Two and a Half Men. This was also the first time someone served as roastmaster more than once, as Seth MacFarlane also roasted David Hasselhoff. This roast was dedicated in memory of Greg Giraldo. Mike "The Situation" Sorrentino was highly criticized for his performance as a result, Comedy Central pulled several of his jokes from the television airing of the roast. Several roasters paid respect to Greg Giraldo, a Comedy Central Roast regular, who died on September 29, 2010. Jokes were also made about Jeselnik's fame (or lack thereof), Matlin's deafness, King's age, and Jersey Shore. The roast consisted of jokes toward Trump's hairstyle, his show The Apprentice, and his family. Melania Trump, Ivanka Trump, Ice-T, Russell Simmons, John Legend, Lindsay Lohan, and David Foster were in the audience. Roasters included Whitney Cummings, Lisa Lampanelli, Jeffrey Ross, Marlee Matlin (interpreted by friend and business partner Jack Jason, and later a surprisingly appereance by Gilbert Gottfried), Anthony Jeselnik, Larry King, Snoop Dogg, and Mike "The Situation" Sorrentino. The Comedy Central Roast of Donald Trump was originally taped on March 9, 2011.