In honor of songwriter Adam Schlesinger, who passed away from COVID-19 complications this week, Vulture is celebrating his work across the entertainment industry, including his role as one of the masterminds of Crazy Ex-Girlfriend’s many original songs. This interview with Schlesinger originally ran in 2019, following the Crazy Ex-Girlfriend series finale.

Crazy Ex-Girlfriendwas one of the most formally daring shows in recent TV memory. Originally structured as a romantic comedy, the series played with the expectations of that genre, exploring mental illness, sexuality, and the instability of desire, romance, and professional success — the kinds of things characters on TV shows usually want. But more than any of its themes, the most thrilling part of Crazy Ex-Girlfriend was its music: Characters frequently expressed their feelings in song, riding a comic line between fantastic projection and broader musical “reality.”

After four seasons, 60 episodes, and more than 120 songs, Crazy Ex-Girlfriend assembled a remarkable body of original music, in pastiches of everything ranging from Cole Porter song-and-dance numbers to the Beach Boys. Now that it’s all over, Vulture asked the Crazy Ex-Girlfriend songwriting team — executive music producer Adam Schlesinger, writer Jack Dolgen, and star and series creator Rachel Bloom — to walk us through the nine most difficult songs from the show’s run.

“What’ll It Be” (Season 1, Episode 6)

Adam Schlesinger:Rachel had a general idea about doing a song for Greg that would be somewhat inspired sonically by “Piano Man,” but it was supposed to be a sincere song, not a parody. It’s tough to write songs for the show that are more sincere and not just obvious jokes. You’re really trying to say something heartfelt from the character’s perspective, but still also make you smile a little bit.

Rachel Bloom:When you’re have a song that’s just filled with jokes, it’s borderline mathematical — this is inarguably the joke, this is how we hype the joke. But when you start to get more emotional, it can get artistically messy. What are we trying to say? Is this funny enough? Is it too funny? I still think “What’ll It Be” is one of my favorite songs the show has ever done. The song is all Adam. It was originally called “This Town Is Gonna Swallow Me Whole,” and I sent him a rough demo that was more of a “Piano Man” parody. He busted out “What’ll It Be,” and it was like, “Well, this is perfect.” Out of every song we’ve done, I’m shocked this hasn’t gotten radio play on its own. I know that’s naïve, but it’s just such a good song.

Adam Schlesinger:Early on in the show, I was staying in an Airbnb that had this cool piano. I had nothing to do that weekend, so I just sat there, working on the song. I first came up with the hook being “What’ll It Be,” because he was a bartender and it seemed like it had a nice double meaning to it. I started with that “Piano Man” musical vibe, and then let it take me somewhere else.

Rachel Bloom:I think Adam and Jack both really connected with Greg. There is something about how we all dial in to songs that come from characters we relate to. It takes it out of that comedy sketch world, and more into the feel of that scary gut emotional place.

Adam Schlesinger:Why do we both connect with the bitter asshole guy, Jack?

“It Was a Shit Show” (Season 2, Episode 4)

Rachel Bloom:We didn’t expect that [Santino Fontana] was leaving. Then we found out the day we got ordered to season two that he was not coming back. So you’re faced with a dilemma: How do you write someone out of the show and make it seem like it was always the plan? How do you earn it? We all come from a very improv mentality where there are no mistakes, so you pivot and go, “Okay, Greg is leaving. This was a choice in our improv game.” And you want to make the best show you can, so it’s like, “We’re not only going to make this seem like the best choice, we’re going to knock this out of the fucking park.”

When we were thinking about songs — what would be the best send-off for Greg, and what kind of thing hasn’t been done — and we kept thinking about Frank Sinatra’s “My Way.” Very torch song-y, very bombastic.We had all of the lyrics written in the verse, but we didn’t have a chorus. For most songs on the show, finding that hook line, finding the chorus, is the hardest thing. Once we find that hook, it’s not all downhill from there, but then there’s momentum.

