The 7 Best Songs of Crazy Ex-Girlfriend

After four fantastic seasons, Crazy Ex-Girlfriend is coming to an end. So I thought I’d take a look the best seven songs of the series — in chronological order, because don’t make me rank them.

(Except, of course, this list is not objective or exhaustive, the show is full of amazing songs, and if I wrote this list tomorrow, I’d probably include some different ones. But as the show wraps up, these are the ones that stick out to me!)

What’ll It Be (Hey West Covina) feat. Santino Fontana

Everyone’s going home, cos it’s time to give thanks

Thanks for the chain stores and outlets and banks

Thanks for this town three short hours from the beach

Where all of your dreams can stay just out of reach

What’ll It Be was sung by Greg in the show’s seventh episode, My First Thanksgiving With Josh!, and it’s the first time the show went straight for the emotional punch. The show’s comedy songs had had some more serious underlying subtext in the past — like Rebecca’s interrupted cry that she is NOT having a nervous breakdown in West Covina — but this play on songs like Piano Man is the first time the show went “yes, this song is funny, but also, enjoy that heartbreaking pathos, suckers.”

In What’ll It Be, Greg sits alone in the bar where he works on Thanksgiving, lamenting the fact that he feels utterly trapped in his life — West Covina has nothing to offer him, but he has had to abandon his dream of going to business school to care for his dad. Santino Fontana’s Broadway pipes and piano playing skills get a great showcase, as Greg pours his heart into this hopeless lament, despite never having played piano before. It definitely contrasts with this episode’s other song, the rap parody, I Give Good Parent.

I think — although I may be wrong on this — that this is the first time the show had a song that wasn’t imagined by Rebecca. Until this point, all musical interludes occur when she’s present, choreographed in her head. But she doesn’t know what Greg is up to here. He’s alone, and he’s depressed, suffering with alcoholism, although nobody realises it yet… and so he sings this song. It changes the whole tone of the show.

Which made it even better when the song got a reprise in the latest season, sung by a very different Greg, in more ways than one.

You Stupid Bitch feat. Rachel Bloom

You’re just a lying little bitch who ruins things

And wants the world to burn.


You’re a stupid bitch.

And lose some weight.

There’s an anecdote about this song, that Rachel Bloom was in the writers’ room, workshopping the lyrics, and someone told her… stop trying to fit in the jokes. You’ve earned the sincerity of this moment. Embrace it.

And so she does.

Rebecca sings You Stupid Bitch in Season One, Episode 11, That Text Was Not Meant for Josh!, after her latest card pyramid of lies collapses. Josh figures out that she staged the break-in of her own house and storms out, leaving her sitting on the floor of her living room, contemplating the shards of broken glass and hating every last inch of herself. The song plays off big sweeping Celine Dion-esque numbers, and it’s staged incredibly simply, as though Rebecca is a diva performing this classic on stage to an audience.

Thank you! Thank you, thank you! It’s so wonderful to be back here, even though I’m here singing this song a lot.

As the song continues, she spirals into her self loathing, getting more and more aggressive as she insults every aspect of herself. It’s a heartbreaking, and heartbreakingly relatable, song. This is the gut-punch that the show has been building up to all season. “You thought this was a farcical comedy, did you?” it laughs. “You thought you were having FUN? Well, here’s what’s actually going on. This woman is having a breakdown, and you were LAUGHING along, you monster.”

It Was a Shit Show feat. Santino Fontana

And when you say
That I should stay
That’s exactly when I should split, though
I won’t forget
I won’t regret
This beautiful, heart-stopping, breathtaking, life-changing–

This is Santino Fontana’s last song on the show, and boy is it a doozy. After a season and a half of heartbreak and drama, Greg is leaving West Covina to go to business school in Atlanta. He’s finally chasing his dream. But Rebecca runs after him in the airport, to beg him not to go. She loves him, and he loves her, and they can make it work.

But they can’t make it work. Greg and Rebecca bring out the worst in each other at this stage in their lives, and neither can get better with the other there. This play on songs like My Way is probably my most listened-to song from the whole show, despite not being very fun at all, because… god, it’s just heartbreaking, and Santino Fontana’s voice is like butter.

And the way it doesn’t finish the final line, how Greg nearly kisses her and then turns and walks away, with no resolution? Argh, my heart.

