Photo-Illustration: Maya Robinson/Vulture

For two seasons, the CW’s Crazy Ex-Girlfriend has found wonderful ways to subvert rom-com tropes in favor of more daring, genre-bending, and just plain funny depictions of modern romance. Telling the seemingly wacky narrative of a lawyer who makes a cross-country move from New York to West Covina, California, to win back an old boyfriend after a chance street encounter, let’s just say, well, the situation’s a lot more nuanced than that.

“Ninety-eight percent of the songs we do are comedic,” the show’s star and co-creator Rachel Bloom tells Vulture. “My background of doing sketch comedy reflects that, because I approach the songs like sketch-comedy songs. Whatever the pattern of the funny you’re playing in the song is, it should be like fighting that genre. It should be an ‘opposite’ or something that doesn’t quite fit. Automatically, we’re always looking for ways to subvert tropes in songs.” Crazy’s co-creator, Aline Brosh McKenna, wholeheartedly agrees: “In the writers room, we’re steeped in it in both ways — what it’s like to do a rom-com conventionally, but then also we spend time deconstructing it.”

Ahead of Crazy Ex-Girlfriend’s second-season finale, Vulture spoke with Bloom and Brosh-McKenna about nine songs performed on the show — almost all of them romantically inclined — and the stories behind each one.

“Love Kernels”

“Even before Lemonade came out, we realized what we hadn’t really done was follow the trend of music videos these days, which are often short films. These dreamy, trippy short films. Part of the challenge in doing that, especially when you’re doing a comedy song, is that you want a very specific template in mind. With all of these modern songs, they’re all doing their own thing. Same with the music videos. The only way to parody that or pastiche it is to pastiche the very idea of the artsy piece itself. Aline and I had both been reading this book called Unrequited, by Lisa Phillips, which is a wonderful read about unrequited love. It’s this idea of what unrequited love feels like, which is kind of like these literal love kernels; these kernels of appreciation you get that help you hang onto your obsession. That seemed like a really interesting song idea, but we had to add a comedic take to it. So the take was to get overly metaphorical with it, and have it be super-dreamy and super-trippy in this self-indulgent way.” —Rachel Bloom

“The Math of Love Triangles”

“Like the way you write musical theater, we thought about what emotions Rebecca was feeling at that point in the show. She was in the middle of an actual love triangle, so we wanted to fit in this self-indulgent, conflicted emotion. And as someone who had been in a love triangle many, many years ago, there is a selfish oh, little ol’ me feeling that I wanted to capture. So what’s the comedic version of that? Oh, Marilyn Monroe, definitely. It seemed like the natural song for a love triangle. The interesting thing about writing that song was you could almost see it being a Marilyn Monroe song, like, trying to figure out the actual math of it all. There’s something very cutesy about that premise. The way to elevate it from being cute and clever to being funny and making fun of a genre is to completely ignore math and have the guys try to teach her math.” —RB

“It Was a Shit Show”

“That was a huge challenge from a storytelling perspective because it’s a good-bye to a very, very important character on the show. One that was very important for Rebecca and the show and for us. If you’re looking for one song in the entire season that we spent the most time talking about, it’s this one. There were a lot of discussions and the songwriters went down a number of different paths, and then we would come together and talk about it frequently. During the first month of writing, there were a lot of versions of Rachel and Adam [Schlesinger] and Jack [Dolgen] popping in and out and trying different versions of a good-bye song. It was hard because they did have a love story that was unconventional, and he doesn’t say, ‘I love you,’ until the minute he’s leaving her. This is, when you think about it, the scene where he finally says, ‘I love you,’ after really missing his chance. So the question was how to find the song that really conveyed all that love that he had for Rebecca, his good-bye, and the ‘I need to not be around you’ factor.

The team probably wrote 15 or 16 versions of different types of songs. I remember Rachel came to me and said, I don’t know how to write this song without swearing. It’s just a song that calls for swearing, Aline! We had a thing last year where we tried to do some bleeps for a certain song, but the network said no, so we couldn’t have them last year. They said we could perhaps have them next season if we had a pressing need, but that’s the only time we’ll ever let you do it. We had these bleeps on hold in our bank account! So we went to the network again and asked for the bleeps for ‘Shit Show.’ We asked for three, and got two.” —Aline Brosh McKenna

“We Tapped That Ass”

“What happens is Greg leaves and there was a strong sense that there needed to be a continuation of the divine and the continuation of him haunting her. Rachel had this brilliant idea of the two of them coming back to haunt her. The tapping came about because Vincent and Santino are both tappers. Vinny is a very, very dedicated tapper and that’s also Santino’s strength as a dancer. It started out as a ghost-haunting song and as soon as somebody said the words ‘tap that ass,’ it came together. You know, sometimes these songs are birthed in a very laborious fashion. Sometimes the baby is breaching backwards. ‘Shit Show’ is a good example of that, where it takes a million tries to even come up with the idea; we’re switching genres, we’re having numerous conversations, and we’re running back and forth in the office. But not with this one! As soon as the idea of ‘tap that ass’ came, it was just a question of executing it and making it not too dirty for television.” —ABM