It was such an emotional moment, the only thing that seemed right for the chorus was to say, “This was a fucking shit show.” [But] we were trying to write around not cursing. We could always put the dirty versions of songs on my YouTube channel, which we had done, especially in season one, but the song has to stand on its own clean, because that’s what’s airing on the CW and then later on Netflix. It’s not like we could do a song called “It Was a Shit Show” and then go back and say, like, “It Was a Bad Thing.” I remember just crying in my office. Adam and Jack were both there, probably not knowing where to look as I was crying.

Jack Dolgen: We were working under the constraint that we couldn’t bleep, so we wrote eight or ten versions of the song.

Rachel Bloom:We did. That’s when I cried, because “shit show” was the right way to do the song, but we couldn’t do it because they wouldn’t even give us bleeps. It wasn’t even an FCC thing — other shows bleep all the time, especially documentary-style shows like The Office and Parks and Rec. That was a CW call. So I begged. I said, “This is creatively necessary. It’s the riskiest thing we will ever have to do, and the only way to do it is if we curse. Otherwise, the song will fail and this will not work.” And they literally gave two shits. That’s partially why the song doesn’t end with [singing loud and dramatically] “shit shooooow!”

I’m always going to be proud of that song. I love what it says about relationships. I love what it says about their relationship — it sounded like Greg. It was a beautiful story song, and it was a lovely send-off to Greg part one. Me crying at the end of the scene is not acting. I’m crying at the loss of the character, and sadness and pain.

“Greg’s Drinking Song” (Season 2, Episode 2)

Jack Dolgen:When I did the first pass of this song, the entire chorus was “I shit my pants.” It was a very irreverent way of approaching the consequences of alcoholism from the perspective of someone who’s dealing with it. It was super fun and completely impossible to do on television, so we had to find ways of making it more usable. “I Pooped My Pants” is not enough to hang your hat for an entire song.

Rachel Bloom:Well, you quickly changed it to “I Crap My Pants,” which was funny! We thought we could use that, but that’s when we learned all about the ins and outs of standards and practices. You can say, “I don’t give a crap” or “Oh crap, I dropped that banana.” But you cannot use “crap” in referring to defecation.

Jack Dolgen:I forgot about that!

Rachel Bloom:“I Poop My Pants” or “I Pee My Pants” is fine, because, I don’t know, it’s not using a curse. What the CW said to us in our first meeting with them was, “Don’t hold yourselves back, we’ll pull you back. We’re going to help you navigate standards and practices.” And they completely followed through on that. People ask, “Would you rather have been on cable?” No, because those places didn’t understand what we were trying to do. FX turned down the pilot, like, “We thought it would be edgier.” The pilot featured a topless stripper in West Covina and me giving a hand job and then a blow job. Sure, we couldn’t curse, but I ultimately think we were with the network who understood what we were trying to do tonally. That meant way more to me than being able to say “fuck” or, like, show my asshole.

“We Tapped That Ass” (Season 2, Episode 2)

Adam Schlesinger:We knew that we wanted this to be a tap dance, but it wasn’t immediately apparent that the title was “We Tapped That Ass.” Jack threw that line out in the middle of the brainstorming session. It was a beat later that we were like, “Oh, duh, that’s the title.”

Rachel Bloom:I’ll remember that moment forever. The first idea I had was an old-school tap number, and it goes. “Fucked ya here, fucked ya there.” And then it was, “We banged ya here, banged ya there.” We needed something else to make it pop, so we were trading jokes and Jack goes, “What about the line, tapped that ass?” And it was like, “Fucking brilliant, motherfucker. That’s the song.” And it got us an Emmy nomination! So thanks, Jack.

Rachel Bloom:If I don’t get Alzheimer’s and my brain doesn’t rot, I’ll always remember that creative experience. It was just an unbelievable three brains merging.

Adam Schlesinger:Your other brilliant moment while we were working on that was “back pati-oooh!” We all just died.

Jack Dolgen: Who came up with “Where should we finish?” “How about on her chest?”

