Over the course of four seasons, the CW’s musical comedy Crazy Ex-Girlfriendproduced more than 150 original songs. Created by Rachel Bloom and Aline Brosh McKenna,the showfollowed the delightfully alarming journey of Rebecca Bunch (Bloom), a high-powered New York attorney. After a chance encounter with her teen camp boyfriend Josh (Vincent Rodriguez III), she blows up her life to follow him to West Covina, California (just three short hours from the beach). As she schemes to get with Josh — and later to get revenge on Josh — she makes, loses, and reconnects with new friends, tangles herself up in romantic knots, and finds a way toward a happier and healthier version of herself.
All this was accomplished through the power, and often delirious absurdity, of song. Spanning big Broadway belters, pop parodies, and genre jokes, the show’s original songs (by the team of Bloom, Jack Dolgen, and the late Adam Schlesinger) operated as both vehicles for hilarious and frequently audacious jokes and as windows into the darkest parts of their characters’ psyches. And often, they somehow managed to do both at once.
With so many songs to choose from, picking favorites is an enormously individual exercise. Forget the Myers-Briggs or the star signs — personalities can be organized around whether a song like “I Gave You a UTI” cracks your top ten. While we wait for Bloom and McKenna’s latest collaboration — a new comedy in development for Hulu, Badass (and Her Sister) — here are the 13 best songs from their first project together. Your list, though, may absolutely vary.
RELATED: Top 10 'Crazy Ex-Girlfriend' Songs Not Sung by the Show's Main Cast
"The Math of Love Triangles,” Season 2
This pitch-perfect Marilyn Monroe parody finds a breathy “sexy little baby”-voiced Rebecca surrounded by a chorus of dapper mathematicians. While they try desperately to teach her about triangles, she can only see herself in the center — or in all four of a triangle’s centers, as the boys helpfully point out. It’s one of the purest examples of the show’s songs operating on all possible levels: spot-on parody and performance, laugh-out-loud jokes, character exploration, and hints at the darker forces driving the cheerful tone. A fourth season reprise proves that this number has legs (as the chorus would say, that’s also a triangle pun).
"Face Your Fears,” Season 1
This early number was the first time audiences got a taste of just what Broadway veteran Donna Lynne Champlin was capable of. Playing Paula, Rebecca’s coworker, new friend, and enthusiastic co-conspirator in the pursuit of Josh, Champlin lets her full vocal power loose on this gospel-tinged number full of inspirational platitudes about courage and extremely bad advice. The jokes and the vocal runs are both impeccable, leaving just enough space for Paula’s budding codependence to peek through. “School is stupid,” according to the sweet children’s backing chorus, but this song is anything but.
"Anti-Depressants Are So Not a Big Deal,” Season 4
As the show spiraled out from its initial premise, the deconstruction of rom-com clichés gave way to a sincere (and also hilarious) exploration of mental health. This La La Land-inspired group number, fronted by Rebecca’s long-suffering therapist Dr. Akopian (Michael Hyatt), is a technicolored and tap-danced celebration of how common — and therefore how un-shameful — it is to seek pharmaceutical help for mental illness. All of Hyatt’s numbers are treats, but this one makes the list for its precise parody, its frank approach to mental health struggles, and the crucial impact it has on Rebecca’s journey toward accepting the help she needs. It’s just so hard to resist a song that assures, with a grin and a timestep, that “when it comes to meds, you’re such a basic bitch.”
"Gettin' Bi,” Season 1
Through much of the first season, Rebecca’s boss Darryl (Pete Gardner) had certain defining characteristics: He was sweet, a bit clingy, gloriously mustachioed, and loved his daughter (but not in a creepy way — see the honorable mentions below). But with his budding attraction to White Josh (David Hull), Darryl discovered alongside the audience that he was “a bi kinda guy. There's no reason to be shy.” Darryl embraces this midlife discovery, coming out to his disinterested coworkers with a Huey Lewis-inspired extravaganza of horns, keytars, and popped collars. It’s an exuberant celebration, a methodical rebuke of stereotypes, and catchy as all get out.
"You Go First,” Season 2
This teased-and-mulleted, bombastic tribute to '80s female power duos was one of the surprisingly rare chances Rebecca and Paula got to sing together. They make the most of it — both Bloom and Champlin let loose, singing their Hearts out (pun absolutely intended) as they mourn and blame each other for the fractures in their relationship. The vocals and the hair soar, leaving room for a sharp exploration of female friendship, guilt, and passive aggression: “Go ahead and say you’re kind of sorry,” they belt, “so I can say ‘oh no no no please,’ just like I rehearsed.” For all the show's romcom trappings, this relationship was its emotional center, and it earns every one of this number’s synthesizer-supported high notes.
"It Was A S*** Show,” Season 2
Sending off Santino Fontana’s Greg in the second season with an appropriately memorable song was never going to be easy. This “My Way” parody more than meets the moment. Its sweeping melody showcases the eventual Tony winner’s rich range, and that gorgeous performance helps the jokes sing. “We can't undo, can't make amends / Dysfunction is our lingua franca,” Greg sings soulfully in farewell to a tearful Rebecca. “We can't unscrew each other’s friends. / We're Jerry Springer, not Casablanca.” But despite the frank assessment of their disastrous time together, Fontana still manages to sweep us away with the final, bittersweet crescendo. In Fontana’s hands, the ballad is a beautiful tribute to the “play about pieces of feces” that was Greg and Rebecca’s early relationship.
