Late-night-television tapings attract a certain type of crowd: tourists in the mood for an uncomplicated thrill after a day at Universal Studios and Madame Tussauds. On a rainy January night in Los Angeles, the turnout at “Jimmy Kimmel Live!” was no exception. The overlap between the audience and the fan base for the musical guest — the Internet, a six-piece band of black alt-kids playing retro-futuristic R.&B. — seemed to be vanishingly narrow. If anything, the crowd looked as if they’d be right at home seeing Jimmy Buffett. But as the Internet cannonballed into its first song, “Get Away,” a thumping anthem about mollifying an unhappy girlfriend, the audience members threw up their hands and bounced along to the beat.  The women in attendance seemed especially mesmerized by Sydney Bennett — better known as Syd tha Kyd — the frontwoman, whose Tiger Beat sex appeal gave her performance a depth charge. Bennett, 23, brown-skinned with a blond-tinged Mohawk, has the swayback stance of an adolescent skater and dresses like one too: On the “Kimmel” set, she wore black vans, a black T-shirt and black jeans low on her hips. As she sang, she roamed across each quadrant of the small stage, staring deep into the throng, as if to find out whether her crush had bothered to make an appearance at the show. To create her stage presence, Bennett studied the R.&B. singer D’Angelo, whose 2000 video for “Untitled (How Does It Feel)” features nothing but his extremely defined and extremely nude upper body dripping with sweat for four and a half minutes. It showed. Bennett flirted with the crowd, peeking at them through her heavily lashed eyes, shooting sly smiles at fans and gently lifting her chin to acknowledge those she knew — among them, her mom, Janel, and her godmother, Sheryl.  The TV appearance was a rarity for the members of the Internet, who, as their name suggests, live online and work from home. Two of the band’s three albums were created and recorded almost entirely at the house where Bennett lives with her parents in L.A.’s Mid-City neighborhood. But their most recent record, last year’s “Ego Death,” caught the attention of the National Academy of Recording Arts and Sciences, and it was nominated for a Grammy in the Best Urban Contemporary Album category. (Past nominees in the category include Frank Ocean, Rihanna and Beyoncé.) The “Kimmel” performance was a dip into mainstream media that the Internet has largely succeeded without.  The band’s name itself hints at an irreversible and inevitable shift in the way music works. For decades, the music industry fancied itself an apparatus for tastemaking, but as technology has made labels’ role less relevant, that has ceased to be the case. Listeners decide what’s popular now, and record labels have to find a way to attach themselves to it. Aside from a few big-name acts, most artists are doomed to languish in relative obscurity with middling profits. This is usually seen as a tragedy — the death of a musical middle class — but it has also presented an opportunity for artists to avoid the suffocating effects of the label machine. And so the Internet has carved out an entirely new corner of R.&B., thanks mostly to Bennett: an androgyne who sings seductive incantations about falling in and out of love with women.  After the performance, a small constellation of cousins, little sisters and girlfriends milled about, snacking on doughnuts in the greenroom and helping the band pack up. After the equipment was loaded into a caravan of modest sedans and S.U.V.s, the band stood in a circle behind the studio, and someone produced a celebratory blunt. As the smoke drifted overhead, the conversation turned to the next day.  The group needed to practice for the first stop on their upcoming tour, which would start a few days later in Japan. Jameel Bruner, who plays the keyboard, wouldn’t be able to come until he was done with his shift at Amoeba Music, where he works as a clerk. There was drama to discuss, too. The 17-year-old guitar player, Steve Lacy, had been photographed smoking weed, and someone had texted the picture to his mother, who was not happy. Despite the chilly El Niño air, the band lingered, seeming reluctant to leave and break the spell of the evening. They eventually agreed to regroup at their home base, Bennett’s house, to make sandwiches, catch their performance on “Kimmel,” smoke again and, eventually, crash.  The band’s name started out as a joke, while Bennett was still a member of Odd Future, the unruly hip-hop collective that caused a frenzy in the music industry when they broke out six years ago. In 2011, a journalist interviewing the crew asked one member, Vyron Turner (who goes by Left Brain), where he was from. “He was like: ‘I hate when people ask me that,’” Bennett recalls. “‘I’m going to start saying I’m from the Internet.’” The idea cracked her up and eventually inspired the name of the side project she would chip away at in her off hours.  Turner may have been reacting to the banality of the question, but his answer also illuminated a changing dynamic for rap, which has historically been categorized by regional sounds. People Turner and Bennett’s age are defined by a completely different geography, the social networks and websites they spend their time on. Odd Future was the epitome of this new statelessness: They were neither engineered by a label nor hometown heroes, but something wildly different.  Odd Future dominated many conversations about pop culture and the future of music by the end of 2010. They had released all of their early work — a barrage of clever mixtapes, striking artwork and bizarro music videos — for free on Tumblr and YouTube. Their sound was prodigious. And not only was their music different but they also looked different too, a bunch of black weirdos who skated in their free time and moshed onstage.  