Rachel Bloom:We originally had the guys saying, “Where should we finish?” “How about on her chest?” And S&P said, “No way.” We put in the chest of drawers and it still wasn’t enough. So I got on the phone with S&P and said, “This is the greatest joke, how can we do this?” And they were like, “Well, if you were a little more descriptive about it being about the literal chest, and maybe if Rebecca said the line, so that it’s not two guys saying they’re going to finish on her chest.” So that’s why I go, “Please not on my chest.” That was how we sold it to S&P. And it felt like we gave up nothing. “Tap That Ass,” that’s our crowning achievement in not only getting past the censors, but in getting S&P to agree to some of this.

“Hello, Nice to Meet You” (Season 4, Episode 10)

Rachel Bloom:With “Hello, Nice to Meet You,” I had originally envisioned a kind of slow waltz, this very sweet song with Greg coming back that had an aching to it. From the second we knew we wanted Greg back, I started thinking about a song they could sing that covers the idea of meeting someone again for the first time.

I played the song for Aline, and she said, “Huh, this isn’t what I thought it would be.” It was a really hard day on set. The unspoken thing with a lot of this is, we don’t get to write and then film and then edit — we have to do all of them at once. I usually start to snap, mentally, around the middle of the season. So I go to set and burst into tears, just uncontrollably sobbing. Then I took her note in, and went, “How much do I agree with this?” And I do think she was right. You needed an upbeat song to cut through a potentially treacly moment that was earned later in that serious reprise in episode ten.

“The Darkness” (Season 4, Episode 12)

Rachel Bloom:That song is pretty autobiographical. Rebecca and I are different people — I don’t have BPD, but I have dealt with depression and anxiety. And sadness, which I think is pretty universal as a human. When I describe how anxiety feels to my psychiatrist, all I can say is, “It’s the darkness.” It feels like someone tapping on your shoulder, or like you’re wearing this heavy backpack and you can’t shake it off. So I wrote this song with the twist that the darkness is this lover. Not only that, we’re doing it in this Carpenters style, [so] how can we heighten further the idea that it’s this great innocent love?

There was some pushback among the three of us songwriters, but what the pushback taught me how to do was take a step back and look at the song and say, “How can I make the song better, but still keep emotionally what I loved?” Some of the best lyrics on that song came from addressing notes to which I was initially resistant — “We played solitaire in the shade,” “Tyler,” “He sleeps around and calls me a slut,” which later became “His pet name for me is slut.”

Jack Dolgen:When you’re watching it, you’re really getting straight to the core emotional expression. And the joke is peppered in there really nicely. It’s the kind of song that’s hard to pull off when you’re trying to carry really serious stuff, but with a comedic angle. Those songs are always challenging.

Rachel Bloom:There were a lot of permutations. We always knew we wanted to do some sort of Rebecca serious song, because it had been a while since we had a Rebecca solo song. Originally, we were going to write a Joni Mitchell song about being on a lazy river justifying why Raging Waters was so important to her. It was going to be a sort of free-floating Joni Mitchell song on a lazy river, and then we found out we couldn’t use the lazy river.

“The Miracle of Birth” (Season 3, Episode 13)

Jack Dolgen:This was a unique challenge to write because I never gave birth. But I was tasked with it because we were really time crunched. It came down to Adam and me finishing writing the song in like an hour.

Rachel Bloom:I was filming on set, so I couldn’t do anything. You guys were on your own.

Jack Dolgen:As a dude in a predominantly female writers room, I’d learned to keep my ears open and learn about shit I don’t know about. First, I went to all of the moms on the writing staff and asked them to tell me about their birth experiences. So it was me, the various moms, and our writers assistant at the time, Hailey, who has also never given birth. We were listening to the moms’ birthing stories and Hailey and I just sat there horrified. Hailey was like, “Well, I’m never doing that!” Everyone’s stories were just so graphic and so intense. It’s so fucking animal. And also unbelievably impressive.

I brought that to Adam and we tried to quickly write a song about it. When I ran the lyrics by the moms, we got big laughs and a thumbs-up votes of approval, which meant a lot to me, because we wanted to honor the actual experience of childbirth. We wouldn’t have been able to do that without their contributions.

Adam Schlesinger:The basic framework for the joke is that we made the song as beautiful sounding as we could, in contrast to the most disgusting lyrics that are all 100 percent real. Once we started going with it, we were just cracking up. Aline came in at one point and grossified — or clarified — some things even more.

