Rachel Marie Oberlin, better known by her porn pseudonym Bree Olson, dated Charlie Sheen for six months during his Two and a Half Men dispute. Along with Natalie Kenly, Olson served as one of Sheen’s live-in girlfriends—or “goddesses,” as he famously called them—at his home, which he nicknamed Sober Valley Lodge. She was by Sheen’s side as he spiraled downward, from his infamous radio rant against Men creator Chuck Lorre to his Violent Torpedo of Truth tour. Then, in April, she broke up with Sheen and removed herself from the media whirlwind.
Prior to her stint as Sheen’s girlfriend, Olson, 24, was one of the most sought-after actresses in the adult film industry, appearing in more than 170 porn films. The Indiana native even had a cameo on the E! reality-TV series Keeping Up With the Kardashians, as a sexy nanny who was fired for wearing bikinis to work. In an in-depth interview with The Daily Beast, Olson opens up about her relationship with Sheen—from his courting her in her home state of Indiana to their breakup, how Keeping Up With the Kardashians is scripted, her porn career, and her decision to quit the adult industry and become a legit actress.
How did you get the name “Bree Olson”?
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I went to high school with a chick named Bree who was super, super hot, so I was like, “OK, let’s go with Bree.” Then, when I got more popular and got an agency, they said I needed to pick a last name. It was either Bree Dupree or Bree Olson. I decided to go with Bree Olson because everyone says I look like the “Olsen girl next door,” so I wanted to do a wholesome type of thing. And I watched the Olsen twins on Full House and I’ve always loved them, so that was part of it.
And you were at one point studying to be a doctor. How did you go from being premed to porn?
I went to Purdue University for two years premed. I had always wanted to be a doctor. I was going full time and I’m a student working 40 hours a week because I didn’t have any support from my parents because they weren’t financially well off. It was a lot for me to deal with. I always had interest in the adult industry, so one day I just Googled “Porn Application.” Sure enough, this website came up and I posted all my pictures and information.
What were you known for in the porn industry?
I was known for being the dirty girl. I had a really dirty mouth, so I could dirty talk like no other. I didn’t even do it purposely. People just started complimenting me on it. It always turned me on to talk, so then I just embellished it even more for the movies.
There’s the old cliché that all porn stars had traumatic childhoods. What was your childhood like?
I do remember when I was a young girl I would have my Barbie dolls have sex with each other. I was just so sexually curious. I guess I just had it to a greater extent than most people do. My sexual drive is insatiable. I’m such a horny pervert! My classic line is, I have a dude’s mind in a hot chick’s body. That’s basically how it runs! All I think about all the time is sex. But everyone at some point has been bullied at school or gotten into a fight with their parents. We’re just like everyone else.
And I heard that you’ve since quit the porn industry?
I haven’t done anything in the industry since Charlie, and after I broke up with Charlie I was thinking about getting back into the industry. We have to get tested once a month, and I was in the testing center and I was just sitting there and thought, “You know what? I’m not going to do this. I want to be mainstream.” I’ve worked since I was 12 years old, when I was detasseling corn, so if I put my mind to it I know I can do it. I want to be in blockbuster movies. The sky is the limit.
You did have a brief brush with Hollywood when you appeared on an episode of Keeping Up With the Kardashians as the children’s hot babysitter.
It was cool. It was different. It was in their first season and everyone was really nice. It was scripted, so I was hired because they couldn’t find a legitimate actress last minute that was willing to take her clothes off. And there’s one scene where I took my bikini top off, so they just went to my industry and happened to call my agent.
So how did you meet Charlie Sheen?
One of my girlfriends who’s a big party-hopper and celeb-hopper approached me and said, “I’m going to Charlie Sheen’s tonight.” And I was like, “Who’s that?” And she was like, “He works on Two and a Half Men.” I went, and we just sat at a table and talked for hours and things went really well, and I told him, “I have a flight the next morning back to Indiana.” He was like, “No, just stay. I have girls who party all the time for a few days.” I was like, “I’m not one of those girls!” I ended up going on the flight, and we just continued exchanging phone calls, emails, texts back and forth for months.
And what was it like when you finally met again?
The next thing I knew, he flew his jet to Ft. Wayne, Indiana. So we kept it under the radar. Then all the stuff happened in Vegas. The whole reason he was there is because I invited him out there because I felt bad that he went to Indiana to see me and I hadn’t come to L.A. to see him. So he stayed up in the Playboy suite at the Palms. I went up to the room [after the AVN Awards] and we spent the night.