The frenzy surrounding Odd Future reached its peak in 2011: Cartoon Network gave the group their own television show; plans for an Odd Future retail shop were in the works. Labels were desperate to sign deals with the group, and Sony Music Entertainment succeeded. The crew had the upper hand and persuaded the label to give them their own imprint, and to award each member a cushy solo record deal. Bennett, the D.J., got one, too.  Music came naturally to Bennett. Though her parents are 9-to-5 people — Janel is a city clerk and her father, Howard, owns a manufacturing company based in China — her uncle, Mikey Bennett, is a producer in Jamaica. (He co-wrote Shabba Ranks’s 1993 hit “Mr. Loverman.”) When she was young, the family took vacations to the island, and Bennett hung out in the studio and watched her uncle work. “At some point, I started listening to music a little differently,” Bennett said. “Rather than being like, Yo, this is dope — who made this? it started being like, I wish I made this.”  When she was 16, her parents let her transform their guesthouse into a studio, where she worked on her own songs and recorded local musicians. In high school, she took music-technology classes and piano lessons; at night, she devoured beat-making tutorials and messed around with music software. She downloaded tracks from LimeWire (a file-sharing network like Napster) and remixed them using Pro Tools and GarageBand. She didn’t need much capital to be a producer, just good Google skills and a wealth of persistence and patience.  Bennett gravitated toward artists who had pioneered brand-new sounds: The sonic spaciness of Missy Elliott, the stanky soul of Erykah Badu and the acid jazz of Jamiroquai. Pharrell Williams, the original black skater weirdo, is her patron saint. And like most kids interested in music and living in Los Angeles in the mid-2000s, Bennett knew about a teenager named Tyler Okonma who called himself Tyler, the Creator. He had a sizable following on MySpace, where he released his music. “His production drew me in,” she told me. “It didn’t sound like what everyone was making — it was different and hot.” Bennett noticed that one of the people at the top of his friend list was a kid named Matt Martin (who goes by Matt Martians). She browsed through his page, listening to the songs he posted, too. She admired his ability to create deeply complex soundscapes, and she eventually messaged him, seeking advice on ways to advance her own style.  The two became friends, trading feedback on songs, which put her into Okonma’s orbit. And when Okonma needed a place to record the early Odd Future mixtapes, Bennett offered up her home studio. She produced some of their early tracks and eventually became the group’s D.J. In old footage of early Odd Future shows, Bennett plays songs from a laptop on a table at the back of the stage. Tomboyish, in a muscle tee and a short haircut, she crackles with the manic energy that Odd Future shows were famous for. She was generally indistinguishable from the boys in the group.  From the beginning, Odd Future was meant to be a galaxy of loosely knit projects; the whole point was for the members to collaborate and spin off solo efforts. Christian Clancy, one of the group’s managers, had also been a marketing executive at Interscope Records, and around 2011 he took notice of Bennett and Martin’s tight friendship and encouraged them to start recording together. After all, they liked the same sounds: jazz, old-school slow jams, neo-soul. So they began experimenting, and these experiments would eventually lead to the formation of the Internet.  Odd Future was a rare example of a viral sensation with lasting power; the music industry is rife with the ghosts of web talents who couldn’t be repackaged as megastars. The terms of the Internet’s deal with Sony “allowed us to shape ourselves,” Bennett says. The band is artistically cocooned, trying to create, as she sees it, an entirely new style of R.&B., one that includes all types of desire. “It wasn’t a conscious thing,” she emphasizes. “I just like women.”  It was always an open secret that Bennett was a lesbian, and the indirect directness of her sexuality added to Odd Future’s wellspring of contradictions. It wasn’t a big deal because, well, it wasn’t a big deal. But Bennett frequently found herself having to defend her inclusion in the group because Okonma’s lyrics were laced with homophobic slurs and rape jokes, and her presence was interpreted as tacit approval. Bennett thought this was a bit unfair given that, as the D.J., she had the least to do with the lyrical content. “When I first heard his lyrics, I was as shocked as everyone else,” she told me. “I kept listening. I looked up to him. He was a very artistic guy, and I saw past the few words that he chose to use, and I never really felt any kind of way about it.”  In a sense, she says, Odd Future’s lack of sensitivity helped prepare her for a life in the public eye — even if it made her a controversial figure. “The gay community hated me for being part of Odd Future,” Bennett says. “They thought Odd Future was homophobic because they tend to use homophobic slang, and they were like: ‘How can you work for and support homophobes?’ But they aren’t homophobic; they just don’t really care whether you’re offended or not.”  Bennett personally related to the themes that lent Okonma’s music its emotional gravity: alienation, isolation, loneliness. She felt they shared a connection, one born of “not being a typical black kid or even a popular kid.” But eventually the hypermasculinity and caustic sense of humor wore on Bennett, who is naturally low-key. She made tearful calls to her mother from the road, wondering aloud whether she should quit. Bennett also struggled with depression, worsened by the stress of touring and feeling disconnected from her family and her girlfriend at the time. She says that no one in the group — other than Martin — seemed to care. “I couldn’t talk to any of them about it,” she says. “We weren’t all that close, and they never seemed to want to hear it.”  