In Rachel Bloom’s animated music video “Historically Accurate Disney Princess Song,“ the princess in question wanders through her medieval town in search of love. Everyone seems to have found their prince but her, she laments in song, passing “the blacksmith with his daughter-wife, 10 years old and pregnant with her brother-son” and “a statue of Christ adorned with thief’s hands.” The princess dances and sings her way into the forest, where she encounters her friends, the Jews.“Hello, Jews!” she cries with delight, addressing a group of two-foot-tall rounded creatures with egg-heads, who don’t speak so much as chirp. One has a monocle in one eye and a diamond in his hand, while another has beady black eyes. A third wears glasses. They have big hook-noses and wear yarmulkes. “You know, I never did ask you: Why do you live in the forest?” the princess coos, in the tone every Disney princess takes with her little creaturely friends. The Jews answer her with their chirping. “Oh, I see,” she says, “to hide from people trying to kill you. Well, that’s very resourceful, my beaky little friends!” The princess drops gold coins on the floor as Cinderella dropped corn, and the Jews dutifully bend to nibble. “Tell me: Have you ever had a dream that wouldn’t come true?” she trills. “Oh, I see, your dream is that people won’t want to kill you. Well, that’s definitely a dream that won’t come true!” she says, as characters in armor start to shoot arrows at the Jews and chase them off screen. “Oh, goodbye, goodbye!” she calls. Then, scrunching up her little cartoon nose and slitting her eyes, she grunts: “Jews.”Like the best musical comedy videos of Weird Al and Saturday Night Live, “Historically Accurate Disney Princess Song” combines edgy comedy with great music. But Bloom’s trademark move is to take this combination one step further; rather than just a one-dimensional joke set to music, like “Dick in a Box” or “Amish Paradise,” Bloom transforms the musical comedy into social critique. “Historically Accurate Disney Princess Song” poses the dilemma, “Do you believe in true love and secretly wish you were a princess? Because that stuff’s all bound up with a whole bunch of other stuff you might not want to cop to.” In other words, the joke is on, but it is also on you.Rachel Bloom is about to go from video artist to household name. Showtime has just ordered a pilot for her comedy show Crazy Ex-Girlfriend, co-written with Aline Brosh McKenna of The Devil Wears Prada and to be directed by Marc Webb of Spiderman movie fame. The half-hour comedy (with musical elements) is about a girl who is successful but unhappy and who drops everything when she runs into her ex-boyfriend in order to stalk him and sing about it. “It’s about obsession,” Bloom explained when we met in March in Los Angeles. “When we’re obsessed with someone, it’s never about them. It’s about us hating ourselves. And that’s generally the tone of a lot of my videos, which is this desperate character who’s overcompensating with being super happy. But she’s broken.”***Bloom grew up in Manhattan Beach, outside Los Angeles. “Everyone around me was super-cool and laid back and skinny and tan and volleyball-y,” Bloom said, “and I was just this neurotic kid who was singing ‘Annie Get Your Gun.’ ” Bloom was bullied mercilessly throughout middle school. “I hadn’t embraced who I was yet. I was such a dork to the core—I was really in love with show tunes, and I had a weird fashion sense. I cut my own hair. I wish that I could have been, like, whatever, ‘Let my freak flag fly,’ but the thing is, I desperately wanted to be popular.”Despite—or perhaps because of—the ugliness of those memories, that time of her life still feels very real to her, informing more than one her music videos. In “I Steal Pets,” a 2011 video for collegehumor.com, Bloom plays a bullied high-school nerd who steals pets from the popular people, then dresses them up like the popular people and forces them to be her friends. “It’s very much an extrapolation of what I was,” Bloom says of the video. Dan Gregor, Bloom’s fiancé and sometime writing partner, sees “I Steal Pets” as a pivotal moment in Bloom’s emerging aesthetic, wherein she crystallized something in her comedic voice. “A slightly manic desperation to be loved, to be relevant, to be right—emotions we all have, but don’t often give voice too,” he explained in an