Jack Dolgen:It was a really cool experience for me to write outside of your knowledge base, outside of your depth, and honor it. And that was often a challenge for me, writing a female lead. It actually made me a better writer and a better human being. “Miracle of Birth” was sort of a culmination of that process. Thank God I got to spend four years in that writers room and not, like, writing about some dude.

“Forget It” (Season 4, Episode 7)

Jack Dolgen:“Forget It” is a very rare situation. The three of us just jammed on it, and then it got removed from the episode, meaning we never shot it. It wasn’t going to fit the story, but then miraculously, we found an appropriate spot for it in a later episode. It needed a zhuzh lyrically, but coming back around to a song, I can’t remember if that happened again.

Rachel Bloom:It was originally slated for the episode where Rebecca tries to commit suicide at her mother’s house, but it didn’t add anything narratively to the episode because we knew Rebecca’s mom was going to be shitty. But the episode became more about the opposite — about the mother realizing [Rebecca] wanted to kill herself, seeming very nice, and drugging her — so when we came to the next Scarsdale episode, that song worked. Rebecca was in a moment where she actually had hope that her mother would be accepting of her lifestyle, because she had seen a low moment in her mother’s life, and thought maybe they could finally connect. I love that song so hard.

Adam Schlesinger:Me too. I remember having to convince Tovah [Feldshuh] that it wasn’t going to be too fast, that it was going to be okay.

Rachel Bloom:Tovah is a classically trained actress. She was trained by Uta Hagen, and is a theater actor with a capital T — I have a video of her practicing “Forget It” with a highlighter in her mouth, because that’s apparently a way you can warm up your consonants. Tovah was in the writers room and she was talking about her own mother saying, “What, you’re going to be an actress? You’re going to humiliate yourself? Forget it!” And that became her catchphrase.

Adam Schlesinger:It’s like the Jewish version of fuggedaboutit! “Where’s the Bathroom” was just right in her wheelhouse — she got it right away and killed it, and in fact ended up doing it in her own live shows later on, which is the ultimate compliment. With “Forget It,” she wasn’t familiar with the pop genre we were playing around with, but once she wrapped her mind around it and put her own stamp on it, she totally owned it.

Rachel Bloom:She asked, “How do you want me to move?” I said, “Tovah, it’s not ‘Where’s the Bathroom.’ Imagine you’re a 15-year-old, sexy, waiflike pop star and this entire video is shot with a creepy male gaze.” She really connected to that. I just kept saying, “Younger, younger! Picture the camera going over every inch of your body in this kind of voyeuristic gaze.”

“Getting Bi” (Season 1, Episode 14)

Adam Schlesinger:Rachel had the initial idea — that Darryl would have a song about coming out as bi and the joke is that no one gives a shit — and Rachel originally pitched it as being this kind of old-timey, 1920s-ish song.

Rachel Bloom:The original idea was a Rebecca Bunch–like manic statement of purpose called “By the By, I’m Bi.” But I prefer what it ended up being, which is an actual bi anthem that people use to come out to their families.

Adam Schlesinger:Left to our own devices, each of us have certain genres that we gravitate toward. Mine is usually some slightly dated pop or rock. And I just thought, “I feel like this character would definitely have Huey Lewis’s Sports.” That seemed like a genre in which he would be comfortable announcing his bisexuality.

Rachel Bloom:We made a version of the song and brought over a representative from GLAAD to help us with bi visibility. Like, “We’re making a bi anthem, let’s try to dispel some myths about bisexual people, especially bisexual men.” A lot of gay guys say, “Oh, there’s no such thing as a bisexual man.” So Adam put a lot of work in with, “Now some may say / Oh you’re just gay / Why don’t you go gay all the way?” It’s magical, especially when we do it live. You can see it in the concert special we’re airing. People stand up, they dance. It’s a fucking anthem.

Adam Schlesinger:Luckily, “bi” is a really easy word to rhyme.

The 9 Crazy Ex-Girlfriend Songs That Were Toughest to Write