by Megan Bailey, Staff Writer

As Empire kicked off as a smash hit in 2015, Crazy Ex-Girlfriend started its cross-country move. The brainchild of Rachel Bloom and Aline Brosh McKenna, with music by Adam Schlesinger and Jack Dolgen, the show took off on The CW, of all places. Lasting a very respectable four seasons, Crazy Ex-Girlfriend took a kooky premise, catchy music, and some lovably flawed characters to the extreme.

Rebecca (Rachel Bloom) moves after she sees her ex, Josh (Vincent Rodriguez III), in New York and finds out that he lives in West Covina, California. In this conversation, he talks about how wonderful the city is and how close it is to the beach (with no traffic, of course). Though they only dated briefly at summer camp, she feels compelled to quit her job at a cushy law firm and move to California. She tells herself, and tells herself, and tells herself, that she didn’t move for Josh, but by the end of the pilot, we see her face the truth: She totally did.

After this move, Rebecca starts her new job at Whitefeather & Associates, where she meets Paula (Donna Lynne Champlin). At first work rivals, the two bond and become friends pretty quickly. And then, when Rebecca discovers that Josh has a girlfriend, Paula helps her plot how to get more involved in his life. Totally healthy behavior!

This concept could very easily pit Rebecca against Josh’s girlfriend, Valencia (Gabrielle Ruiz), and portray Valencia as a vapid woman with no inner life. But while you have more superficial songs from her at the start (“I’m So Good at Yoga,” for example), she’s given a full character with room to grow and become someone other than Rebecca’s romantic rival. By allowing her to stick around after breaking up with Josh, it lets Rebecca—and the viewers—see who she is as a person.

As Rebecca tries to get close to Josh in season one, she meets Greg (Santino Fontana), who is one of his friends and works as a bartender. She presses him for information about Josh while they make out at a party, which is certainly a choice! Over the course of seasons one and two, Rebecca, Greg, and Josh end up in a bit of a love triangle, prompting one of the iconic numbers, “The Math of Love Triangles.”

Rebecca also deals with the ups and downs of her mental illness over the course of the show. Upon moving across the country, she stops taking her antidepressants, convinced that her living situation (and proximity to Josh) will make her happy. Very healthy behavior! But by the third season, Rebecca is diagnosed with borderline personality disorder, and the fourth season puts her on a course to finding herself.

This all sounds pretty heavy, but the tone of the show and its clever songs kept the vibes just right. The cringe-comedy scenes are almost too much for me to handle, but the characters all feel like real people who have real problems. And the musical scenes are so fun to watch!

The music ran the gamut from a ditty inspired by “Do You Hear the People Sing” from Les Miserables, to a bisexual anthem, to an R&B bop about how stressful it is to get ready for a date, and then an eighties-esque song about your hatred of men. The songwriting was strong over the course of each season, and every character on the show got their moment to shine in song. To this day, I pull up “Let’s Generalize About Men” at least once a month because it’s such a catchy song. It’s “a primal ritual we need now and then!”

Another way the show stayed a bit silly is that when Santino Fontana, who originally played Greg in seasons one and two, couldn’t return for the final season, they simply brought in Skylar Astin to play the role instead. The old Greg was surly, an alcoholic bartender. The new Greg is more optimistic and peppy, so the switch sort of makes sense, even if it was simply due to Fontana being unavailable due to his working in the pre-Broadway tryout of Tootsie the musical at the time of filming (and he went on to win a Tony for this role, so that’s nothing to sneeze at).

Between seasons, the cast often did some live shows, and before season four aired, they’d done a tour. Following the series finale in 2019, “Yes, It's Really Us Singing: The Crazy Ex-Girlfriend Concert Special” aired, which featured a lot of the classic fan favorites. Bloom even talked about how hard it was to drill down on which songs to include with only forty-two minutes available for the special.

Roughly a year after the show ended, Schlesinger died due to complications with COVID-19. A musician in his own right, he was in Fountains of Wayne (of “Stacy’s Mom” fame), and he’d written music for a lot of films and television, including Josie and the Pussycats and Music and Lyrics. Famously, he wrote the incredible song “That Thing You Do” from the film of the same name. By all accounts, in addition to being very talented, he was also a great guy to collaborate with. His death in April 2020 came as a shock.

Around that same time, Rachel Bloom gave birth to her daughter, which became a very stressful experience for her due to how little was known about COVID at the time and how chaotic her experience in the hospital was. Bloom goes into this in her show, Death, Let Me Do My Show, and it’s a touching, emotional tribute to Schlesinger and a reminder to tell your friends and family that you love them.

Crazy Ex-Girlfriend is a testament to what a talented group of writers and comedians can do with a kooky concept and a dream. I wish we had more shows that took the kinds of swing this show and its network, The CW, did, and I especially wish we let shows reach fourth seasons more often. Next month, I’ll be writing about a show I really wish had gotten that opportunity: Julie and the Phantoms.