I remember reading about that infamous Palms party in the tabloids; apparently there were tons of girls and boatloads of cocaine.
There weren’t all these other girls while I was there. He obviously stayed there after I left. I didn’t see any drugs. We just chilled, watched TV, and—this is funny—he invited me to the Super Bowl. We were going to sit in Chuck Lorre’s box, of all people, at the Super Bowl. There was this huge bathtub and I said, “I’m going to take a bubble bath,” and we just had a nice night together and went to bed. Then all the media stuff came out, and this was around the time the tsunami hit, so I was getting ready to leave for a two-week work thing in Japan, and I remember Charlie called me a few weeks before I was supposed to leave and said, “I’m in love with you. Now is the time. Now or never. Come move in with me and be my girlfriend.” I talked myself into it and thought, “Worst case scenario, I can just leave.”
So what was being Charlie’s girlfriend like?
Everything was cool at first. He was taking his month off from Two and a Half Men, so that’s when [his home] was deemed Sober Valley Lodge. When I got there, there was a sober sponsor and a nurse, and we just hung out. Then we took a trip to the Bahamas and took Brooke [Mueller] with us, because he wanted to have Brooke and Denise [Richards] move into the same neighborhood he was in so he could be with all his kids. He and Brooke got in a fight the first night, so she got sent home. Then, the next morning, he did that radio show and went on his notorious tangent about Chuck Lorre.
What was it like being there for that?
I’m sitting right next to him and I just have my jaw dropped open. I’m like, “You’re kidding me.” After he got off the phone I’m like, “We need to apologize!” But we immediately flew back home, and then it turned into a crazy media circus. And Charlie is just saying all this stuff and I felt like I was the only one in his corner, since everyone is such a yes man around him and I wasn’t dependent on him. It was so frustrating to me because everyone was saying, “Yeah, Charlie, you tell ’em!” It was devastating watching the boyfriend that I love be the highest-paid TV actor in the world and taking that all away by doing all these interviews. Then the tour people came around, and all they have is their tour interests in mind. And I’m like, “You don’t go from being an A-list celebrity to doing this tour!”
When did the relationship go south for you?
Well, people I knew would say, “You’re usually so vibrant and vivacious, but in interviews you seem so quiet.” And I was like, “Yeah, I was miserable and just waiting for it to end.” We had adjoining rooms and me, him, and Natalie never slept together at the same time, and this one night I was in the other room and it was spur of the moment. I got a piece of paper, packed my stuff, and wrote him a note: “Charlie, I’m not comfortable here anymore. I wish you the best on the tour, but I got to go home.” I left him his watch. But Charlie and I have always remained cool. People are trying to compare me to Capri Anderson or Kacey Jordan, but those were hired hookers. I was his girlfriend for six months and I didn’t bash him. Those girls made him look like a horrible person, and he’s not. I just wanted to defend him.
You recently did a brief interview and pictoral for Playboy where you shared a little bit about your sex life with Charlie.
Is he a rock star in bed? Well, yeah, he’s had a lot of f'ing practice. And I said our favorite position was missionary, and people are like, “I can’t believe you told Playboy all this stuff!” And I’m like, “Everyone’s favorite position is missionary!” But we still talk and text, and we’re cool.
He seemed very angry throughout the whole ordeal and clearly not himself.
He and Chuck have had this rivalry for a long time, and Charlie would put up with it, and Chuck would take stabs at him with the vanity cards, and finally he just blew up. We would also sit in bed and watch his old interviews, and he’d be saying, “Oh, I believe in AA.” He’d be watching yelling out, “LIAR! LIAR!” He was just doing those interviews to appease the public, and he was so fed up he just stopped acting and giving people what they wanted.
Now that you’re taking on Hollywood, what sort of acting work would be ideal for you?
I’m a total True Bee! True Blood totally inspired me, and when I watch the show, I say to myself, “I could be a character like Sookie.” I wouldn’t ever want to take over her part, and it wouldn’t be True Blood without Anna Paquin, but to be a Sookie-type character on another series is what I would love.
And I heard that you’re a vegan.
I’m a vegan and proud!
You know that’s going to open you up to all kinds of jokes.
I said on my Twitter, “You guys, your meat jokes are retarded! You’re not clever, so please stop saying it.” I would seriously get like 30 of them a day! I’m not a porn star anymore, so they can shove it!
Is there anything else you’d like to tell me?
I love my little kitty, Dr. Sniffles. I was premed at the time, so that’s where the doctor part came from, and Sniffles, I just thought it was cute. I was like, “What can she cure?” And she makes me happy, so she cures sadness.
