Did you get Kristen Wiig onboard?
Craig called me and said “What about Kristen?” And I said, “Oh, duh.” To be honest, when we were doing this was during the time when Bridesmaids came out, when the part of Maggie [Wiig's character] fell through and we had to find another Maggie. I was like, “Kristen is shooting all these other movies, she’s not gonna be available.” It was very sweet, Kristen called me and said, “Hey, I read Skeleton Twins, I really like it. I’d like to do it, but only if you’ll have me.” I was like, “Are you joking? Of course.” It didn’t even dawn on me until later that, oh yeah, we have this brother-sister relationship.
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The majority of the conversation we had about Milo was, “Why is this guy self-sabotaging himself?” You know, “What’s he trying to get from Rich,” the Ty Burrell character? [Editor's note: A teacher Milo had a relationship with in high school.] It’s the first person he’s ever been in love with and that’s why he lies to him about being a writer and how he’s on a writer retreat because that’s the student-teacher relationship they had. It’s trying to get that out of him, because that acceptance from Rich that he really wants is love. He just needs that. And then it’s sweet because he ends up getting it from his sister in a harsher, real way. He goes there for the ex and he ends up finding his sister. That’s what Craig always said: “I kind of see this as a love story between a brother and a sister.”