Greg Serrano was recast in Crazy Ex-Girlfriend season 4 because the creators wanted to tell a different story. Created by Rachel Bloom and Aline Brosh McKenna, Crazy Ex-Girlfriend blended elements of romantic comedies with musical dramas. The series initially focused on the story of Rebecca Bunch (Bloom), a lawyer who moves from New York City to West Covina, CA, in order to pursue her high school sweetheart. One of the lowest-rated shows in television to be consistently renewed rather than cancelled, Crazy Ex-Girlfriend garnered glowing reviews and a devoted fanbase thanks to its incisive humor and the way it approached the subject of mental illness.
In Crazy Ex-Girlfriend’s first two seasons, Santino Fontana portrayed Greg Serrano. Battling with Josh Chan (Vincent Rodriguez III) for Rebecca’s affections, Greg was often overlooked since Josh was the idealized ex-boyfriend that Rebecca was in pursuit of. Having only been contracted for one season, Fontana opted to leave the series and turn his attention to other career opportunities. As a result, Greg was written out of Crazy Ex-Girlfriend near the beginning of season 2. It was explained that Greg would leave West Covina to attend business school at Emory University. Partly, as Greg himself elaborates in a heartfelt song just before he exits, it’s also a way for the character to escape his unhealthy relationship with Rebecca. Greg eventually returns in a recurring capacity for Crazy Ex-Girlfriend season 4, appearing in 10 episodes of the final season, but he’s played by an entirely different actor.
McKenna and Bloom wanted to tell a different kind of story, and so they recast Greg with Skylar Astin, with him portraying a “reimagined Greg”. Not simply shying away from the recasting situation or making a passing joke of it as comedies like Roseanne have done, Crazy Ex-Girlfriend turned Greg’s recasting into a key plot point. Bloom explained at the time that the intention was to make a statement on how the perception of those around us can change depending on the circumstances.
The way Greg’s recast played out was that, when he returned, Rebecca was the only one who believed his appearance had changed. To Josh, and to the rest of Greg’s friends, nothing was out of the ordinary. The idea was that Rebecca had been perceiving Greg differently during their tumultuous interactions in the first two seasons. Given the fact that Rebecca was in a better place emotionally in season 4, and given how Greg was also improved as a person, she could see him the way others always had. Although it’s less literal, Rebecca’s perception of Josh similarly shifted throughout the series. At first, he was the perfect yet unattainable romantic partner. Then, when Rebecca was disillusioned by him, Josh turned into a complete villain. Finally, in Crazy Ex-Girlfriend season 4, Rebecca saw correctly that Josh was just a regular guy with both positive attributes and flaws.
McKenna and Bloom noted that they informed Fontana of what they were planning to do with Greg and, for his part, Fontana was effusive in his praise and support for Astin taking over the role he originated. Fans have debated over which portrayal was best, though both actors, Fontana with his Broadway credentials and Astin coming off his memorable turn in the Pitch Perfect franchise, brought unique aspects to their performances. Recasting a familiar face can be extremely tricky, but Crazy Ex-Girlfriend handled it with a funny and thought-provoking storyline. It’s one of the many ways the series remains underrated.