The first time I met Jennifer Aniston, she was naked.

During the rehearsals for the live broadcast version of "Fail Safe" directed by Stephen Frears, I was invited to tour the sets, talk to the people behind the event, and possibly take a peek at some rehearsals. George Clooney was our host for the day, and his assistant at the time, Amy, was the one assigned to drive us around the lot that afternoon.

Amy was the sort of person who knew everyone, and she pointed out a soundstage where they were shooting the Mark Wahlberg film "Rock God." As she was pointing it out, the door to the soundstage opened and Jennifer Aniston came strolling out, wearing the tiniest kimono I've ever seen. Amy waved her over, and the two of them started talking. As they did, it was fairly obvious that Aniston was wearing the kimono and nothing else, and she even made a joke about how odd it was to be introduced to someone like that, playing a quick round of "how much can you see?" with us and making a huge joke out of all of it.

The Aniston we met that day really didn't match the Aniston I've seen portrayed in the media over the years. Talking to her again over the years, she seems very aware of how people view her, and many of her recent choices have seemed to intentionally challenge that public image. We sat down to talk at the "Horrible Bosses 2" junket here in LA, and I decided to address the idea head-on.

"They asked, very sweetly as they were writing, how far they could go, and I said, 'Just go as far as you can, and we'll pull back if we want to.'" Asking her about jumping from the joyful profanity of "Bosses" to the stripped-down and raw "Cake," she said it's that range of experience that keeps things interesting for her, and I asked how hard it is to get filmmakers to think of her in new ways. "I happened to be ready at the time when I did read it, and I remember saying 'I've got to fight for this.'"

From the moment it premiered at the Toronto Film Festival, it seemed clear that the conversation about "Cake" is going to center on the way Aniston put on weight and stripped away all the glamor that is normally part of her on-screen appearance, and in this conversation, it's very clear that she's making choices from a very personal place right now.

"Horrible Bosses 2" is in theaters November 26, 2014, and "Cake" should be in theaters in early 2015.

A respected critic and commentator for fifteen years, Drew McWeeny helped create the online film community as "Moriarty" at Ain't It Cool News, and now proudly leads two budding Film Nerds in their ongoing movie education.