Richard Ruperto wakes up in the morning with one goal in mind: to become a hip-hop sensation. He's been hustling for years, tirelessly releasing mixtape after mixtape, remix after remix, and maintaining a large social media presence without the dozens-deep entourages rap stars typically have. A lifelong resident of the projects of Spanish Harlem and raised by a single mother, Ruperto regards his community with the diehard devotion of a mayor. He wants to give back to the people of Spanish Harlem, get his mother a nice apartment, and sign a record contract with Young Money. Ruperto's bio is not too different from those of other hip-hop artists—he wants to use his music to tell his story and give back to his neighborhood and the people in it who gave him the strength to succeed. And that's where this story takes a turn: Richard Ruperto, also known by his stage name, Loco Ninja, is openly gay. In the world of hip-hop, where "faggot" is still a common diss track insult and machismo reigns supreme, Loco's sexual orientation is quite possibly the greatest commercial disadvantage possible. To date, no openly gay male hip-hop artist has signed to a major record label. While there have been some successful female rappers who identify as LGBTQ—Lady Sovereign and recent breakthrough rapper Azealia Banks have been open about their sexualities in interviews—out male rappers have had a harder time breaking into the community. This is a business standard that is not difficult to understand within the context of a musical culture in which "no homo" is still a common tagline and chief figures ranging from Chuck D to Eminem have, at some point or another, declared their discomfort with the gay community. Yet, within American culture, discomfort with homosexuality is beginning to wane. In 2011 alone, the gay community gained the right to marry in New York, saw the repeal of "don't ask, don't tell," and won the support and acceptance of the largest percentage of the population in years. In the realm of rap, Lil B pushed the community out of its comfort zone by titling his latest LP I'm Gay (I'm Happy), forcing listeners to re-examine the cultural connotations of the term. Big names like Kanye West and the Game voiced and tweeted their support ("Who run the world? Gays!" said the latter, putting a spin on the Beyoncé smash to indicate a larger acceptance of the LGBTQ community). In the past decade, more and more gay artists have entered the rap world, each declaring their intention to be "the one" to break into the mainstream and challenge the archetype of hip-hop success. They know that the cultural momentum is shifting and that now is the time to act—by re-defining traditional interpretations of the genre, by releasing quality material on a constant basis, and by reaching out to new audiences while holding on to the support of the communities that accepted them. So, is the day a gay hip-hop star graces the cover of XXL in the near future? The answer to that question is not entirely clear, but one thing is certain—the status quo of hip-hop is being challenged in an unprecedented fashion. The Masculine Ideal How did we get to "no homo?" To understand the cultural incongruity between hip-hop and homosexuality is to dig into the core of the art form itself—not a retrospective glance but a trip back in time, before hip-hop was epitomized by extravagant music videos, harems of scantily clad women, and champagne fountains. Former MTV producer and entertainment executive Terrance Dean published the most widely read book on the subject to date: Hiding in Hip-Hop, a revealing account of famous gay men's lives in the music world. Dean himself has spent the past 15 years working with the likes of Spike Lee and Rob Reiner and producing live award shows and events (including, notably, the MTV Video Music Awards and VH1's Hip Hop Honors)—he is also openly gay. In his book, Dean sets out to prove not only that members of the LGBTQ community were involved in the emergence of hip-hop but that they have been instrumental throughout the process: not simply as artists but also as producers, managers, and other executive positions. Dean attributes the origins of homophobia in hip-hop to the masculine nature of the art. He defines hip-hop as a reassertion of pride and power in the wake of recent political victories, but also as an attempt to reverse the political and cultural emasculation begotten by the civil injustices of decades (and centuries) past. "For so many years, we people of color have not had anything to claim as ours," Dean says. "Hip-hop was a badge of courage, our chance to say, This is ours—it belongs to us.' We have been emasculated so long as a people. It goes way back, back to the days of slavery—it was an emasculating experience, especially for the men. We'd been stripped of our manhood. We didn't have anything. Now we have something, and people in the community equate homosexuality with the loss of what we tried to gain back: our masculinity." That masculinity is framed and displayed by the music video, a medium that Dean regards as a major shaping force of hip-hop's identity and image—and, even more importantly, as a visual representation of the values and ideas held by urban communities. "Before, the black community had made its claims in music—jazz, R&B, soul—but there was no visual outlet," Dean says. "And then MTV and BET came along, and people began to see images of who we were as a culture, and a visual representation of