Chicago is the troubled actor's second stop on his tour. He opened in Detroit Saturday night to awful reviews. Many fans left in the middle of the show.
On Sunday night, Chicago fans were a bit more forgiving, and some went as far as calling Sheen's act good.
The actor showed up at the Chicago Theatre in a tour bus about two hours before showtime and was greeted by cheering fans. Escorted by one of his "goddesses," the actor handed autographed t-shirts to fans.
Jessie Ramirez got one and she isn't even a fan -- just a tourist from Texas.
"We were passing by and looking for fun stuff to do. I started asking people why they were here, and they said, so we stopped to meet him," Ramirez said.
Despite getting booed in Detroit, Chicago fans were more than willing to give Sheen a chance, even paying top dollar.
When asked how much he paid for a ticket to Sheen's show, one man said: "I'd rather not say. I got it off eBay, actually."
"I really feel like he gets a bad rap. I'm kinda on his side," Melanie Bemben said.
Besides sympathizing with Sheen, there were all kinds of reasons why tickets sold out in minutes for the show.
"I'm here to embarrass my mother," said one woman.
"He's so bad, so awful, so absolutely wrong that occasionally an event like this, you have to go see him," said Keith Lord.
Lord and his son dressed the part, as did Nancy Amesquita.
"What possessed me to dress like a tiger? Tiger blood. This is what he represents," Amesquita said.
The show's start time was 8 p.m. Sunday but Sheen didn't take the stage until 8:20 p.m. He received a standing ovation and the fans booed Detroit, so the actor trashed the Motor City. Next, Sheen talked about his messed up life for a half hour and took a break. Some fans had enough while others stuck it out and waited for him to return.
"It's really cool. He is a down to earth guy. He's not ranting and raving like everyone's expecting him too. He's being Charlie, telling it like it is," said fan Jerry Mrase.
"I read the reviews about last night. I was really worried to show up. It's been really good so far, amazing, I think he is really," one woman said.
Sheen went back on stage at 9:30 p.m. and talked about the most random person he ever partied with.
Some fans paid hundreds of dollars for a ticket to the show, which sold out in 18 minutes. When a Detroit fan booed his performance Saturday night, Sheen said, "Sorry dude, already got your money."
Sheen's next stop is Cleveland on Tuesday.