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Rachel Bloom in "Crazy Ex-Girlfriend"
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JUST A GIRL IN LOVE

The 20 best songs from “Crazy Ex-Girlfriend,” ranked

Sam Rigby
By Sam Rigby

Growth editor

Crazy Ex-Girlfriend has never been the most popular show on television, but it has undoubtedly had some of the best, and weirdest, musical numbers.

Over four seasons, creators Rachel Bloom and Aline Brosh McKenna delivered a show that never shied from doing something different. It took a sexist trope, the “crazy ex-girlfriend,” and destroyed it, giving us one of TV’s most complex and loveable heroines in years.

And it pulled off the impressive feat of portraying mental illness—in particular borderline personality disorder—through musical-comedy. That could so easily have felt shallow and exploitative, but instead won praise and recognition from the mental health community, and was seen by many as a powerful and cathartic “mirror” to look into.

Of course, not all the extravagant, outrageous, belly-laugh-inducing original songs in Crazy Ex-Girlfriend—written by Bloom along with Jack Dolgen and Adam Schlesinger—had a higher social purpose. Most of the more than 150 song-and-dance numbers produced for the show were just plain entertaining. The show’s soundtrack has spanned genres, from homages to classic Busby Berkeley-style musicals to contemporary R&B, 1980s pop-rock, and Motown. The show’s lead choreographer, Kathryn Burns, won an Emmy for her extravagant productions, which sometimes featured the entire cast. And it’s a cast with some serious Broadway pedigree.

As the show builds towards its final ever episode on April 5, let’s go back and revisit some of our favorite musical moments:

20. “Anti-Depressants Are So Not A Big Deal” (season 4, episode 13)

“Fluoxetine, fluoxetine! Paroxetine, paroxetine! Citalopram, citalopram!” As far as hooks go, that has to rank as one of Crazy Ex-Girlfriend‘s best. Over four seasons, the series has sought to de-stigmatize mental illness, portraying Rebecca’s struggles with borderline personality disorder through a sensitive balance of drama and comedy. The show knows when to get serious about these issues, but it also knows how to have a hell of a lot of fun with them too, as this La La Land-inspired number proves.

19. “Let’s Have Intercourse” (season 2, episode 11)

As a love interest for Rebecca, Nathaniel never quite lived up to his early promise, but Rachel Bloom and Scott Michael Foster had real chemistry, and gave us some memorable songs along the way. “Let’s Have Intercourse” definitely goes down as one of the show’s funniest ballads, playing with Nathaniel’s obnoxious personality and reluctant attraction to Rebecca brilliantly.

18. “Maybe This Dream” (season 2, episode 2)

Ripped straight from a fairytale (albeit one that’s more PG-13 than G), Bloom has named this as one of her favorite songs from the show. “In college, Donna Lynne Champlin was told that the way she ‘looked’ didn’t match the fact she was a coloratura soprano,” she told The New York Times. The writing team proved them wrong, giving her this excellent princess song to showcase her skills.

17. “Where’s Rebecca Bunch?” (season 3, episode 1)

Plot-wise, Crazy Ex-Girlfriend has sometimes found itself weighed down by its wide cast of supporting characters, but there have been some occasions where that has worked to its advantage. Season three’s massive Disney musical-style opening brought the entire cast together to answer the questions left hanging from the previous season finale, and set up Rebecca’s plot for revenge against Josh.

16. “I Give Good Parent” (season 1, episode 6)

Crazy Ex-Girlfriend was originally destined for premium cable, but landed at the CW when Showtime decided to pass. The show underwent changes, most notably toning down its language for network TV. But that didn’t stop Bloom and the team pushing boundaries, and while “I Give Good Parent” was censored for broadcast, a look at Bloom’s YouTube channel gives you an insight into what we might have expected from a more R-rated series.

15. “The First Penis I Saw” (season 3, episode 7)

Bloom may be Crazy-Ex‘s big star, but the series would not have been the same without Donna Lynne Champlin as Rebecca’s bestie, Paula. “The First Penis I Saw” is Champlin at her most loveable. Penis puns, supermarket dancing, and ABBA influences = a Crazy Ex-Girlfriend classic.

14. “We Tapped That Ass” (season 2, episode 4)

When Rebecca’s imagination runs wild, we get the best musical numbers. As she struggled to deal with her feelings for both Josh and Greg in early season 2, she conjured up this vision of her two lovers teasing her about all the sex they had had around her house. It earned the show the second of its two Emmy nominations for Best Original Music, and with lyrics like these it really should have won.

13. “Sex With a Stranger” (season 1, episode 4)

To a generation whose sex and dating lives have been redefined by apps like Tinder and Grindr, this could well be the most relatable song on Crazy Ex-Girlfriend. “Hey, sexy stranger, come back to my place, and I hope you’re not a murderer,” captures that strange mix of lust and fear that comes with the modern hook-up. “Is that a gun? Oh thank god, it’s just your penis,” is a lyric for the ages.

12. “It Was a Shit Show” (season 2, episode 4)

Santino Fontana’s final song before Greg left West Covina (only to return in the final season, played by Skylar Astin) was the perfect curtain-closer on Rebecca and Greg’s sometimes brilliant, but often toxic relationship. Anyone who has been through a painful breakup can relate to this tribute to that special type of relationship that’s both “beautiful, heart-stopping, breathtaking, life-changing” and a total and utter shit show.