the lyrics and the experiences inherent in them. It gave people a glimpse into what the African-American experience looked like: how people live every day, how people make it. With the rapper in the music video, we see someone who's done that, who's managed to have it all." The experiences shown in music videos epitomize stereotypical male fantasies of power and wealth: 50 Cent's "Candy Shop" comes to mind, with its literal housefuls of women and candy-painted Lamborghinis surrounding the mink-coat-clad rapper. Then there are the classic videos of gangsta-rap mainstays like Ice Cube and Mobb Deep, where the only thing more plentiful than guns is the number of times the artist mentions them. "So many men use this as a way of saying, 'For me to take charge of my art, I need to represent myself in this machismo, manly way,'" Dean says. "For many rappers, success is equal to how many women you have. It's showing how much testosterone you have. It goes hand in hand with having a criminal record or selling drugs. It's all about the masculinity." However, some experts are quick to point out that the male typologies present in hip-hop are not exclusive to the genre. Dr. Shanté Smalls, a founding member of hip-hop duo B.Q.E. and an English professor at Davidson College, doesn't consider hip-hop to be intrinsically male and points out that "we often forget that rap music and hip-hop culture involve aesthetics, business interests, and a host of compromises." Rather, she attributes the masculine nature of hip-hop to an economic model. "If you look at the music industry in general, you can see the overwhelming maleness of that industry, and it seems to like to replicate itself, not because music is intrinsically male, but maybe because capitalism is," she says. Breaking Boundaries and Changing Scenes Despite theories on the origin of hip-hop's relationship with masculinity, one thing is certain—it's a great way to sell CDs. Starting in the late '80s and continuing today, record executives' primary marketing strategy has been an arms race in which rappers compete to see who is the most "thug." It isn't hard to test this theory—you could do it right now by turning on MTV Jams or BET and keeping a mental tally of the number of machismo elements that pop up. Thirty seconds into Tyga's "Rack City" clip, you'll probably lose count. But aside from a proliferation of such values in songs and videos, hip-hop's unwavering allegiance to a "hard" lifestyle has resulted in a market where anything less is mockable, or worse, unmarketable. Gay artists thus found themselves in a difficult decision: to stay in a camp that would likely remain hostile for an indeterminate number of years (a decision often associated with remaining in the closet, since as of the day that this article went to press, no major hip-hop label has signed an openly gay rapper), or to abandon the traditional path to mainstream success and craft a new sound, aesthetic, and audience. Admittedly, this is not exclusive to male rappers—a similar dialogue ensued when female MCs like Lil' Kim became widely known. The Boston-born, NYC-based rapper known as Cazwell is perhaps the best-known example that the latter choice is not only possible, but also personally, financially, and artistically sound. After several unsuccessful attempts to break into Boston's hip-hop scene, he moved to New York City and crafted a sound that he describes as "if Biggie ate Donna Summer for breakfast"—a hodgepodge of classic hip-hop, club, pop, and disco. Cazwell, who has repeatedly rejected the label of "gay rapper," is best known for his 2010 single "Ice Cream Truck," a summery club hit with an equally sweltering video (the underlying premise, the rapper says, "is 12 dudes who live in a shitty apartment with no air conditioning"—and who cool off by eating ice cream and provocatively dancing). The video's two million hits are an addition to Cazwell's already impressive list of accomplishments: opening for Lady Gaga and cutting tracks with underground dance darlings Amanda Blank and Peaches. Other LGBTQ rappers reject the pop-rap stylings of today and instead opt for a sound that recalls the golden days of hip-hop in the late 1990s. The most notable example is Deadlee, a Los Angeles MC who resembles a Latino Tupac, with politically aware lyrics and a harder flow over mainstream accessibility. There's also local rapper Lester Greene, whose recent single "Russian Roulette" brims with the tension and rage that the title suggests. "The thing about me is a lot of people don't even know I'm gay," Greene says over the phone, the Brooklyn traffic booming in the background. "I had an audition with a casting director, and we were talking about my music, and when I told him I was gay, he was floored." Greene, along with many others, hopes to change the definition of "gay rapper" by breaking down barriers. Hartford-born, New York-based rapper Bry'Nt defines a commonly held concept of a gay rapper as "having high-pitched voice and wearing a boa." But barriers also include commercial roadblocks created by the hesitance of major labels to sign openly gay artists. "I'm trying to expand my brand," Greene says of his ventures in film and television. "I'm trying to do a little of everything so that people believe in me, and people know that I'm making things happen." Greene has appeared in a Dr. Pepper commercial, an HGTV show, and even an army training video. While he jokingly describes these ventures as ways to pay