Rachel Bloom's first music video was called “F— Me, Ray Bradbury”; her second, “I Steal Pets.” Unorthodox, sure -- but the 29-year-old comedian has turned YouTube clicks into TV stardom with the Golden Globe-winning musical comedy Crazy Ex-Girlfriend, whose second season premieres Oct. 21 on the CW. “Just wait for the first episode,” she says coyly before sharing some of her most memorable music moments. “There’s a Beyoncé-style number that’s different -- and more expensive -- than anything we’ve ever done!”

What’s the first album you bought? How old were you?

The first album I bought was the soundtrack to the Goofy movie, which is a great soundtrack that holds up.

What was the first concert you attended? What do you remember from that experience?

True to form, the first concert I attended was Bette Midler’s at the Staples center. I remember especially when she entered, she rose up from a giant earth singing “From a Distance." Then I remember her singing a song about “sweet marijuana” called "Marihuana" that made me uncomfortable. Obviously not now, but at the time I was in sixth grade -- it was the first time I heard anyone talk about marijuana and I was with my parents.

What was the first slow dance song you danced to? Who did you go with? Were you nervous?

Probably at my 7th grade dance, which is when the dances started. I remember the first significant dance with my eighth grade boyfriend Willy. I don’t remember the song, but it was probably by *NSYNC.

I read that one of the first songs you learned was “All I Do Is Dream Of You” from Singin' in the Rain, then you became an outcast in school because it’s all you listened to. Why that song?

First of all, when you are an only child, you are a bit at the mercy of what your parents expose you to. My mother was a pianist and played a lot of show tunes, and grandfather, her father, who I spent a lot of time with, was an amateur standup comedian, theater director, singer and actor. He exposed me to Singin' in the Rain and taught me my first song. That’s why I gravitated toward that vocal sound, because my grandfather was in his mid seventies and he listened to music from the 30s, 40s and 50s. There was that. I didn’t get into the music Singin' in the Rain until later, I saw the movie first. I got into theater-based soundtracks, but that was definitely the foundation of my musical baseline.

What’s your favorite song to sing?

Well, I learned what gets me approval. Every time I would sing, I would hear applause. You don’t know anything about technique, but you know that people seemed impressed. It’s like learning any skill, and you learn when you are a kid, and the admiration of especially adults. But I loved singing show tunes.

What artist, album, song or concert made you want to get into music in popular culture?

I remember when I first heard The Offspring's Americana. It was the first non-musical show tunes thing I got into. I connected with them. There is something about them that feels musical theater just because there songs are these weird, wacky stories and they are very lyric focused. It’s the same reason that I gravitate sometimes toward rap and hip-hop. When you listen to a lot of musical theater you begin to tune out a lot of things where it’s not from a singer-songwriter aspect, where the instruments drown out the lyrics, and you gravitate toward things where you can hear the lyrics clearly. So that was a really important album. It was the first time I was listening to something other kids were listening to instead of forcing myself to like it.

What kind of rap and hip-hop are you into?

I’m really into Nicki Minaj. She’s just fantastic. And early 90s rap. I love that. I am by no means a connoisseur.

What singer do you think is the hardest to emulate vocally?

Well, a lot of singers are hard to emulate now because they are so Auto-Tuned. It’s hard to do an exact impression of them sometimes because by the time their track comes out, their voices don’t sound like voices anymore. I’ve tried to do a Katy Perry impression, but her vocal range is insane. Sometimes she’ll transition into places that are unexpected, like that breathy quality and head voice -- [starts singing “Teenage Dream”]. It just takes a while to understand what she is doing. It’s so unexpected.

First TV Theme song you couldn’t get out of your head?

The theme song to Hey Arnold. I love that song!

Are there any music genre’s you really want to explore on the next season of the show? Anything you can share before it comes out?

Basically every genre this season is new. I wanted to do a symbolic, beautiful Beyonce-type style number and that’s on the first episode. The Beyonce Lemonade song feels different from anything we have ever done. It feels like a beautiful short film, and the budget was big, and we hadn’t really done that before. We used a lot of our budget for episode one.

First song you listened to after winning a Golden Globe?

That whole night was a blur. I’m sure I listened to a lot music when I was out. So much was going on, I have no idea. There was so much music blasting at all these events. My problem if I’m going to listen to music, I want to actually listen to music. Just like if I want to dance, I want to dance. At events where dancing is not the primary activity and there is music playing, I have a real old lady problem with it. If it’s an event where you want to be talking to people and music is blasting, it’s like what are we doing? Tune the music down.

Favorite artist of all time?

Man, I mean if we are talking about singer-songwriters, I fucking love Ben Folds. I love how his songs sound. They are so lyric-focused and they are so beautiful. There are so many intangible beautiful things about how he writes music. They are also funny and they have a real point of view and they are very personal to him. I think with the specificity becomes more reliability. Even "Brick," it’s a really great song and it’s not a song that takes political sides, it’s just a song that happened to him. One of my favorite songs is “Belinda” -- it’s off the album he wrote with Nick Hornby, it’s so great and it’s so good and tells such a folk story. And Barbra Streisand has such a sweeping, emotive voice and it’s so unique -- when she gets to the top and it gets this chained wailing, it makes it sound so effortless and very specific to her.

First time a song made you laugh?

Weird Al’s “Fat” or “Eat It” -- toss up between those two. I saw him at the Hollywood Bowl a couple months ago and he did this parody of "Royals" with aluminum foil and it was fucking great. My husband and I had tears rolling down our cheeks.

What song would you use to describe the presidential election right now?

Umm.. wow. “Psycho Killer” by the Talking Heads. It’s both in how I think people feel and also about one of the candidates. I think for a long time I was a liberal without knowing too many specifics. I like watching the debate and then immediately going on PolitiFact and seeing what is true and what is false. I really think the debate should be annotated because Trump has this way of speaking very simply and very succinctly and he sounds like he knows what he’s talking about, and then you look up things and you realize he’s straight up lying. They both have this inability to answer the questions. Especially as a writer or comedian, I believe in being straightforward and no bullshit, and it’s just amazing they don’t answer a goddamn question. And the shit she had to put up with in the lifetime of being married, but you know, it’s very frustrating to watch.

First song you had sex to?

I really remember having sex in college and the show Futurama was on in the background. So I definitely had sex inadvertently to the theme song of the show.

First song you listened to while smoking pot?

[Laughs] Hmmmm…. one of the first times I smoked pot was the most cliché thing ever. I watched Wizard of Oz with Dark Side of the Moon playing. I know it’s the most cliché college experience but I always remember that. I just remember when the bike bell dinged and the music came on and it was like “woahhhhh!” It was when Miss Gulch's bike fell, that’s what I remember the most.

What song would you want to be playing on your deathbed or at your funeral?

I love that question. I’m so glad you asked me this. “Always Look on the Bright Side of Life” by Monty Python. I would like it because it’s a true, unsentimental look at life that still is beautiful and makes me want to cry. I fear death immensely. I think every second we are not fearing death we are trying to blissfully distract ourselves. I almost drowned when I was five. I remember the feeling of drowning and then my dad jumped in the pool and got me out. That was pretty scary and the closest I’ve come.

What was the first music video you couldn’t stop watching and why?

Hmmmm…. Um, God. I have to think about this. My friend showed me this video by this woman named Julie Brown, she’s a musical comedian in the 80s and it’s a song called "'Cause I’m a Blonde” and I love it a lot. I think it was the first time I had seen a woman doing comedic music videos. Before that I had seen all men, just Lonely Island and Weird Al and the South Park guys.

A version of this article originally appeared in the Oct. 29 issue of Billboard.