11. “Maybe She’s Not Such A Heinous Bitch After All” (season 3, episode 5)

Rebecca’s relationship with her judgmental mother is key to why she has struggled with her mental health for so long. The 1960s-tinged “Maybe She’s Not Such A Heinous Bitch After All” sees Rebecca reassess their relationship after some surprise mother-daughter bonding. It’s a moment of fun in an episode that traveled to some dark places.

10. “After Everything You Made Me Do (That You Didn’t Ask For)” (season 3, episode 2)

This was a moment. As Rebecca’s anger boiled over, she went to confront Josh for jilting her, and in the process managed to confess to every morally questionable thing she’d done over the course of two seasons. As Slate’s Marissa Martinelli wrote, “Rebecca’s ‘craziness’ is finally on full display, and while it’s cathartic in the moment, it’s definitely going to come back to haunt her.” And boy, it did.

9. “Oh My God I Think I Like You” (season 1, episode 17)

There’s a moment when uncomplicated sex becomes, well, complicated. “Oh My God I Think I Like You” sums up that dawning moment in all its confusing glory. It’s crude, but oddly sweet. A sentence that sums Crazy Ex-Girlfriend up pretty well, really.

8. “The Sexy Getting Ready Song” (season 1, episode 1)

When I discovered the series on Netflix, this was the song I’d play to all of my friends to convince them that they needed to get on board. A nod to all the “unsexy” things women do to look “sexy”, “The Sexy Getting Ready Song” was the first—and one of the best—parodies the show gave us.

7. “I’m Just a Girl In Love” (season 2 theme tune)

Each season, Crazy Ex-Girlfriend has changed up its theme tune… with mixed results. The first season’s was great, the third and fourth season’s less so. However, the award for Best Theme Tune has to go to season two’s “I’m Just a Girl In Love.” It’s cute and catchy, but it’s not as light-hearted as it appears. The season finale turned the song on its head as we realized just how these lyrics figured into Rebecca’s past.

6. “West Covina” (season 1, episode 1)

This is where it all began. Not in West Covina, California but in New York City as Rebecca Bunch ran away from her boring, corporate life in search of true love. This opener made you realize that this wasn’t going to be your average TV show, and it remains one of the best songs from the entire run.

5. “Love Kernels” (season 2, episode 1)

Who hasn’t felt like a sexy fashion cactus? Crazy Ex-Girlfriend kicked off its second season with this genius ode to unrequited love, satirizing the lengths to which we go to convince ourselves that the object of our affection feels the same way. It also happened to have a high-budget music video most pop stars would kill for.

4. “Let’s Generalize About Men” (season 3, episode 1)

“Right now, we’re angry and sad,” the show’s foursome of gal pals sing. “It’s our right to get righteously mad at every member of the opposite sex.” Some songs just arrive at exactly the right moment. There’s a lot to unpack in “Let’s Generalize About Men,” which offered the internet some light relief right at the peak of the #MeToo conversation. As an 1980s girl group, Rebecca, Paula, Valencia, and Heather get together to do what all girlfriends do—complain about how awful men are. But this isn’t just a song about men’s flaws, but society’s tendency to make sweeping generalizations because, ultimately, it makes us feel good.

3. “Settle For Me” (season 1, episode 4)

When Crazy Ex-Girlfriend was commissioned, Bloom was most excited about getting the chance to bring this song to life. Like “Love Kernels,” “Settle For Me” is about a particular kind of unrequited love, in this case the kind where you’d be more than happy to be a person’s Plan B. It remains to be seen whether Rebecca and Greg are endgame, but this was the moment we all found ourselves rooting for them.

2. “You Stupid Bitch” (season 1, episode 11)

Rebecca is a likeable character, but it’s not always been easy to feel like you should root for her. She makes mistakes, she tells lies, and people get hurt in the process. But in all of Crazy Ex-Girlfriend‘s madness, Rebecca’s journey of self-improvement and discovery has been the one that will stay with the audience longest. We’ve all done stupid things and we’ve all wanted to sing this song to ourselves. Rebecca, we relate.

1. “The Math of Love Triangles” (season 2, episode 3)

Picking just one song to top this list was not easy, but if one epitomizes the greatness of Crazy Ex-Girlfriend and the incredible talents of Rachel Bloom, it’s the hilarious, glorious “The Math of Love Triangles.” Channeling her best Marilyn Monroe, Rebecca muses on how difficult it is to be caught between two men. “The center of the triangle is lil’ ol’ me!” she coos. It’s true not just of this song, but of the show in general. Crazy Ex-Girlfriend has been a groundbreaking, if imperfect show, with the eccentric, loveable Rebecca Bunch at the center of it all. Crazy Ex-Girlfriend, I’ll miss you.

Honorable mentions: “I Have Friends,” “A Boy Band Made Up of Four Joshes,” “Research Me Obsessively,” “I’m A Good Person,” “We’ll Never Have Problems Again,” “A Diagnosis,” “I’m The Villain in My Own Story,” “Group Hang,” “Friendtopia,” “Gettin’ Bi,” “I’m In a Sexy French Depression,” “You Go First,” “Dream Ghost.” I could go on…

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