Charlie Sheen Wendy
Credit: Charlie Sheen on Wendy Williams Show 9/19/11

Remember that time last night at the Emmy Awards when it seemed like Charlie Sheen was sincerely trying to make amends? Remember how he agreed to do a Comedy Central Roast (airing tonight at 10 p.m.), suggesting that he just might have a sense of humor about himself? Well, Sheen made the latest pit-stop on his “let’s try to salvage a tiny thread of my public image” tour Monday morning, and the results were… well… mixed at best.

Sheen stopped by The Wendy Williams Show for a sit down with the intrepid journalist, who grilled him not only on Two and a Half Men, but on two decades’ worth of romantic misfires. Unsurprisingly, the latter was not the best topic of conversation. While Sheen seems to be capable of expressing remorse for some of his crazier antics, he is still clearly unable to approach his romantic history with anything other than a flippant, self-deprecating manner that really comes across as cockiness.

To be fair, parts of the interview went remarkably well. He seemed to be sincere when he versed his feelings about the Two and a Half Men situation, and won the audience’s favor when he voiced his support of Ashton Kutcher. “I would just give him a hug and just say, ‘Make me proud, bro,'” he said. “Awwwww,” the audience replied. He also admitted that some people just should not be married, and that he is definitely one of them. He shook his head at the ridiculousness of his Sober Valley Lodge, and admitted that he did not, in fact, have sexual relations with 5,000 women. Progress not perfection, right?

Unfortunately, the good news stops there. While Sheen is definitely trying to make amends with his former TV family, he still can’t seem to face his terrible past with women. When Williams brought up his romantic past, he answered her questions uncomfortably with gibes instead of using the valuable opportunity to apologize.

Shooting Kelly Preston? Not his fault! “Maybe she was trying to commit suicide to get out of the relationship,” he joked. His failed marriage to Denise Richards? Well, she’s great, but “a couple of things I don’t do well — marriage and drinking!” His highly publicized relationship with “Goddesses” Rachel Oberlin and Natalie Kenly apparently wasn’t a relationship at all. “It was really an experiment,” Sheen explained. “Just seeing if you could keep two women together peacefully under the same roof. It’s really hard. Unless they’re lesbians, you know?”

Yikes. Yes, he was trying to be funny. And yes, he seems to be a lot better than he was six months ago. But these “jokes” (which don’t seem nearly as bad on screen as they do on paper) are perfect fodder for anyone looking for an anti-Sheen headline. His history with women is violent and disgraceful, and if he’s ever going to win back even a portion of the public, he’s going to have to try for sincerity and apologize… even if it is on The Wendy Williams Show.

Watch him sound off on his failed marriage to Richards below, and let us know what you thought of the interview in the comments. Unfortunately, this clip does not contain the best part of the interview, when Williams called Sheen a cross between “Larry the lovable neighbor” from Three’s Company and Quagmire from Family Guy. Giggity?

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