'Crazy Ex-Girlfriend' Star Rachel Bloom Breaks Down Four Standout Songs From New Season 2 Soundtrack

Smallz & Raskind/The CW
 Rachel Bloom as Rebecca Bunch in Crazy Ex-Girlfriend

A lot of ground was covered over the last 13 episodes of The CW's musical rom-com series Crazy Ex-Girlfriend -- from Rebecca's on-and-off relationship with summer-camp soul mate Josh Chan to the departure of lovable loser Greg and the arrival of hostile-but-hot new boss Nathaniel -- and all those transitions are represented (in song!) on the show's just-released season 2 soundtrack.

The crew behind Crazy Ex-Girlfriend -- including creator and star Rachel Bloom and executive music producer Adam Schlesinger, also of Fountains of Wayne fame -- have compiled 34 songs from season 2 for the soundtrack (out on iTunes now) as well as five bonus tracks that show how Bloom's rough demos become the show's polished musical numbers.

"We could have filled an album out with just demo tracks, frankly," Bloom tells Billboard. "Every song has multiple demo tracks of me singing into my iPhone and then the demo singer doing the full track or Adam doing the full track. And so it was just a matter of picking some cut songs that we're definitely not going to reuse and then also showing what the process is. I mean, one of the demos is me singing into my phone at 6 a.m. -- clearly my voice is shredded and I'm exhausted, but I wanted people to hear it so they'd understand what our process is and that it really is a 24/7 job for everyone working on this show."

Clearly the 24/7 work has paid off: Despite struggling in the ratings, the fan-favorite series has already been picked up for a season 3 -- so the song-and-dance continues. "We are in the middle of outlining the season right now," Bloom says of her work with fellow executive producer Aline Brosh McKenna. "We actually have more time this hiatus to write, just the two of us, because we had less episodes, so we ended sooner. It all feels a little bit more settled. So we're working on the general arc of the season right now."

Below, Bloom breaks down the process behind four of season 2's standout songs:

"Let's Have Intercourse"
We knew we wanted to have an unsentimental seduction song. And the joke of it being it would be a romantic seduction song, but the lyrics themselves would be very unromantic. So I think it was originally "Let's Get It Over With." I mean, had we not been censored, it would have been like "Let's Just F--- Already." So then you're looking for, what's the genre that can track with that the most? And there are many ways to do that. There's Michael Bublé, but we did a lot of that kind of crooner style with the character of Greg [Santino Fontana], and we wanted kind of another genre vocabulary. And we were watching Ed Sheeran's song ["Thinking Out Loud"], and it is so obviously sincere and the video is just so sincere and kind of saccharine, and he also does relatively little in the video; the girl is kind of doing the dancing, and he's just standing there -- it's pretty funny -- and so we went with that style, because if we have this kind of beautiful, sweeping sound, then we can have [Nathaniel, played by Scott Michael Foster] say the most dickish things. When you're writing these comedy songs, often the comedy comes from the contrast of what you're saying versus what the genre is.

"The Math of Love Triangles"
So we were thinking of what songs to have in episode 3, and I was kind of mulling it over and I was like, "OK, so when you're in a love triangle" -- I was in a love triangle in college and it ended very badly, but before it ended very badly, there was a feeling of self-indulgent woe, like, "Oh, what am I going to do? Two men love me? Oh no!" You know? And just the natural feeling of that is Marilyn Monroe, right? [In her Marilyn voice] "What's a girl to do?" And so I knew I wanted to call it "The Math of Love Triangles," and so I started at work just writing out all these math puns, and then I got home and I got into the bath -- I write a lot in the bath. It's probably how I'm going to die. I'm going to get electrocuted someday because I have my computer on a bath caddy, and yeah, it's literally how I'm going to die, but it's worth it because I write great things in the bath, so it's fine. So I'm writing in the tub, and I'm writing all of these math puns, you know "[I'll be swinging from a] hypote-noose," and I'm chuckling to myself, but then what I realized is, "Oh, you know, this is coming off as an actually kind of sincere Marilyn Monroe song, so what's a further, edgy comedy take so that it doesn't just sound like a cute musical theater song?" And the edgy comedy take is the men actually trying to legitimately teach her math and breaking the rhyme scheme. So I sent that pretty fully formed to Adam, and then he did a couple of melody tweaks and then just produced the track beautifully. "Man math" was the lyrical contribution of [writer and music consultant] Jack [Dolgen], and that's one of my favorite lyrics -- so thank you, Jack! But I am personally, as a writer and a performer -- just because that was one of the songs from the season that I was one of the main writers of -- I'm very proud of that song. I'm really proud of it.

"Remember That We Suffered"
We knew this was going to be a bar mitzvah thing, and a couple years ago, I did an album of all Hanukkah comedy songs with Jack and my husband, Dan Gregor, who also co-wrote the episode that this song was in ["Will Scarsdale Like Josh's Shayna Punim?"], and there was a song on that album called "Think About All the Dead Jews," which is a take on a hora, and we were like, "Oh, maybe we could repurpose a version of that song or use elements of that song for the show." They'll never let us say "Think About All the Dead Jews," but also that song was always kind of half-formed. It's like we almost had it, we were like 95 percent there, so we took the core of that song and did some heavy rewrites, and then Adam actually did a rewrite on the melody. By the time we took it from the album, it was a totally new song -- and better, I think, a better version of the original. And it was just such a fun song to do. And [guest stars] Patti [LuPone] and Tovah [Feldshuh] just knock it out of the park.

"Who's the New Guy?"
That is the song I'm really proud of, because we'd never done a Whitefeather workplace ensemble song, and I was listening to songs from How to Succeed in Business Without Really Trying, and I was just listening to general workplace musical theater songs, and oh my God, we had so many versions of that song. There was one that was called "Whistle Through the Fear," where everyone just sang, "Don't panic, just whistle through the fear," which is kind of "Whistle While You Work" meets "I Whistle a Happy Tune," and they all felt a little soft. Then I remember I was literally walking from my office back to set to film and I was brainstorming with Jack, and I was like, "What we really need is a song that voices what the audience is thinking, which is like, 'Who's the new guy? What the f--- is happening?'" And I was like, "Oh my God, what if that's the song?" It's a meta-song, but the characters don't realize they're being meta. The characters have no idea they're in a TV show, so everything is justified with them. I'm really proud of the line we cross in that, and it was kind of a "How much do we want to project that he's a potential love interest in the song?" We ended up not doing it, but there was definitely a version of a line where it was like, "Oh, we clearly see where this is going." You know, he's really attractive. We didn't end up doing this, but there was one time there was going to be a lyric of like, "I really miss Greg -- you know, the janitor Greg." And then we were like, eh, I don't want to project that he's going to be a love interest by saying I miss Greg. And so that was a really fun song to write.