So when I was trying to explain to Tim what this would be, it’s very hard to explain, but I knew that he would get it, and understand why it was funny. Because if he could handle [that Grinder] premise, he can handle any premise. [Laughs.] There’s nothing weirder than that.

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He was the right guy for 500 reasons, but largely because, as a performer, he has this effortless calm about him, in the way that he engages with his work. That’s what was exactly required for this bananas idea we that we were letting out.

AVC: A lot of people probably still see him as Raylan, or they see him as Bullock from Deadwood, but he’s also done these great screwball performances on The Grinder and Santa Clarita Diet.

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MS: He has this consistency, no matter what tone he’s in the middle of. I remember seeing Go and being like, “Who the fuck is that guy?” He was so good and he’s a total heavy at the beginning of the movie, but then he gets some real comedy scenes. Like in the scene where the gangster guy is about to shoot that guy through the arm in retribution for having been screwed over, and Olyphant is there, and he’s really into it in a weird way, but he’s freaked out about the mess. [Laughs.] And he’s laying out that they first think he’s the guy that they want. And then it smash cuts to him drawing a map, like “Here’s where you want to go.” He’s just completely unflappable in every role he does. I’m a huge fan. That’s the No. 1 reason he’s on [The Good Place]: I just love the guy and think he’s an incredible performer.

AVC: Was there ever any talk of having him done up like Bullock, or would that have been too complicated?

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MS: The key is “What does The Judge want?” We just felt like Raylan is more her speed. When I was explaining the role to Tim on the phone, he said, “Am I myself, or am I Raylan?” And I said, “No no no: You’re you, but I think you’re edging toward the Raylan side of things. And he went, “Full Stetson?” And I was like, “Yeah, I think Full Stetson sounds right.”

But then, as I said that, I was like, “Oh, I have to ask for permission for this. I want him to look like Raylan, he’s going to be acting a little like Raylan.” I don’t know [Justified showrunner] Graham Yost, but I got in touch with him and asked for his blessing and he very nicely gave it. Which made me feel like, “Okay, as long as Graham Yost is okay with this, then I’m okay with it.”

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AVC: You mentioned that you knew Tim beforehand—how did you first connect?

MS: It’s kind of a complicated story. I’ll give you the shortest possible version: I was such a fan of his from Deadwood, and I talked about Justified so much. And I wrote a thing for Vulture in Justified’s last seasonVulture does this year-end awards thing, and they asked me to judge the category Most Quotable Dialogue, and I was like, “I’ll do this if I can give it to Justified.” If you’re talking about line-for-line dialogue, I feel like that was the best dialogue on TV. And I was talking to my wife [Single Parents showrunner J.J. Philbin] about it, and my wife said, “If you ever leave me, it’s not going to be for another woman, it’s going to be for Timothy Olyphant.” [Laughs.] And I said, “You know what: You’re probably right!”

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So my 40th birthday, my wife made a video for me of all these different people saying “Happy birthday.” And one of them was Timothy Olyphant—whom I had never met. She’d gotten in touch with him through her agent and he sent me this long birthday message, the crux of which was “I’ve heard you have a crush on me and you’re deeply in love with me, and that’s very flattering.” And it was amazing. I then got his email address and wrote him to thank him and sent him the thing I’d written about his show, and said “I don’t know if you ever saw it, but I wrote this about your show because I was a huge fan.” And then that started an email correspondence, then we eventually met each other and hung out a little bit and talked about TV and stuff like that. It came more from me just being in love with him. [Laughs.]

AVC: There’s more than a little bit of you in Judge Gen’s reaction to this, then?

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MS: A hundred percent. Generally speaking, Judge Gen’s reaction to him is my reaction to him as a presence in the room.

AVC: Do you think the joke would still land if “Timothy Olyphant” weren’t such a fun, “Eleanor Shellstrop”-like name to say?

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MS: It didn’t hurt. As you can tell by the way people react to him, they’re constantly saying his name. Like Gen said, “You made me an Olyphant?” which is a very funny thing to say. My favorite thing in the episode is something he just improvised, which was he asks a question, Eleanor says, “Yes, good question Timothy Olyphant.” And he goes, “Tim’s fine.” [Laughs.] That was just him, in that moment, goofing around, and we left it in because I thought it was funny.

AVC: If Tim wasn’t available, which of The Judge’s other TV crushes would you have considered? Was Mark Harmon in the mix?

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MS: He was brought up. And then we thought about Kyle Chandler, because I think the first TV show she ever said she’s watching is Friday Night Lights. Tim was the first guy we called, so luckily we didn’t have to go to any backups. Mark Harmon, Kyle Chandler—she has a type, Judge Gen does. Right? The tall, dark, and handsome type. Luckily we got our guy.