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How Crazy Ex-Girlfriend re-met Greg

Rachel Bloom (left) and Skylar Astin
Photo: Robert Voets (The CW)

Crazy Ex-Girlfriend has never been shy about acknowledging the fact that it’s a TV show. In fact, peeling back the curtain to acknowledge the artifice has been one of the most reliably entertaining tools in a crowded toolbox. It’s yielded a seemingly endless supply of recurring bits, self-aware title sequences and theme songs, breaks with convention, direct addresses to the audience, and entire musical numbers that basically mirror what its audience might feel about a new character.

For a year or two, “Who’s The New Guy?” and its inevitable reprise were the most extreme example of Crazy Ex-Girlfriend’s meta streak, but no longer. With “I’m Not The Person I Used To Be,” the series reintroduces Greg, a central character from the show’s early seasons. When last we saw Greg, he was headed off to business school, and played by Santino Fontana. Now he’s back “for the rest of the series… of holidays,” and played by Skylar Astin (Pitch Perfect).


Showrunner Aline Brosh McKenna, co-creator Rachel Bloom, and the rest of the show’s creative team weren’t content to merely wink at the audience about Greg’s new face. Instead, they made it an integral element of the storytelling, using the recasting as a jumping-off point to explore themes or personal growth, perception, the evolution of relationships, and more of the delicious, sticky psychological stuff the series is so adept at exploring. The A.V. Club spoke with Brosh McKenna about Greg’s return, what the future might hold for him and Rebecca, and Astin’s ability to wriggle his way into the Thanksgivings and escape-room outings of a tight-knit cast.

The A.V. Club: At what point after you knew that Santino Fontana was leaving the show did you decide that Greg would return?

Aline Brosh McKenna: Greg left the show earlier than we had intended, obviously, because Santino wanted to go back to New York. While we had always planned for [Rebecca and Greg’s] thing to go amiss when it did, we hadn’t really ever planned to have his character leave entirely. And so we did our best to really wrap up the first part of their storyline in a satisfying way.

Then as we were planning out this last season, we started thinking about that character again, and his relationship with her, and it really did seem like since this is a season where we’re returning to things that she’s left open, we started talking more and more about him. Since we had written off a version of him, could we bring back a different version of him? And if we were going to bring back a different version of him, it [would be] exciting to have him played by someone totally different. Because the show plays so much with perceptual things, with the way Rebecca sees the world—it’s a very much a first-person show—it started to seem fun and exciting.


At first it was just a notion. Rachel and I work hard on the show in between seasons, and then we got captivated by it, and then we got excited to see to see him again, and to see what it would be like.

He’s been gone for a long time, and he’s been in recovery for two years. So he would be substantially different in certain ways, so much so that he might seem completely different to her.


AVC: Skylar and Rachel went to college together—when you started thinking about who might play the role, was Skylar always someone you had in mind or was there a broader casting process? 

ABM: When we thought about it, he was like our dream person. We thought, “Wow, if we could get him that would really be great, and would work great,” and then we just were lucky that that we got him!


AVC: How did having a new actor step into the role change the writing process for Greg’s character? Does it feel like it’s coming from the same place, or is it a different experience?

ABM: He’s still Greg-y, and one of the points that we make going forward is that he’s still the same person. Your personality doesn’t change because you get help. So we wanted to really make that point. Later on, you’ll see that she expects him to be so completely different, and he’s not. He’s, in many ways, still the same sarcastic, self-deprecating person.


But at the same time, in many ways, he has changed. He spent two years in recovery alongside people who’ve been through difficult things. He’s been through difficult things [himself]. So, I think it’s expanded his humanity.

AVC: In the world of the show, does Greg seem different to Rebecca because he’s changed, because she’s changed, or some combination of both?


ABM: Well, she thinks it’s because he’s changed and then at the end at the end of the episode, he’s the one who discovers, “Hey, maybe we’ve both changed, and that’s why you see me differently.” And for all we know, he sees a slightly different person, although he doesn’t seem to identify it that way. But I think it is really that they’ve both changed. She’s changed a lot, so her perspective is different, and he does have the feel of a different person.

It was a really fun opportunity, or it turned out to be a fun opportunity that we didn’t realize [was possible] at the time [Fontana left the show]. Just to recast the character and really deal with someone seeming so different. When you run into an ex, they often seem so incredibly different as to be unrecognizable. And that was something that we thought was funny off the bat.

Rachel Bloom, Skylar Astin
Photo: Robert Voets (The CW)

AVC: There’s a long history in film and TV of roles being recast, but I’ve never seen it integrated into the plot in the quite so direct a manner, both in terms of the actual action of the episode, and also what’s going on thematically and emotionally.


