Now theres that sardonic disposition we missed so much! On Friday night, Greg Serrano finally returns to Crazy Ex-Girlfriend—but hes a little . . . different. By that, we mean hes being played by an entirely new actor: Skylar Astin.
The shows original Greg, Santino Fontana, left the show in Season 2 due to scheduling conflicts, temporarily throwing off show-runners Rachel Bloom and Aline Brosh McKennas original plan for the show. The two coped by condensing Gregs intended story line before writing him off. But once Bloom and McKenna had finished Season 3, and started blue-skying the shows fourth and final season, they realized there might be a way to bring the character back. “But since we had done such hard work to sort of write him off completely,” McKenna said in an interview, “the question was: how can we bring him back in a way that was purposeful and made sense?”
Thats when the show-runners came up with an idea: after all this time and everything shes learned, Rebecca sees Greg differently. He is, quite literally, a new man to her—one played, now, by a different actor. “We got excited about it, and then started talking seriously about finding someone else to play Greg,” McKenna said.
Skylar Astin, who starred in Pitch Perfect and TBSs Ground Floor, was the duos first choice—and for good reason. Hes been on Broadway, so they knew he could keep up with the shows singing and dancing demands. Hes also charming, funny, and seemed capable of capturing the original Gregs true essence. As McKenna put it, “There is a nice salty, sardonic side to Skylar in some of the parts that hes played, so we felt like that would work well.” It helped that Astin also knew Bloom from college, which explains the immediate chemistry they share in their first scenes together in Fridays episode.
Although Rebecca experiences Greg differently when they meet again, deep down hes still the same guy, with the same worldview—a realization McKenna said Rebecca will struggle with going forward.
The show didnt have much trouble adjusting itself once Astin was thrown into the mix, even four seasons in. “He has just fit in so well with this cast and this company, I mean, effortlessly—and, you know, is already hanging out with people on the weekend,” McKenna said. “That happened right away.”
Was anyone on the shows creative team worried that fans might not take to the new Greg—that this unorthodox maneuver might be seen as too gimmicky? “You cant really work backwards from that kind of thinking,” McKenna said. “We work from inside the piece and from the story that we want to tell, and we just felt like, dramatically, it was important and interesting for Greg to come back. So we committed ourselves to that—and that opened a lot of avenues up for us.”
“The first half of this season has been [Rebecca] landing on her feet, trying to take responsibility for the things that shes done after the last season, where things kind of skid off the rails a bit,” McKenna continued. “Shes trying to get her life under her, and so we devoted really the first half of the season to her going down that list and dealing with her mother and her half-brother and what she was going to do career-wise. And we felt like wed given her a nice long period of time now since her suicide attempt, so that we could turn our attention to their love story again.”
McKenna refused to reveal anything about which ex, if any, Rebecca might end up with when the show concludes this spring. (“Anything can happen! Weve got a lot of guys in play.”) But really, wherever the show leaves Rebecca in her love life will be secondary to the journey of self-discovery and maturation shes trekked since Season 1. As Rebecca has learned, her life and all of its intricacies amount to so much more than a love story. McKenna also noted that the shows main goal has always been to examine some of the cliches and misconceptions about “crazy” people, and how romantic obsessions can form—a problem she believes is very relatable. “Theres an interior experience of being romantically obsessed,” McKenna said, “and in [Rebeccas] case, it sort of reveals some larger mental issues that she has to deal with. Its really about her working her way through those. And if thats been informative or helpful to people, thats great.”
More Great Stories from Vanity Fair
— The supercalifragilistic Lin-Manuel Miranda
— The Golden Globes are quirky—and thats a good thing
— How The Sopranos gave us Trump training wheels
— Rockos Modern Life was even loonier than you thought
— The years best movies, according to our critic
Looking for more? Sign up for our daily Hollywood newsletter and never miss a story.
Get Vanity Fairs HWD NewsletterSign up for essential industry and award news from Hollywood.Laura BradleyLaura Bradley is a Hollywood writer for VanityFair.com.