email.Gregor, also a comedy writer, met Bloom when she became the director of the sketch comedy troupe he had started when he preceded her at New York University. When asked what it was like working with her, he answered, “Pretty great. I decided to marry her.” Bloom’s first request upon getting engaged was that the engagement party be dinosaur/space themed.Bloom’s ability to re-inhabit adolescence, especially its darker sides, led her to write one of her best songs, “You Can Touch My Boobies,” which won the 2013 LA Weekly Web Award for Best YouTube Song. The video is about a boy fantasizing about his Hebrew-school teacher: “Hey, Jeffrey Goldstein. Looks like you fell asleep in Hebrew school again. Well that’s OK. Cause now, you’re about to have a dream! And not just any dream … a sexy dream!” The chorus promises, “We’re gonna have some fun tonight/ ’Cause you can touch my boobies,” and there’s an interruption by Golda Meir: “Jeffrey! This is Golda Meir, the fourth prime minister of Israel! You’re disgusting! You are perverted! You have brought shame on your family and the Jewish people! You are going to be a rapist!” Bloom pays homage to the awkwardness but also the twisted creativity of adolescent sexuality. The song is also a sly ridiculing of how the typical pop song caters to male fantasies. “Those fantasies are for teenagers!” Bloom’s video argues. “Look!”“You Can Touch My Boobies” came to Bloom when she found some erotic poetry she had written when she was 11. “I was a very sexualized 11-year-old,” she said. “I remember the first crush I ever had starting at age 8, and it being as real and intense and passionate as any other crush I ever had, like, ‘I want this man inside me.’ And I think I started masturbating really young.” For years she wanted to do a sketch involving erotica as written by an 11-year-old. But then it occurred to her that a music video would be the perfect vehicle to show the deep gap between what pop culture says sexuality is and what it actually is. “Because sexuality isn’t just in the club. It’s like, you’re kind of most sexual when you’re, like 11, 12, 13, and it’s a really awkward sexuality.”Bloom’s most famous music video, “Fuck Me Ray Bradbury,” was featured in the Los Angeles Times and won the award for Best Music Video at the Dragon*Con convention. It was also nominated for a 2011 Hugo Award for Best Dramatic Presentation: Short Form. It’s about a maniacally cheery teenager who is erotically transfixed by Ray Bradbury, author of Fahrenheit 451, “the greatest sci-fi writer in history,” as the character sings.While writing and producing the video, Bloom was dogged by the imperative not to be cute. “I want hard jokes,” Bloom recalled. “I’m not just gonna be like, ‘Oh, Ray Bradbury, I give my heart to you,’ ” she said in a baby voice. “It’s like, ‘No, I wanna fuck you.’ ” The story revolves around a schoolgirl—played by Bloom—who declines a date with a cute boy so she can stay home and masturbate to Ray Bradbury’s books (“You write about Earthlings going to Mars/ And I write about blowing you in my car”). As in “You Can Touch My Boobies,” Bloom pays homage to the deeply sexual nature of youth. She is dressed like a schoolgirl (à la Britney Spears), but her unabashed horniness disables the male fantasy of stealing a Catholic schoolgirl’s purity. The video also satirizes the stereotypical male author who fantasizes about his female fans gushing about his genius; they are certainly not fantasizing about the protagonist Bloom plays.“Fuck Me Ray Bradbury” was released on Bradbury’s birthday. One of his friends sent Bloom a picture of him watching the video. “He looks kinda embarrassed,” Bloom said. “But I think he liked it.” But she couldn’t be sure; when Bloom finally met Bradbury, they spoke about his books and didn’t have time to talk about the video.