ABM: That’s what got us excited about it! It seemed fun, and keeping in tone with what we’ve been doing.

AVC: Do you imagine that inside Greg’s head, Rebecca is suddenly played by Evan Rachel Wood or somebody?


ABM: [Laughs.] Oh, no. No, I don’t think she looks different to him. I think that she seems different to him, but not so much that she actually looks different. You know, he’s in this recovery process, so I think he’s used to people metamorphosing. And she hasn’t laid eyes on him in that period of time, but he recognizes her right away.

AVC: What was it like to hear a new actor read that character for the first time?


ABM: Oh, it was really fun. I mean, he knows Rachel, he was on a show with Rene Gube [who plays Father Brah on the show, in addition to writing and producing], he knew a bunch of the people on the show. I have to say, for a show that’s in its fourth season coming into that might be intimidating. He just blended right in, just mixed right in with the group, and pretty soon was having Thanksgiving with people, and going to escape rooms. Socially, it was it was seamless.

AVC: What would Greg’s story have looked like without that early exit? 

ABM: Well, we wouldn’t have had him go into recovery, and realize that [he needs help] so quickly. It happens really fast, that he realizes that he’s an alcoholic and needs to get treatment. We did that over four episodes. We had initially conceived that that would happen over [the course of] season two.


After that, with Josh and Nathaniel—with everyone really—some of their stories revolve around Rebecca, but most of their stories revolve around their own personal growth and experiences.

AVC: Like Josh going to therapy.

ABM: We’ve been we’ve been really loving exploring Josh since [he and Rebecca] broke up at the end of season two. So, you know, our plan was always to continue following Greg, and his evolution, and his relationship to Rebecca, and their friendship. We had imagined that he would get into treatment at the end of season two, and then in season three, they would become friends. And so we kind of shortened the first part of it, and then return to it here. We return here to [look at] what what kind of connection they can have as friends.


AVC: So pretty similar, but with a dramatically different timeline.

ABM: Exactly. Santino had a one-year deal, but I think we hoped that things would work out [with] him. So we were going to have Greg and Rebecca break up, but it was going to take slightly longer.


AVC: The big subplots in this episode are about people missing things—Valencia and Father Brah missing their window, Josh missing out on a big part of the high school experience, Paula missing those texts. Should we be looking for resonance with those subplots in Greg and Rebecca’s storyline here?

ABM: Definitely, definitely. The theme of the episode is changes over time, and what people perceived, and what the world has perceived, and what the characters have perceived with the passage of time. So we’ve deliberately put [Greg] in an episode where everybody is dealing with what happens when time goes by, and things have changed, and so we have these two storylines echo, a little bit, the same dilemmas from different lenses.


AVC: It sometimes seems as though Rebecca’s connection with Greg is the most traditionally rom-com-esque in the show, and here we get a song about a series of meet-cutes.

ABM: You know, we tried for three traditional ones. Nathaniel is sort of the unattainable, Mr. Perfect, James-Spader-from-the-’80s, sort of untouchable perfect guy that you’re in love with. Or even like a Richard Gere in Pretty Woman type. Sort of the cold, shut down, unattainable rich asshole. So he’s a trope, too. Greg is sort of a sad sack, best friend, “friendzone” guy. Then Josh is the high school quarterback, hometown hero type. So our intention, as with Rebecca, was to take something that was a stereotype—the crazy ex-girlfriend, and then Paula’s a sidekick, and Darryl’s a goofy boss—and sort of get inside those characters to see what it actually feels like to really live inside those characters. So he’s one of the tropes, but with the love interests, we’re always conscious of exploring tropes that already exist in rom-coms.

Rachel Bloom, Gabrielle Rodriguez, Vella Lovell
Photo: Robert Voets (The CW)

AVC: Are Valencia and Heather right about Greg’s role in Rebecca’s life?

ABM: Well, I don’t know! I mean one of the things that cracked me up about that is that it’s like when you break up with somebody, you’ve been going out for three years, and everybody goes, “Oh my god, thank god,” and you had no idea. It really was funny to us that they had an opinion about it, but they never voiced it because they didn’t want to be rude, and she was pursuing relationships with other people. That’s a good question [to answer] after your last question: He is the one that would seem, to [Heather and Valencia] most like endgame, because they are cut from the same cloth in a way. Nathaniel is sort of a prince charming, and Josh and Rebecca definitely did not sit at the same table in high school. So I think that on the surface, on the face of it Rebecca and Greg are the most externally matched.


