To be honest, it has yet to set in that Crazy Ex-Girlfriend is ending this week. For four years, Rachel Bloom and her incredible band of actors and writers told an original story that lightly lampooned romantic comedies while also having an incredible amount of affection for them. It was one of the best depictions of the millennial dating scene on television, a smart exploration of how our childhood traumas negatively influence our relationships, and a compassionate call for self-care and better mental health support. It was also a musical… and a damn good one at that.
Making a list of the series’ best songs is an incredibly difficult task and, honestly, somewhat pointless. There isn’t any honorable mention for this list because I’ve never actively disliked any of these songs… they always furthered the plot or developed the characters in an intelligent way, even if some are catchier than others. And picking just 10? Just know that this list went through various drafts before finally landing on what feels like the closest possible final form… assuming the final episode airing tonight doesn’t drop another brilliant number, throwing the whole ranking off.
(some spoilers below)
10.) “Who’s the New Guy?” (from Episode 2.9, “When Do I Get to Spend Time With Josh?”)
About halfway through the second season, Crazy Ex-Girlfriend made a huge leap of faith by introducing a whole new male lead into a well-established storyline. How do you sell audiences on this massive change? Well, by singing about it. “Who’s the New Guy?” is a short, silly meta-song that gives many of the show’s terrific supporting players the chance to shine. It also started one of the series’ best habits: selling the audience on clichéd or unbelievable story tropes by having the characters explicitly acknowledge its realism, and then making everyone laugh about it.
https://www.youtube.com/watch?v=k6zP_LE4HFE
9.) “I’m So Good at Yoga” (from Episode 1.2, “Josh’s Girlfriend is Really Cool!”)
Valencia’s character arc over the course of Crazy Ex-Girlfriend, from a stereotypical mean girl to a kind, confident, bisexual badass, proved to be one of the best storylines in the series. But let’s not forget: when we were first introduced to her in the second episode of the series, Gabrielle Ruiz absolutely killed it with “I’m So Good at Yoga,” a musical number so good that Lin-Manuel Miranda even tweeted about it. Ruiz is hilarious and nails the vocals and choreography, while the lyrics (particularly in the uncensored version) are Crazy Ex-Girlfriend at its crudest and most savage. It’s terrific writing, offering incredible insight into how Rebecca sees herself as a romantic option for Josh while also instantly creating a rival we love to hate (and, eventually, just love).
https://www.youtube.com/watch?v=seEOEUmFAFI
8.) “Face Your Fears” (from Episode 1.3, “I Hope Josh Comes to My Party”)
Any Crazy Ex-Girlfriend fan is already well aware that Donna Lynne Champlin is an Emmy worthy powerhouse who frequently stole the show with her powerful vocals. There honestly could have been a whole different list devoted to ranking her ten best solos. But praising her incredible voice feels redundant. “Face Your Fears” highlights something different: her ability to be funny through song. Every single line of this song is hilarious, largely because of her delivery and body language. Whether she’s leading a children’s choir in a dangerous sing-a-long, or encouraging Rebecca to do something brave like, “Join the Marines!,” she makes it work. And also worth noting: the “Face Your Fears” reprise, seen later in Season 3, is one of the most emotional moments in the series and absolutely played a part in earning this song a slot on the list.
https://www.youtube.com/watch?v=DrytvZc5Tew
7.) “Strip Away My Conscience” (from Episode 3.2, “To Josh, With Love.”)
It’s wild that it took Crazy Ex-Girlfriend three seasons to get to a Fosse number, but it was well worth the wait. “Strip Away My Conscience” is a total blast, with some of the series’ most impressive choreography and an unusually edgy set of lyrics. But, seeing as this is Crazy Ex-Girlfriend, the song also serves as a deconstruction of those Fosse-type musical numbers, rolling its eyes at anyone who uses sexiness from movies and television to inform their real-world attractions. It’s simple, clever, and a lot of fun, while also remaining one of their most quotable numbers, right down to a line about choking on “cock-suredeness” that still feels like it cheated the censors.
6.) “Remember That We Suffer” (from Episode 2.10, “Will Scarsdale Like Josh’s Shayna Punim?”)
