“It’s a lot more nuanced than that.” – The Top 20 Crazy Ex-Girlfriend Musical Numbers

Posted by Kim and Sage

On April 5, Crazy Ex-Girlfriend comes to an end on its own terms, after a well-plotted four-season run that expanded our idea of what TV – and TV musicals – are capable of. Never has there been a comedic heroine quite like co-creator Rachel Bloom’s Rebecca Bunch – brilliant, social, mentally ill, and romantic, full of big dreams and bad ideas. Her stumbles have been hard to watch sometimes, but the show has always bravely gone there, whilst building up a troupe of supporting and side characters that we’ll also be sad to see go.

I hope that we’ll see more fearless female creators stepping up as Rachel and Aline Brosh McKenna wrap up this story, because the end of Crazy Ex-Girlfriend is going to leave a huge hole on TV when it comes to honest, messy depictions of sex, relationships, mental health, toxic (and non-toxic) masculinity, and even capitalism. Original songs have been its vehicle for doing that, so, yes, here’s yet another list of the best numbers in CXG history. The difference between ours and all the others is that we’re right. –Sage

20) “The First Penis I Saw” (3 x 07)

Kim: Honestly, I can’t believe that it took Crazy Ex-Girlfriend two and a half seasons to finally do an ABBA number. But then again, I think they were savvy enough to hold this one until the buzz for Mamma Mia 2 was building and the nostalgia for the first movie was at an all time high. “The First Penis I Saw” is everything an ABBA homage should be: joyous, a little silly, and catchy as hell. And I still can’t believe they got away with Paula singing into an eggplant.

Sage: A trip to Paula’s hometown and an old boyfriend sighting yields this ABBA-inspired grocery store number about about some formative moments in her life. As ever, Donna Lynne Champlin sells this one like the show is going out of business, her carnal nostalgic glee is as catchy as the song itself.

19) “Don’t Be A Lawyer” (4 x 03)

Sage: Put Bobby Brown and New Edition in general on notice. I love a CXG number that lets one of the show’s stupidly talented recurring cast members step into the spotlight, and this final season finally gave Jim his moment. Who knew Burl Moseley was a New Jack Swing BEAST?

Kim: THESE LYRICS THOUGH. Clever, truth-dropping lyrics have always been a signature of CXG‘s musical numbers, but “Don’t Be A Lawyer” really takes it to another level. I honestly want to play this song for anyone that tells me I should think about going to law school. Sing with me now! “No money! No, no money!”

18) “You’re My Best Friend (And I Know I’m Not Yours)” (2 x 11)

Kim: First things first, I loved that flamingo sweater of Paula’s SO MUCH I tweeted the costume designer, and when she replied saying it was from New York and Company, I promptly went on Poshmark and found IT MY SIZE for ten bucks. And that’s the story of how I cosplay Paula every time we go to a CXG related event. ANYWAY.

Darryl Whitefeather is overbearing, over-enthusiastic, and a bit too willing to overshare. And you know what else he is? He’s the friend that will stop on their way to work to get you breakfast cause you always run late and forget to eat. He’s the friend that you call at 3 AM when you need someone to rescue you. He’s the friend who will pull an all-nighter with you before a big exam. No questions asked. He’s the purest, sweetest soul and we should all be so lucky to have a friend like him.

Sage: Crazy Ex-Girlfriend understands the power that musicals have to illustrate a feeling that’s otherwise impossible to communicate, and that’s what this sweet little song of Darryl’s does. His love for Paula is so pure. It doesn’t demand anything. And it’s just another example of why Mr. Whitefeather is such a special, necessary character. As Pete Gardner said about him in The New York Times the other day, “You can’t love people too much. You can’t love too hard. It doesn’t cost you anything. It really doesn’t. You can just love people and support them and send positive waves their way. And it just makes their life better. It makes your life better.” That’s not always easy to do, but Darryl makes it look a lot more accessible.

17) “I’m So Good At Yoga” (1 x 02)

Sage: The evolution of Valencia and Rebecca’s relationship is very close to my heart, but I’ll always miss that bitchy, possessive version of the former, just a little bit. “I’m So Good At Yoga” is a lyrical masterpiece that should always be watched/listened to in its explicit form (“Anal doesn’t hurt at all, sometimes I prefer it. That’s what this tattoo says.”), and it’s one of the show’s most impressive dance numbers too. (Yep, that’s Alex fucking Wong back there.)