Not long after, Bennett began training her little brother, Travis — who goes by Taco — to take her place as Odd Future’s D.J. Her musical experiments with Martin had begun to congeal into the core of their first album, “Purple Naked Ladies,” an amorphous but promising collection of experimental jam sessions and fuzzed-out, vibey tracks. One morning while Odd Future was on tour, when the group was watching the sun crest over a beach in Australia, Bennett broke the news that she was leaving. She says it was not well received. It felt like a divorce, like a family — however dysfunctional — falling apart.  “They weren’t happy about it,” she says. “I was their get-out-of-jail-free card. It’s easy to say they aren’t homophobic because Syd is there.”  She felt ostracized by the band for a while, but a few years after the fallout, any lingering resentment or hurt feelings appear to have faded. “She went with her gut, and it worked out,” Okonma says. Okonma compared the space Bennett occupies now to Lauryn Hill at her peak. “During that time, if you were a female rapper, you were either wearing boy boxers or you had your [expletive] out on stage,” he says. With Hill, “you had a girl who wasn’t doing either, smart, could rap and was musically inclined. Syd’s more like that. She’s just being her.” After the Grammy nomination for “Ego Death” was announced, Okonma was among the first people to text Bennett his congratulations.  Bennett’s exit came at a time when gender norms were blurring. Artists now feel more emboldened to hint at sexual fluidity; it’s edgy, if not outright trendy. Musicians like Wiz Khalifa and Jaden Smith have been photographed wearing skirts and dresses. Angel Haze and Shamir have said they’re genderqueer. But being openly gay can still feel especially difficult in the world of hip-hop and R.&B., where artists who are suspected of being closeted can face harsher scrutiny. Lesbianism is often fetishized, made into a hypersexualized performance. While Young Thug can get away with wearing nail polish, female artists who give off an even slightly masculine air, like the rapper Dej Loaf, are hounded about their orientation.  Minya Oh, the hip-hop journalist who goes by Miss Info, thinks Bennett has benefited from upheaval in the industry. “I’m sure that on some level of the major-label and old-establishment industry, there are execs and agents who think homosexuality is a liability,” she says. On the other hand, she adds, “there are more and more handlers and mentors and facilitators who will see a new artist who is gay as either an opportunity to tap into a new market or, at worst, just a talking point.” But even more important than all that, Oh says, is that artists like Bennett may not even have to pander to the mainstream anymore: “As fragmented as music audiences are these days, it would be difficult to alienate fans who are already bunched into nomad tribes.”  If anything, Bennett seems to have attracted an audience that appreciates the way her onstage presence transcends any particular gender. “If you think I’m a young boy singing these songs, dope,” she says. “Run with that.” As Martin put it: “I’d rather try it and fail than have Syd singing about dudes or something.” At that, Bennett giggled and sang out: “Hell, no!”  During the handful of times we met, I repeatedly tried to talk to Bennett about the importance of her visibility as a gay singer. And every time, she seemed uneasy with the idea that she was a symbol. But she can’t avoid it — there is virtually no one else like her in the public eye. The last time I saw her, we were having breakfast at the Hotel Hacienda Cocoyoc in Cocoyoc, Mexico, a few hours before the Internet was scheduled to play a local festival in a forest, and I picked at the topic again. Did she see herself as symbolic of something larger than herself?  Bennett’s outward manner is so nonchalant and mellow it can start to seem like an affectation, but as soon as the words left my mouth, Bennett put down her forkful of pancake and slid me a sideways look, the kind you give someone when your patience is wearing thin but you still feel obligated to be polite.  “Maybe I just look at things differently,” she said to me, speaking slowly, as one might to a child who is having trouble absorbing a set of simple instructions. “I never really thought it was a thing. You know? Like I didn’t think it would be this big of a deal.” I agreed that it wasn’t and said I was simply in awe of how openly she lives her life at such a young age, when many women I know — including me — came to terms with their sexuality much later in life. The cloud lifted. Now we saw each other clearly.  The Internet — the network — has a way of normalizing fringe ideas, marginalized identities and emerging artists that old media tends to ignore. It has done such a good job, you could argue, that people like Bennett — black, queer and weird — can exist without the burden of having to represent something larger. Bennett will never be something she’s not. She’s not looking for validation from record labels, or even really from audiences. Later that night, as thousands of Mexican teenagers rushed the stage, singing along in English and screaming her name, Bennett looked completely at home, and completely herself. ♦  Jenna Wortham is a staff writer for the magazine.
A playlist by the writers Marlon James, Jenna Wortham, George Saunders, Wesley Morris, Mary H. K. Choi and others.