One of Crazy Ex-Girlfriend‘s hidden talents is its ability to take a full thesis paper and condense it into a two-and-a-half minute song. “Remember That We Suffer” is probably the best example of this strength. While staying very funny, it thoroughly explores the way that older generations in our families can delegitimize our cries for help, using the problems they’ve faced or broader issues throughout history as excuses to fully ignore your own. Crazy Ex-Girlfriend never offers answers about how to deal with this generational gap, but by acknowledging it the series added a whole layer to much of its ensemble, making Rebecca’s mental health struggles all the more realized, while providing depth to her comically flawed mother. Plus, Patti LuPone sings a verse. What’s not to love?
https://www.youtube.com/watch?v=chyUpmnKimU
5.) “Let’s Generalize About Men” (from Episode 3.1, “Josh’s Ex-Girlfriend Wants Revenge”)
One of the very best things about Crazy Ex-Girlfriend is that it often feels totally relatable, and that might not be more apparent than during the climatic musical number in season three’s premiere, “Let’s Generalize About Men.” This 80s pop-rock song, accompanied with terrific production design and costumes, feels like the perfect theme song for any friend group comprised of people who enjoy dating men, but also frequently loathe them. It’s clever, silly, and goes off on a hilarious, winking tangent about how “gay men are all really great.” If there was any justice in the world, this number would have gone viral and made the show a cultural phenomenon, even if only for one brief moment.
4.) “A Diagnosis” (from Episode 3.6, “Josh Is Irrelevant.”)
The first half of Crazy Ex-Girlfriend‘s third season was a troubling batch of episodes, as the series got dark in a way that felt truly shocking and ultimately culminated in a disturbing suicide attempt from our protagonist. But that’s what made the following episode so cathartic: Rebecca survived and, for the first time in the series, started treatment for her mental health. As such, “A Diagnosis” is one of the series’ most emotional numbers, and feels like a fitting conclusion to the first half of the series. This musical number changed Rebecca’s life and, in many ways, alters the series, beginning a second act that’s focused on recovery.
https://www.youtube.com/watch?v=nK2DlLmVc20
3.) “We Tapped That Ass” (from Episode 2.4, “When Will Josh and His Friend Leave Me Alone?”)
Never underestimate the power of a simple sex pun, especially when paired with two very talented dancers. “We Tapped That Ass” is as immature as it sounds, fueled by a never ending parade of double entendres about all the sex Rebecca had around her house with Josh and Greg. But these jokes all land, especially as the song progresses to lyrics that are quite edgy, making you wonder how they ever got them past the CW’s censors. And, of course, there is the magical singing and dancing abilities of Santino Fontana and Vincent Rodriguez, each scoring the biggest laughs they’d get through the whole series.
https://www.youtube.com/watch?v=ilztSh5Cr2E
2.) “Settle for Me” (from Episode 1.4, “I’m Going on a Date with Josh’s Friend”)
“Settle for Me” was the moment I fell in love with Crazy Ex-Girlfriend. It’s a funny song, but there’s something deeply bittersweet about it, as Greg propositions Rebecca while doing absolutely nothing to hide the intense baggage he’d bring into the relationship, namely his crippling self-hate. For all the humor on display, it’s incredibly, which basically summarizes what make Crazy Ex-Girlfriend special in three minutes. And the song has grown even more interesting over the four season run, as we’ve charted Greg’s growth as a character, revealing just how perceptive the show’s insights into self-doubt and relationships can be. And, of course, Santino Fontana has one of the smoothest voices in theater, making his biting sarcasm strangely seductive and charming.
https://www.youtube.com/watch?v=jtb-ZPOkMyI
1.) “The Math of Love Triangles” (from Episode 2.3, “All Signs Point to Josh… Or Is It Josh’s Friend?”)
By the time it aired “The Math of Love Triangles,” Crazy Ex-Girlfriend had many great musical numbers. But this one instantly felt like something different. Not only was it a spot-on spoof of Marilyn Monroe’s “Diamonds Are a Girl’s Best Friend,” highlighting the show’s ability to jump into every single genre of music and make it work. It also had some of the show’s funniest lyrics. But some of the lines are so piercing and dark, delivered with a wink that tries to make the audience miss just how sad and ominous this song really is. This was the beginning of a new act for Crazy Ex-Girlfriend, indicating that the charming rom-com was about to go to a dark place and, now that the show is wrapping up in a more positive place, it reveals just how brilliantly they charted out this whole series. Calling it the show’s peak suggests that the show failed to return to this level of quality, which is not true. But this song exemplifies everything wonderful about this series, and is the first number that pops into my head whenever I think about the show.
https://www.youtube.com/watch?v=epuILDZ3KIo
The finale of Crazy Ex-Girlfriend airs tonight on The CW.