Kim: I agree with Sage. While I love and am so happy with Valencia’s character arc, she was such a good villain in season one. Gabrielle Ruiz is gorgeous to begin with, so already she’s intimidating, but what made Valencia so deliciously evil was her attitude. It was the way she carried herself with confidence that bordered on arrogance. And yes, it was in the way she was so good at yoga. No wonder, Rebecca both cowered in her presence and fell a little bit in love with her all at the same time.

16) “I Could If I Wanted To” (1 x 16)

Kim: We have never hidden the fact that we are staunchly Team Greg here at Head Over Feels. If we TRULY let our biases show and made this about favorites, every single one of Greg’s solo songs would be on this list. (Yes, the amount of Greg you see on this list is us restraining ourselves.) When it comes down to it though, Sage and I decided that “I Could If I Wanted To” is Greg’s signature song. It encapsulates everything we love (and everything that makes us nuts) about Greg Serrano from the misanthropic attitude to the scowl to the gentleman protesting too much about NOT caring which means he DOES to the goddamn hoodie and tee combo. (And for me, this is the number where it clicked that Santino’s delivery rings REAL close to Joel McHale’s Jeff Winger, thus causing my head to explode.) Add that to the fact that Santino did this grunge rock number in one long continuous shot and you have the makings of a classic.

Sage: Oh, original Greg. Gregory Serrano. Love of my my damn LIFE.

His ’90s alt-rock solo explains SO MUCH about the most cynical bartender in West Covina, foreshadowing the moment where he decides that he actually DOES want to and WILL try, thank you very much. Santino Fontana’s phrasing and emphasis make this one work as well as it does, though, shout out as well to the man who gets visibly annoyed to be called out for his “big dad calves.”

15) “Ping Pong Girl” (2 x 02)

Sage: I love “Ping Pong Girl” so much that it was my Halloween costume one year. Very few people got it, but the ones who did were DELIGHTED. As annoyed as I frequently am with Josh Chan, I’m always charmed by Vinnie, who goes all in on this pop-punk parody about being the cool guy’s girl who’s effortlessly hot and hot because she’s effortless.

Kim: This is a BOP that would stand toe to toe with the greatest hits from Sum 41, Good Charlotte, and Blink 182. Thank you for your time.

14) “Fit Hot Guys Have Problems Too” (3 x 09)

Kim: I’ll never forget the first time I saw “Fit Hot Guys,” it changed me that much. I was on my couch with all of my girls, all of us clutching our wine in one hand and our metaphorical pearls with the other. 2018 had barely begun and it had already become one of the seminal television moments of the year. CXG is a deep show that has tackled a lot of issues over the course of its four seasons, but it is also a show that knows its audience. And sometimes, all we really want to see is hot men stripping off their clothes and dancing whilst singing about their feelings.

Sage: I read a lot about what the boys endured to prepare for this scene and I’d just like to thank them again for their service. We’d been begging for White Josh’s turn to sing for a couple of seasons by the time this happened, yet we never could have anticipated that “Fit Hot Guys” would be that moment. Despite the fact that most women I know love musicals, there aren’t many that cater to the female gaze. This unabashedly thirsty (and funny) number makes up for it. (If you don’t literally scream when they rip off their pants, please check your pulse.)

13) “Anti-Depressants Are So Not A Big Deal” (4 x 13)

Sage: Very often, Crazy Ex-Girlfriend is a primer of how not to behave. But this take on the much debated aesthetic of La La Land is the opposite. There’s nothing like a show-stopping jazz number to remind you to stop feeling needlessly guilty about it and just take your damn meds.

Kim: Like I just said, I think CXG‘s lasting legacy will be the way it strove to normalize conversations about mental illness and never being afraid to GO THERE with its story. Mental illness can be, at its core, a very isolating disease, one where you feel incredibly alone in your journey. What “Anti-Depressants Are So Not A Big Deal” does is tells you that you’re not alone. In fact, you’re in the majority. The fact that they tell you that while doing a big brassy freaking tap number makes it even better.

12) “It Was A Shit Show” (2 x 04)

Kim: Greg’s final episode aired while we were fully ensconced in a hotel in Long Island, attending a Doctor Who convention. I’ll never forget Sage foolishly getting on Twitter one night, and her hand suddenly going to her chest as she sucked in a deep breath. “It’s Greg, isn’t it?” I remember saying. Sage just tearfully nodded. So I knew what was coming when I finally settled down to watch this episode, but at the same time, I didn’t. I wasn’t expecting him to go out with a devastating homage to “My Way” and to be frank, I don’t think I ever quite recovered from it.