“Research Me Obsessively”

“Isn’t Brittany Snow the best? We were talking about wanting her to have some sort of song that Rebecca and Valencia see in their heads. In a way, that’s the spiritual sequel to the second episode in the first season: ‘Josh’s Girlfriend Is Really Cool!’ It’s Rebecca and Valencia developing an obsession with Anna in the same way that Rebecca became obsessed with Valencia. Like ‘I’m So Good at Yoga,’ we wanted them to have a fantasy sequence that lead into their obsession. There were a lot a ways to go about doing it, but at the end of the day, we were like, What about a seduction song? That’s really what that song is. In their heads, they’re being seduced into being obsessed with this girl. One of the templates was ‘Good for You,’ by Selena Gomez; she said the word ‘good’ really weird in that song. This kind of seductive, young girl, slow pop song. Originally, the song was called ‘Stalk Me,’ actually. But Aline brought up a good point and was like, I’d rather not write a song for a young lady who’s fairly famous on our show called ‘Stalk Me.’ We were like, wow that’s completely fair. So we changed the title, which I think is also great, and doesn’t encourage people to stalk Brittany Snow.” —RB

“Friendtopia”

“We were thinking about what the epitome of girl power and girl-power pop is, and the Spice Girls literally coined the term ‘girl power.’ Every other song from the Spice Girls is legitimately like, These are me and my friends, nothing is ever going to come between me and my friends, don’t come between me and my friends! I just really wanted to do a Spice Girls number. Leaning into this idea of the group having very distinct personalities was very fun. In the writers room, we were talking about songs like ‘Spice Up Your Life’ that paints this picture of we’re taking over the world with our friendship and love. So, what was the flip side? We were like, okay, nobody is going to come between you and your friends. Who is actually going to come between you? Why are you so obsessed with this idea of ‘don’t come between me and my friends?’ There’s this offensiveness to those songs that’s really funny. I really love dystopian topics in general, so the idea of taking it to the fifth degree, where they want to create a 1984-like world where the only thing that matters is their friendship, was appealing.” —RB

“Remember That We Suffered”

“We knew we were going to do a back-to-Scarsdale episode. Originally, it was going to be a wedding. We were thinking it was going to be Audra Levine’s wedding, but then because we had our own wedding stuff coming up we decided to simplify it a bit by making it a bar mitzvah. My son just had his bar mitzvah, so that was a very ripe opportunity still fresh in my mind. Rachel and Jack and Rachel’s husband Dan Gregor had previously done an album of Chanukah songs, and one of the songs was called ‘Think About All the Dead Jews,’ which is quite funny and thematically linked to this in the reasoning that Jews can’t get away from injecting misery into happy occasions. This is a slightly less offensive way of conveying that. So that’s another song that came rather quickly. As soon as the trio had the idea, they stepped out, came back into the writers room, and sang it to us. It was a really fast turnaround.” —ABM

“Santa Ana Winds”

“That one was a really difficult story to crack, writing-wise, because we wanted to do this idea of ‘you having a sex dream of someone you work with and then it’s super uncomfortable.’ Then it expanded out to everyone having weird dreams that aren’t all necessarily sex dreams. We separately had this idea of a very specific California thing, which is the Santa Ana winds and how they make people behave. We spent a ton of time mapping out the story and we definitely wanted to do Frankie Valli–style of music; it’s something we had been talking about for a long time. We were writing the story and putting an outline up, and talking about the Frankie Valli and the Four Seasons sound, and Rachel got very giddy and started walking around the room going, weeeeeeeee. Even when we were writing the episode, every once in awhile she would break into the weeeeeeeee.

Finding a seamless way to integrate it into the story was challenging, because we don’t normally do things like that and the Santa Ana winds guy isn’t a regular character. One thing that’s funny is that he was originally just scheduled to appear as the Santa Ana winds guy, but it was super-confusing, so we cut his first appearance and added the idea that he’s a weatherman. That’s how it gets into her mind. So we added that little blip of him being the weatherman wearing that suit and moving in a certain way, and that was a last-minute story addition to justify the song. You can see that the guy got imprinted in Rebecca’s head.” —ABM

“Period Sex”

“‘Period Sex’ was a song I really went to battle for all season. I was like, We are making this happen! By the time we teased it in the third episode, we knew it was going to be a full song at some point. I got in a booth with Adam and we collaborated on it. He put the ‘Period Sex’ vamp on loop and it was a combination of making shit up, going into the writers room for a few minutes, coming up with some more jokes, and editing it from there. The bridge was completely improvised and Adam created music around it. It’s weird because in some ways that song can’t be taken out of context — as a song itself, it’s silly, but I think the best context is to understand, This is what Rebecca wanted to sing all season? The song is kind of disgusting but also really empowering.” —RB