Ryan recalled on the Office Ladies podcast landing her Holly Flax role soon after her Oscar nomination for Gone Baby Gone. Turns out, Ryan and executive producer and cast member Paul Lieberstein worked together on the ABC sitcom The Naked Truth. "It was so soon after the Oscars and I was like, 'You know, I'm doing a lot of dramas. And if I have any kind of cachet right now, at this moment, I want to do a comedy — and I want to do a comedy like The Office,'" Ryan recalled, according to Mashable. "My agent had kind of reached out and at the same time Paul had reached out, I guess, to him. I don't know who got there first, but it was I really think it was like about the same week. Paul had mentioned that he was also a fan of The Wire, as were some of the other writers. So it was kind of a culmination of all those worlds coming together." What was it like for Ryan to work with Steve Carell? "You know, always with Steve, it was so hard not to laugh. It was also like a thrill that sets in," Ryan said. "Look, I remember when I was 25 I went skydiving, and I did it where you're strapped to the other instructor. And just as the airplane door opened up and he made me look out, we were about 13,000 feet in the air. And I remember the thought in my head is, 'OK, I'm going to die or I'm going to have the time of my life, pick one.' And I remember picking I'm going to have fun. And as nervous as I was, you know, being like in those scenes with Steve, I remember that moment too. Like, 'Oh, just pick one. Why don't you have fun instead, you know?'"