Sage: Truly, my heart broke when Greg made his surprise exit. But Santino went out (or so we thought – “We Tapped That Ass” barely missed this top 20) with a big, old-fashioned musical theater ballad about the beautiful trash dump that was Greg and Rebecca’s relationship. We should’ve known by the passion and conviction in his voice (that VOICE, oh my GOD) that all of it would be fixable (or at least forgivable) in the end.

11) “A Diagnosis” (3 x 06)

Sage: It’s so satisfying when Crazy Ex-Girlfriend allows itself to get brazenly optimistic, and that’s what happens after Rebecca hits rock bottom and lands in the hospital. Of course, it doesn’t solve all of her existing problems and it also creates some new ones, but the thought of a new explanation for why she feels the way she does gives her and everyone watching some hope. I’m still bitter that this song wasn’t even nominated for the Emmy.

Kim: This is the “I Want” song that ushers in the third act of Crazy Ex-Girlfriend. As Sage said, “A Diagnosis” is so fucking hopeful. And what’s brilliant about this song is that there are no frills. There’s no big dance number, nor are there the clever wink-wink, nudge-nudge kind of lyrics that have always been the show’s signature. They just let the song stand on its own and Rachel belts the shit out of it, in a simple pretty dress. It’s Rebecca Bunch, stripped down to her core, seeing some light after being in a very, very, very dark place. It’s not the end of her story, but it is a new beginning. And that’s beautiful.

10) “The Math Of Love Triangles” (2 x 03)

Sage: Honestly, just replace every one of Katherine McPhee’s weak attempts at channeling Marilyn in Smash with Rachel Bloom’s “sexy little baby” version. We’ll all be better off.

Kim: I just finished re-watching Smash over a 4 day binge, and I wholeheartedly agree with Sage’s assessment. And how great was it when they brought this number back in Season Four, with all of Rebecca’s boys starring in it?

9) “After Everything I’ve Done For You (That You Didn’t Ask For)” (1 x 18)

Sage: People, if I don’t see Donna Lynne headlining a Broadway show within six months of this show ending, I’m going to burn the entire theater district to the ground. Towards the end of Season 1, she went full Mama Rose on Rebecca, giving us THAT. BELT. The song itself became a recurring theme, which make sense, considering how often these people use each other as excuses for indulging their own worst impulses.

Kim: The best decision this show ever made was populating the cast with Broadway Babies who could really do justice to all of these songs and bring them to life. This is nothing short of magnificent.

8) “Friendtopia” (2 x 06)

Kim: Also known as the song we sing every time we initiate a new member into our coven.

On a serious note, as much has been made of Rebecca’s love life with the boys over the course of the show, the true love story of the show has been Rebecca and her girlfriends. No matter what happens in the finale, she’s always gonna have her girls watch Hocus Pocus with.

Sage: Never has this show birthed a theme more suited to its own full concept album than “Dystopian Spice Girls.” Who among us doesn’t just want to drink rose and watch the world burn?

7) “The Sexy Getting Ready Song” (1 x 01)

Sage: CXG came on strong out of the GATE with “Sexy Getting Ready Song,” previewing all the ways it would go on to deconstruct our concept of femininity. By the time Rebecca was crying in her Spanx, I was in.

It also features a fantastic cameo by the late Nipsey Hussle, as the guy who can’t complete his guest verse after he realizes the torture she’s gone through just to prepare for a date. (“I gotta go apologize to some bitches.”)

Bonus: “The Trent Is Getting Ready Song,” which never fails to reduce me to tears.

Kim: This song was instantly iconic and immediately defined what CXG was gonna be about: preaching the truth and destroying the patriarchy through song. Bye-bye skin!

6) “The End Of The Movie” (3 x 04)

Kim: Life doesn’t make narrative sense, nuh-uh. THIS SONG IS TOO REAL OKAY. What I love so much about this number is that it checks in with not only Rebecca, but all of our supporting characters and their respective sub-plots, except those are the plots of THEIR life movies, and guess what, they are all in shitty places. (To quote The Holiday, you should always be the leading lady of your own life!) It’s a genius choice to have Josh Groban sing this; the man not only has the voice of an angel, he’s hilarious. And so even though the end of this episode is a real punch in the stomach, you find yourself laughing anyway. That’s this show in a nutshell really.

Sage: If you’re gonna have Josh Groban on your show, this is how you use him. As melodramatic as it is, “End of the Movie” puts this dark, dark moment (after Rebecca sleeps with Greg’s DAD) into perspective, lightening the mood for the audience while simultaneously explaining why our heroine’s arc was never going to be a smooth curve upwards.