***Bloom was raised with what she called a “heavy” Jewish identity. While the Blooms weren’t observant, her parents were “always going to Holocaust museums” and were “all up on who’s Jewish in Hollywood.” And it is this sensibility that is most ruthlessly and delightfully derided in Suck It, Christmas!!! (A Chanukah Album). The album—a joint endeavor of Bloom, Gregor, and Jack Dolgen, her producer—was released in November along with a music video of the second track, “Chanukah Honey” which parodies Eartha Kitt’s 1953 song “Santa Baby.” The video transforms Kitt’s bootie-call/ buy-me-stuff anthem into “a sexy holiday song about how Jewish girls hit on Jewish guys,” as Bloom put it. In her rendition, the sable and yacht of “Santa Baby” are replaced by an M.B.A. from Penn and playing basketball at the JCC: “So tall! You must be five-foot-eight!” Kitt’s innuendo is replaced by latke flipping, challah blessing, and mezuzah kissing.And where Kitt’s character is all coyness, Bloom’s character is demanding and aggressive, already piling on the chores she imagines her sweetheart will perform when they are married. In a move that characterizes Bloom’s comedic brilliance, the list of chores includes all the sexual favors that Kitt’s character was insinuating might be on offer for her paramour. The sexual promise of the 1950s coquette is the millennial Jewess’s demand. “So come kiss my mezuzah tonight,” Bloom sings—and then, in case you missed it, “Mezuzah is the name for my clit.”The rest of the album’s tracks are a mix of comedy sketches and musical numbers, a kind of Free To Be … You and Me with less Alan Alda and more Allan Sherman. The album has 11 tracks, including the rock operatic “Let Me Be the Cantor in Your Temple,” an electronic rap song about world travelers called “Judaica” (“In any city that I’m in/ I find the Holocaust Museum/ Watch Jacob the Liar on the telly/ And I’ll find the deli in New Delhi”), the ballad “Foreskin Angels,” and three tracks of the recovered minutes of the meetings of the Elders of Zion.“The guiding principle,” Gregor explained, via email, “was, ‘Will they enjoy this in a bunk of 13-year-olds at Jewish sleep-away camp?’ The brainstormings were basically three Jews reiterating the bitchings and observations of a lifetime of being involved in the Jewish community. When we felt like we were getting too dark, negative, or preachy, we’d ask ourselves if we thought Rachel’s cousin the rabbi would laugh at it or not.”“Rachel’s so sharp, and Gregor is such an incredible writer,” said Dolgen, the album’s producer, “that we just had so much fun, throwing ideas around and deciding how to tackle things. How much do we want to make fun of Jewish suffering and how it has shaped the modern Jewish identity? How far do we want to go in making fun of the Holocaust?“Not that we’re afraid of being inappropriate,” he added. “It’s really just, ‘Is it smart or not?’ That keeps everything in check. If it’s not smart, and it’s just vulgar for its own sake, that’s just boring and not that interesting, and hopefully we got over that in middle school. But if it’s smart, then you can get away with having a rapping aborted fetus.”Bloom has similar thoughts about the borderline between funny and offensive. “When the punchline is the Holocaust, when the punchline is, ‘black people are lazy,’ when the punch-line is, ‘wouldn’t it be funny if a woman got raped’—yes, it’s offensive. It’s narrow-minded. It’s narrow-minded comedically, it means the person isn’t that creative, it means the person has never tried to imagine themselves in another person’s shoes.” In other words, “Jokes that are gratuitously offensive are synonymous with bad writing to me. I’m offended as a writer first, and as a person second.”But Bloom also said that when people are finding their voice in comedy, “they say weird shit.” And, she added, what people find offensive is subjective. “One guy kept commenting on different videos from the Hanukkah album that, ‘This is offensive to Jews and Christians. Suck It, Christmas is an offensive title.’ That’s the point! What people are offended by is so nuanced, but ultimately stuff that is truly offensive is also just truly badly written.”Bloom’s work takes the sketch principle of heightening—elevating or adding information to a comedic idea—and adds to it an emotional aspect that is convincing and compelling and even surprisingly moving, while highlighting some very ridiculous aspects of being human. While her characters are obsessive and often crazed, there is something deeply affecting about their predicaments: the unpopular kid desperate enough for love to seek it from the pets of the popular people; the horny teenage girl refusing dates to make love to a favorite author’s work; the girl so lovelorn that she has no choice but to “post pictures of your tiny dick on the Internet.” Their pain is real, as real as the manic creativity that Bloom draws from their hysteria.