"No One Else Is Singing My Song,” Season 4
Nathaniel (Scott Michael Foster) is on a wilderness retreat, Josh is alone at the bar, Rebecca is in prison, and they’re all feeling lonely. Insistent that they are each the only person who could possibly feel this particular way, they begin a group number that starts as a trio before expanding to “11-part harmony” about the absolutely singular, not-at-all-shared experience of feeling alone. Through an increasingly specific series of metaphors and music-theory jokes that link them together, 10 of the singers discover their connection, leaning into one of the show’s core beliefs: No one is as unique in their struggles as they feel. “Reach out [your] lonely hand” and you’ll likely find someone who knows how you feel.
"Let's Have Intercourse,” Season 2
The addition of Foster’s Nathaniel in Season 2 was a gamble, addressed in-show with the supporting cast’s “Who’s the New Guy?” But he quickly earned his place in an enemies-to-lovers plotline with Rebecca, and the turn was kicked off with this delicious and terrible come-on song. Stuck in an elevator together, Nathaniel offers one way to pass the time in an Ed Sheeran-like croon: “Unfortunately I want to have sex with you,” he offers. “Let’s get this over with so I can focus on other tasks” might not be the sexiest pick-up line, but it does make this delightfully mean pop ballad one of the show’s most hysterical songs and cements Nathaniel’s spot in Rebecca’s trio of love-ish interests.
"Let's Generalize About Men,” Season 3
This rosé-fueled, Pointer Sisters-inspired pop gem features the show’s four main women (Bloom, Champlin, Vella Lovell, and Gabrielle Ruiz) in all their 80s glory. As they rail against “all 3.6 billion men” (well, the straight ones, anyway) for their stereotypical grunts, inhibitions, and predilection for wings, the lyrics spiral out into ever funnier extremes. The broader the generalizations, the more riotous the song, until every man is painted as a dangerous criminal — including Paula’s own sons, because rules are rules. “Let's take one bad thing about one man, / And apply it to all of them,” the woman sing in unison over an inescapably catchy tune, offering and then undercutting an empowerment anthem for the “righteously mad.”
"A Diagnosis,” Season 3
Having reached her mental health low, “A Diagnosis” finds Rebecca peeking into the light. Modeled on a mid-tempo, major-key inspirational belter, “A Diagnosis” is special for just how straightforwardly it plays its hand. There are a few jokes about the conditions Rebecca might find herself facing, but for the most part, it’s a simple celebration of the possibility of finally finding herself. After two and a half seasons of watching her deny and run from her mental health struggles, it’s moving to see her so fully embrace the possibility of healing (even if she’s hopeful that it’ll be “an easy fix”). “The stigma is worth it if I've realized who I'm meant to be, armed with my diagnosis,” Rebecca sings with the passion usually reserved for romantic revelations. It’s the show’s turning point on the journey toward Rebecca’s ultimate revelation: her most important relationship is the one she builds with herself.
"Don't Be a Lawyer,” Season 4
Four seasons in, Crazy Ex-Girlfriend managed to deliver one of its very funniest numbers and showcase a long-time supporting player all at once. Burl Moseley’s Jim was a familiar face, first as one of the lawyer’s in Rebecca’s firm and then as the proprietor of the building’s pretzel shop. In this gloriously neon, Bobby Brown-influenced plea to avoid the bar, he gets his major musical showcase, featuring energetic choreography, terrific vocals, and some of the show’s most quotable lyrics. “There are so many other professions that don’t turn you into Jeff Sessions,” Jim reminds anyone considering law. Jim himself may not ultimately follow his own advice, but with a song this dazzlingly catchy, audiences won’t forget it.
"The Miracle of Birth,” Season 3
One of the show’s most notable characteristics was the frankness with which it treated the female body and all its usually unspeakable… quirks. In this gentle, folksy number, Paula assures Heather (Vella Lovell) that her impending childbirth will be miraculous and absolutely horrifying. All loose waves, lilting tones, and gentle smiles, Paula goes into excruciating detail about each step of labor and delivery from atop a throne, under which precious ballerinas enter through a pair of pink curtains. It’s a real “how did they get away with this?” moment, delivered with one of Champlin’s prettiest vocals. Try your very best not to find yourself singing “And oops! There it went-a! That was the placenta / Which you must expel, or you will surely die” the next time you chat with a pregnant person.
"You Stupid Bitch,” Season 1
Though favorite songs from this show vary widely, it’s almost unimaginable that this song, perhaps the show’s signature number, wouldn’t be included on any list. At her lowest point of the first season, Rebecca imagines herself in a sequined gown, singing her biggest hit to a crowd ready to scream the lyrics back at her: “You ruined everything, you stupid stupid bitch,” she belts in this Barbra Streisand-inflected ballad. It’s the show at its double-duty best: The juxtaposition of the lush orchestrations and soaring vocals against the vitriolic lyrics is very funny. But there’s an honesty in the spangly self-loathing, laying bare her struggles and calling to mind our own darkest moments.
Honorable Mentions
For all its smart deconstruction and character building, the show could also turn out gleefully silly and quotable songs for the fun of it. Favorites include Nathaniel’s “I Go to the Zoo” (best line: "I go to the aquarium. It’s like a zoo for fishies.”); Rebecca’s “A Buttload of Cats” (the chorus of cats’ best line: “Yes we saw that article in The Atlantic. And then we peed on The Atlantic.”); and Darryl’s “I Love My Daughter (But Not In a Creepy Way)” (best line: “Having a daughter is WEEEIIIIIRD”).