5) “Let’s Have Intercourse” (2 x 11)

Sage: IMO, Ed Sheeran’s smarmy lady-worship deserves to be skewered, and who could do that better than Scott Michael Foster? Even in our grief over Greg, Nathaniel won us over easily, his particular brand of sexy narcissism tapping into that vein of unhealthy attraction to a guy who’s just not that into you that runs through almost all of us, no matter how hard our attempts at self-preservation try to kill it.

Kim: I’m so used to watching the live version of this song that it’s almost disconcerting to hear the studio recording with all its effects. It’s such a pitch-perfect send-up of Ed Sheeran, that when I saw him in concert (twice), I found myself humming “Let’s Have Intercourse” the entire time he played “Thinking Out Loud.” THAT is how good this song is and Scott delivers it flawlessly.

4) “You Stupid Bitch” (1 x 11)

Kim: Well, if you’re going to go down a spiral of self-loathing, you might as well do it as a torch song belting Celine Dion-esque character, amirite? Listen. We’ve all been there, and this song works because we’ve all fallen down that rabbit hole of loathing and blame and self-hated because of stupid decisions we’ve made. “You Stupid Bitch” is (unfortunately) a universal kind of song for most women and while it’s hard to watch, it’s also oddly comforting to see it put into words? CXG never shied away from making Rebecca messy as hell and for that, I thank them.

Sage: If I were a musical theater actor, I would walk into every single audition with this song prepared.

It’s oddly comforting, how much I identify with this one. I have quietly whispered most of the lyrics to myself on many different occasions (except for maybe “poopy little slut,” that’s not really in my repertoire). Rebecca’s wallowing isn’t really all that helpful though, and and rarely do we see the dude characters (least of all Josh Chan) blaming themselves for their “dumb and stupid, simple, self-hating” actions. So much of what Rebecca goes through over the four years of this show is about being stuck in this cycle, and I can’t be the only one who feels seen.

3) “Settle For Me” (1 x 04)

Sage: The execution is so swoony-worthy that it’s easy to forget how un-romantic the premise of it is. The choreography is dreamy. So are the costumes. So’s Santino doing his best Fred Astaire. How Rebecca kept fighting her latent attraction to Greg after this, I’ll never understand.

Kim: AGREE. Truth be told, I don’t know how CXG expected anyone to want Rebecca to end up with Josh Chan after this number. I was already on board with Greg from the first episode, but I was a goner from the moment Greg said his heart went tippity-tap-tap. ALL I AM SAYING IS if they somehow bring this back in the finale, I will combust. (Even though Skylar Astin is #NotMyGreg, I can admit he’s doing his damn best. But Santino’s shadow just looms large.)

2) “Getting Bi” (1 x 14)

Kim: My favorite thing about Darryl’s coming out and everything that follows is that his bisexuality is never a punchline. (Which, even in the year of our Lord Two Thousand and Nineteen, bisexuality often still CAN be used as a punchline, or worse hinted at and then outright dismissed.) Sure, his coworkers are like OMG make him stop, but that’s because he’s oversharing and no one wants to hear that much about their boss’ sex life, not because he’s bisexual. And that? Well that’s just beautiful.

Sage: We need more joyful, uncomplicated coming out moments on TV, and if they each came with a sax-fueled track that would make Huey Lewis AND the News blush, even better.

1) “Let’s Generalize About Men” (3 x 01)

Sage: The crowning jewel of Crazy Ex-Girlfriend, “Let’s Generalize About Men” is the perfect marriage of satire, performer, costume, set design, lyrics, and concept, a rallying cry for all of us who just need to vent. We know it’s not ACTUALLY “all 3.6 billion men,” but it FEELS that way most of the time. No number on the show has spoken to me more (not even “You Stupid Bitch”!), and I’ve participated in too many boozy singalongs to not know that most of my friends get it too.

Kim: You get at least four of our group of girls together and this masterpiece gets played on YouTube. It’s the first thing we go to whenever we go down a Crazy Ex-Girlfriend video spree. “Let’s Generalize About Men” so perfectly captures the essence of girls’ night in. We put it on and we become every movie cliche of girls dancing around and singing into their hairbrushes. Singing along at the top of our lungs to this gem is nothing short of cathartic. (Plus, as a big boobed lady, I will never ever get over the way Rebecca is free boobing and just LETTING THEM FLIP AND FLOP AROUND as she rants. Mad respect.) My only question is…when is going to be added to the catalog at our local karaoke bar???

What’s YOUR favorite Crazy Ex-Girlfriend song? Let us know in the comments.