the bills, there's a bigger takeaway. These are artists who not only understand the commercial and cultural challenges they face but also respond to these roadblocks with a degree of entrepreneurship rarely seen in the rest of the hip-hop community. It's a strategy Loco Ninja knows well. "I've been hustling for years—reaching out to every producer, every DJ, anyone who will help me get my sound out." Outside the realm of music, Loco has appeared on The Tyra Banks Show, the MTV series Sex...With Mom and Dad with Dr. Drew, and PBS's Out in America. Although the exposure has helped to reach broader audiences, Loco still hasn't managed to move out of his small apartment in East Harlem. "I'm still living in the projects. I used to get jumped on that street all the time"—he motions to a street corner near his neighborhood high school—"so every day, I just wake up asking myself, What can I do today to get that record deal? How can I make this day the day?'" That day almost came earlier last year, when Rainbow Noise, an LGBTQ collective of which Loco Ninja was a member at the time, had their track "Imma Homo" featured on major rap website WorldStarHipHop.com. A Warner Bros. executive, hoping to cash in on the success of LGBTQ-positive stars like Lady Gaga and Nicki Minaj, expressed interest in the group, going so far as to offer Loco Ninja a separate, 10-year contract. The deal fell through for legal reasons, but the experience gave the rapper a lesson in reality: that at the end of the day, while record executives are watching gay artists amid the stirrings of a cultural sea change, the music business is still, well, a business. Waiting for "The One" In the past year, the LGBTQ community has made great sociopolitical strides, at both national and local levels. But will this accepting uptrend result in a mainstream openly gay male rapper? Many artists within the scene contend that it is only a matter of time until such a rapper signs to a major label and breaks down the barriers of gender like Eminem did with race at the beginning of the millennium. But he will also need to have the mass appeal necessary to convince skeptics and allies alike. "It'll take an actual artist to come forth and represent a different ideology," Dean says. "When people think 'gay,' they think of RuPaul, or Lady Gaga, or so forth. They never see someone that could look like them, or a 50 Cent, or a Jay-Z, or a Lil Wayne, with a rough exterior and admit that he is in a relationship with another man." You could call it the biggest intergenre competition of the moment. Every gay rapper wants to be the one who strikes gold (or, more fittingly, platinum), and confidence is key. Each of the artists I spoke to mentioned their conviction that with an "it" factor setting them above the rest, they might just be "the one" to grab the ear of execs and DJs. There's Cazwell with his catchy pop hooks and fun persona. There's Lester Greene, whose skills as an MC are matched only by his versatility and commercial know-how. And there's Bry'Nt, whose endless touring schedule has brought him support from within and beyond the club scene. Loco, meanwhile, thinks that his story will be his biggest asset. "Hip-hop is all about the story—it's about the hustle," he says, only a few feet away from the recently refurbished schoolyard where he was jumped as a teen. "I'm still in the projects of New York City. It's time to speak up and tell my story for the people who are from this neighborhood and all around the world." It's difficult to determine whether society will be up to the task of changing their long-held definition of the term "gay rapper," and whether the widespread tropes of masculinity will be able to progress at the same rate as national dialogue on the subject. But Smalls remains optimistic. "It will probably take XXL less long to put a queer person on the cover than it took Vogue to put a black woman on the cover," Smalls says. She hopes that hip-hop crew Odd Future member and openly lesbian DJ and producer Syd the Kyd's record deal with SONY RED demonstrates that the industry is shifting in a more LGBTQ-friendly direction. Loco is convinced that if he signed with a major label, he would receive floods of angry petitions from the silent majority the second he put pen to paper. He still contends with swarms of virulent YouTube comments—evident manifestations of homophobia in an audience in transition. But it doesn't deter him or any of his peers. "I want to stand up for the people who have been through tough times, show them that they shouldn't be afraid," Loco says. "I'm done with being scared. This is who I am, and I'm not going to change for anyone. My life is hip-hop. I do this for my family, my community, for New York." In the world of hip-hop, it would seem that stagnation is giving way to motion, taboos turning to talking points, and established truths turning out to be little more than defunct definitions shaped by a categorizing culture. As the record industry continues to crumble under the Internet's grasp, it's become more and more evident that maybe this isn't about a record deal. It's something bigger. It's a chance to express oneself on a national stage without fear of ridicule; it's a chance to reshape the world's impressions of not just hip-hop but gender and musical identity; and, perhaps most importantly, it's a chance to reach out to audiences in the hopes that "It gets better" will be understood outside of the context of a YouTube video.