The Songs of Crazy Ex-Girlfriend: Stubbornness Through Song

Crazy Ex-Girlfriend’s Rebecca (Rachel Bloom) solves her problems with three things: fiscal irresponsibility, overreaction, and songs. In “Is Josh Free In Two Weeks?” Rebecca’s frantic scramble to plan a wedding in two weeks encompasses all of the above. This season has had its ebbs and flows, but now the tides have hit the mutual cap of its characters’ persistent refusal to learn from mistakes. The pressure has begun to build.

This stubbornness is partially helmed by Rebecca’s sexy, health-nut boss, Nathaniel (Scott Michael Foster), who accidentally poisons himself with some bad kale. After a roll of shame to the bathroom because of self-soiled slacks, Nathaniel still refuses to take a sick day. One replacement suit and nap-focused pep talk later, Nathaniel’s masculinity needs reassurance. So, serenading a dysenteric man dressed in a hand-me-down suit two sizes too big, Darryl (Pete Gardner), Tim (Michael McMillian) and Jim (Burl Moseley) unleash some questionably gendered hair metal.

The huge wigs, heavy makeup, and low-cut shirts that accompany their shredding are the perfect personification of the mixed gender norms of the “Man Nap.” Darryl uses the mic stand as a penis while talking about the loss of testosterone that accompanies aging, strutting his stuff while emasculating said stuff. The song’s focus on repositioning “manly” things (a suit jacket becomes a blanket, a double-rider motorcycle jacket becomes a sleeveless leather vest) is the same sort of impetus that married glam to metal. Mötley Crüe, Stryper, and Def Leppard lived this strange balance between hyper-feminine and hyper-masculine that wasn’t the beautifully flamboyant androgyny of David Bowie, but the loud bluntness of electric sex.

The song ends its celebration of both naps and men (the series’ complex, nuanced depiction of men, that is) with three sleepy, pillow-wielding rockers dozing beneath three trees set ablaze by their concert’s pyrotechnics. Destruction may be something natural to both sexes, but so are naps. Metal is just how they have to sell it to someone that’s the kind of surface-level bro Nathaniel purports to be—the same way less progressive rockers understood and approached less binary gender roles thanks to Twisted Sister or Kiss.

When the co-worker trio closes Nathaniel’s office door, they’ve both nurtured their boss and had a professional boon with someone that’s intimidated them since his introduction to the company. It’s a mix of typically gendered emotions and successes that mirror the musical accompaniment.

When Rebecca finally breaks under the pressure she’s put on herself (mostly by kissing Nathaniel in the elevator in “Josh Is the Man of My Dreams, Right?”—c’mon, girl), she bursts into song looking for validation. A series of pleas to the harried deliveryman, Patrick (Seth Green), “Tell Me I’m OK, Patrick” is a piano ballad that notably lies in its visuals. Bearded Seth Green’s slight frame (in all its cargo-shorted glory) replaces Rebecca’s atop a piano, much to his surprise, as the ballad continues and the camera ogles him as it would any starlet.

They both ascend the musical dais, leaving the piano to be played by a Sesame Street-esque FedEx package in one of the best visual gags of any number this season. Juxtaposed with a glamorous Rebecca in dangling earrings, up-done hair and an elegant red dress, Patrick is just a normal guy in this fantasy—he doesn’t have to be impressive to have his lack of outward worry impress Rebecca. Her desperate need for reassurance allows her to belt until stubbornness finally takes as much a toll on her as it does on Nathaniel. They both lie exhausted at the end of their numbers, beaten into unconsciousness by themselves.

Their rewards are the terrible pasts they’ve failed to escape. Nathaniel’s overbearing dick of a dad and Josh’s (Vincent Rodriguez III) overbearing ex, Valencia (Gabrielle Ruiz), surge back into the protagonists’ lives with a vengeance. It may look fine for now, but there’s no way it’ll go well. Will this disaster explode, or really explode? And what possible songs could there be? Will there finally—finally!—be period sex? Will it be between Rebecca and Nathaniel? I can’t wait to find out.

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Jacob Oller is a writer and film critic whose writing has appeared in The Guardian, Playboy, Roger Ebert, Film School Rejects, Chicagoist, Vague Visages, and other publications. He lives in Chicago, plays Dungeons and Dragons, and struggles not to kill his two cats daily. You can follow him on Twitter here: @jacoboller.