AVC: Yeah, it seems as though all of Rebecca’s love interests reflect different aspects of her persona. Like if Nathaniel is sort of the ruthless parts of her, and maybe also the “wow, you’re really broken” and “holy shit, your parents” parts—

ABM: And she’s a little snobby, too.

AVC: Exactly. And then the joyful parts, as well as the self-obsessed parts, are Josh—


ABM: And Rebecca is definitely both of those things.

AVC: So, what about Rebecca is reflected in Greg? What makes them cut from the same cloth?


ABM: I think they’re smart in the same way. I think they have the same—apart from her interest in musicals and rom-coms—references in terms of books they read: Kurt Vonnegut, you know. And I think that that Greg grew up in an environment where he felt like a weirdo because he is an intellectual, offbeat guy who listens to Pogues records or whatever. That’s why I say “externally.” I think when they go to the bookstore, they go to the same section. They have an intellectual connection which is sincere, as opposed to her intellectual connection with Nathaniel, which is mostly based on snobbery and stuff like that.

AVC: Were there any conversations with Santino about the recasting of the role, and where the character is headed?


ABM: We let him know we were doing it. When we decided to bring [Greg] back, we let him know.

AVC: What, if anything, does Skylar Astin bring to Greg that’s new or different from what Santino brought to the role?


ABM: There was always a slight sense, and it was it was how he was written, that Greg was always very neg-y towards her from the second they meet in the bar. He knows that she’s in love with somebody else, and he pursues her, not [in spite of it], but kind of because of it. He’s a bit of a emotional masochist. So he found someone who didn’t really care about him, was looking past him, and now he’s evolved. He’s been confronted with these tendencies in himself. So he’s more aware, and I think it has made him a warmer, kinder person.

And this is less about the actor, and more about the character. I think the character is a warmer, more connected, evolved person who understands when Rebecca tells him what happened with his dad, even though he is understandably disgusted and upset. He also has been in a lot of meetings where he’s heard a lot of people, you know, [who] do too much meth and wind up in ditches. And he knows, with somebody who’s struggling with their mental health, he knows the sort of extremities that they can end up with. So I think his compassion and humanity when she tells him all of that. That’s a different guy. The guy we knew before would have really been excited to punish her. But that’s how we wrote the character. That’s not indicative of the actor.


Skylar himself has a warmth to him which makes him, I think, a natural fit for the recast. His instincts are naturally very warm and kind and connected. And so that makes him a good fit for what we’re writing now.

AVC: Would this Greg ever sing “Settle For Me”?

ABM: Well, he would know that that’s pathological. He would look back on that and say, “Wow, that’s what I thought of myself. That’s what my opinion was. And that’s what I was looking for in a partner, was somebody who made me feel like shit,” because he was at his most self-loathing with her. So he might have the same impulse—I mean, you don’t go into recovery, or go into therapy, and all of a sudden don’t have the impulses. But you can check them. You can examine them, which is what she’s doing. Right?


I mean, in this season, she sees the rabbit holes she used to eagerly bound down, and she sometimes starts going down them, and gets like caught halfway through, but she knows what she’s doing. I always think of when she’s pushing Tucker down the hall, dressed as a busboy, and she’s going, “Wait, this is like the old shit I used to do, this is probably not a great idea, but I have a good reason for it. I’m trying to give this kid the childhood support that I didn’t have.”

AVC: Progress!

ABM: Yeah. So she has an understanding of what she’s doing. An awareness, which is really kind of all you can ask of someone who’s struggling with these issues. And he’s the same. So I think he has a lot of the same impulses, but he’s able now to sort of healthily reflect on them. So I think he might have an urge to sing “Settle For Me,” but he might look in the mirror, and take that to his meeting and say, “You know what? I had an urge to tell this girl she could treat me like shit. That’s probably not the best thing.”


AVC: Is there anything that you can tell us about where this relationship, or the season, is headed?

Well, they’re going to spend more time together and get to know each other. And also he’s going to get to know a lot of the other characters on the show, too. That’s been tremendously fun. And in fact, the next episode could be the kookiest, craziest episode we’ve ever done. I mean, it’s bonkers. That was so fun to make. And I will just say—slight spoiler for that episode—Greg spends most of his time with Nathaniel. So that was another fun thing about bringing him back: We can mix and match him with the other folks, and that’s been great. Especially he and Scott Michael Foster, [who] bonded instantly.


But he and Rebecca are going to try and figure out what’s there, and what’s left, and is there anything. I think you can see in this episode and in episode nine, that there’s a strong connection there. What do you do about that?

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About the author

Allison Shoemaker

Contributor, The A.V. Club and The Takeout. Allison loves television, bourbon, and dramatically overanalyzing social interactions.