Strip Away My Conscience feat. Rachel Bloom

Lead me to the dark side
Like a lamb to the slaughter
Then do me in a hot tub filled with evil ‘stead of water
Let’s make war not love all night and day
It’s hot here in hell so…
Strip it all away

OK, enough heartbreaking songs. This song isn’t on my list of bests because it’s a massive game changer in the series. It’s just a play on Chicago with some awesome singing from Rachel Bloom and a Harry Potter reference, and it ends up on my playlist a lot.

This song appears in Season 3 Episode 2, To Josh With Love. Rebecca is determined to get her revenge on Josh for leaving her at the altar, so she goes to Nathaniel, the most sexy-evil person she knows, for help. And she imagines a whole musical seduction sequence, even though… well, it really wasn’t necessary, considering how much Nathaniel is into her.

The End of the Movie feat. Josh Groban

If you saw a movie that was like real life
You’d be like, “What the hell was that movie about?
It was really all over the place.”
Life doesn’t make narrative sense.

Aaaand back to the heartbreak! It’s a few episodes later in Season 3, and all of Rebecca’s plans have crashed back down on her. Everyone has learned about her past of mental illness thanks to Josh’s intervention. When her friends try to help her, she attacks them and storms out, and the rest of the episode is just one big spiral, as she imagines herself as the femme fatale in a thriller, but really just careens towards rock bottom.

So then we have this song, sung by Josh Groban as Rebecca walks through the empty streets. The first time I heard it, I didn’t like it so much as some of the show’s previous gut punch songs, but the more I listened to it, the more I appreciated how clever the music is. And it hurts. It hurts so much. This is the lowest Rebecca can go, the challenge to the show’s central conceit, that she imagines herself as a heroine in a musical. And god, my heart.

A Diagnosis feat. Rachel Bloom

I’m aware mental illness is stigmatized
But the stigma is worth it if I’ve realized
Who I’m meant to be, armed with my diagnosis.

God, the hope in this song. After Rebecca tries to kill herself and asks for help, she’s referred to a new therapist, who says he has a new diagnosis for her mental illness. After years of struggling, Rebecca imagines how this diagnosis might finally make her life make sense and give her a sense of belonging. She belts her heart out in her cheery yellow dress, and it’s so heartbreakingly hopeful, because you know that although a diagnosis is a powerful thing, Rebecca is putting too much faith in this turning point in her imagined story again. And yet it’s so relatable. This is the first episode where the show addresses Rebecca’s mental illness explicitly, putting a name to the difficulties she’s struggled with since the very first episode, and this song perfectly captures one of the ups on the rollercoaster towards recovery.

Face Your Fears (Reprise) feat. Rachel Bloom

I’ve never been afraid of opening my heart

For the slightest chance at love, I’d gladly tear my life apart

But now I finally have a sense of who I am inside

So do I risk it all again, or do I run and hide?

I’m a sucker for a reprise, and this one just punched me straight in the gut. Rebecca has been receiving treatment for her Borderline Personality Disorder, and she has made a lot of progress, but things with Nathaniel are still a mess. But she gathers her courage and goes to his apartment to tell him how she really feels. As she stands outside his door, she reprises Paula’s song from Season One, replacing that version’s jokey, overblown tone with genuine struggle. She attempts to steel herself with the song, telling herself to face her fears. The song seems to lead up to a big moment of resolve, when she’ll be brave and honest, but as she gets to the second to last time, she wavers. “Love is not as scary as it appears,” she sings, fear in her eyes, “All I gotta do is face my–” Then she stops, unable to finish the song. The light around her changes, from musical fantasy to reality. She begins to panic. And when Nathaniel opens the door, she is gone.

Special Mention: I Go To The Zoo feat. Scott Michael Foster

I go to the zoo in San Diego

It’s really such a better zoo

I could pretend there is some deeper meaning to this song, or say something about how this is the first time we see Nathanial’s softer side, but… nope. I just think this Lonely Island parody is really funny and catchy, and listened to it and sung it a lot. Now, a couple of years later, I still just need to say the words “it’s like a zoo for fishies” to drive my friends insane.

Thanks, Crazy Ex-Girlfriend, for all your hilarity and heartbreak. I’ll miss ya!

What do you think?

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