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When Lil Nas X triumphantly ascended the MTV Video Music Awards stage after winning video of the year, he immediately knew who to shout out.

“Okay,” he said, “first I wanna say ‘thank you’ to the Gay Agenda. Let’s go, Gay Agendaaaaa!”

Before the ceremony, the 22-year-old rap megastar — whose new album, “Montero,” (his given name is Montero Lamar Hill) debuted this month — graced the red carpet in a shoulder-baring lavender Atelier Versace suit-dress while flashing a diamond-encrusted smile. That evening he’d performed in a makeshift shower surrounded by shirtless, dancing Black men, before finally reemerging to accept his award. It was a landmark night.

“I couldn’t have imagined 20 years ago, that an openly gay Black male could be a number one artist in America,” says Kevin Powell, a longtime music journalist and activist who is working on a documentary about Black manhood. “He’s empowering a lot of invisible lesbian, gay, bisexual, transgender folks just by the fact that he’s being who he is.”

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Meanwhile, elsewhere in the rap world, another star, DaBaby, was in the process of apologizing for homophobic comments he’d made during a performance in July. The 29-year-old rapper had shouted out audience members who weren’t afflicted with HIV/AIDS and male attendees who weren’t performing sex acts with other men “in the parking lot.” The backlash was swift, and DaBaby has yet to fully recover. Concert bookers have canceled at least eight of his appearances, while past collaborators, including Dua Lipa and Megan Thee Stallion, denounced the remarks.

“I never, ever meant to offend anybody or say anything to make anybody feel any type of way live on that stage a few weeks ago,” DaBaby told another crowd via a recorded video at Hot 97′s Summer Jam, several apology attempts — and half-retractions — later. He followed the Summer Jam apology, later in the show, by calling some people who had been offended “crybabies.”

How did rap, where in the not-too-distant past artists threw around the “f-slur” without reservations, get here?

Two decades ago, at Summer Jam 2001, Jay-Z launched one of the rap world’s most enduring feuds with his song “Takeover,” by mocking another rapper, Prodigy, calling him a “ballerina” and flashing a photo on a giant screen of the rapper dressed in a dance outfit.

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In the full version of the song, released later that year, Jay-Z called the rapper Nas a homophobic slur. Nas responded with “Ether,” a track in which he dubbed his nemesis “Gay-Z” and ridiculed him for calling his record label Roc-A-Fella, rapping: “Rockefeller died of AIDS, that was the end of his chapter / And that’s the guy you chose to name your company after?”

The songs became legendary among rap fans — “Ether” was so brutal that it became its own verb in the Black lexicon (to “ether” someone is to roast them without pity) — but Jay-Z’s relationship to homophobia changed. He went from carelessly throwing around slurs to being considered an LGBTQ ally and speaking eloquently about his mother coming out to him as lesbian, while recording his 2017 album, “4:44.” “For her to sit in front of me and tell me, ‘I think I love someone.’ I mean, I really cried,” he told David Letterman in 2018. “I cried because I was so happy for her, that she was free.” Meanwhile, Nas hit the stage with Lil Nas X at the 2020 Grammy Awards to perform their song “Rodeo.”

The shift has not been universal. When the backlash hit, rappers T.I. and Boosie came to DaBaby’s defense.

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“If you gonna have the Lil Nas X video and him living his truth, you gonna damn sure have people like DaBaby who gonna speak their truth,” T.I. said in a video on Instagram. “Ain’t nothing wrong with none of it, it ain’t got to be no hate — it’s all honesty. Everybody living in their truth.”

T.I. added that he doesn’t want his children viewing Lil Nas’ performances, and that while he “respects gays,” he wonders whether gay people have more rights than heterosexual people.

By and large, though, “rappers are starting to read the room,” says Chuck Creekmur, who runs the website AllHipHop.com.

Creekmur recalls attending a Raekwon concert this year and noticing the Wu-Tang Clan rapper edit a lyric that originally contained a homophobic slur. Once the song ended, Creekmur says, Raekwon explained to the audience that he’s grown more enlightened since writing it. (Raekwon’s representatives did not immediately respond to a request for comment.)

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“Hip-hop is a true mirror of society,” says Creekmur, and society has changed since Jay-Z and Nas were trading “ur gay” jokes in 2001. Back then, Massachusetts was being sued for denying marriage licenses to same-sex couples, the Defense of Marriage Act had been on the books for five years, and George W. Bush was two years away from making a constitutional ban on same-sex marriage part of his reelection strategy. Meanwhile, the early 2000s American popular culture wasn’t much friendlier to gay people. “The 40-Year-Old Virgin,” which spent multiple weeks atop the box office in 2005, features two grown men making a series of increasingly absurd “You know how I know you’re gay?” jokes. Katy Perry’s “Ur So Gay,” a kiss off to an ex that uses “gay” as a pejorative, went number one on the Billboard dance chart in 2008.

Still, some cracks of sunlight began to show through the homophobic clouds in American pop culture. In the summer of 2002, Michael K. Williams was just beginning his star turn on HBO’s “The Wire” as gay stickup artist Omar Little, a classic performance that tried to bring more humanity to perceptions of Black men. And in 2005, Kanye West became one of the earliest rappers to urge his fellow artists to stop discriminating against gay people. Now, the Supreme Court has legalized same-sex marriage. The entertainment industry boasts more LGBTQ representation. And the hypermasculine world of rap music is being upended by a genre-bending rapper who made the biggest hit record of all time when he was still a teenager searching for his own identity.

In the three years since his world conquering smash “Old Town Road,” Lil Nas X has been expanding hip-hop’s imagination of what a mainstream Black male artist can be. Not everybody has welcomed the change. Some members of the Nation of Islam have accused him of being part of a conspiracy to “feminize” Black men. Lil Nas X has insinuated that other Black male artists have shied away from collaborating with him. “Maybe a lot of them just don’t wanna work with me,” he replied to a Twitter user who questioned the lack of Black male artists featured on “Montero.”

“You have one person versus many, many, many other people who are perpetuating the cycle of the old image” of what it means to be masculine, says rapper Open Mike Eagle. “I don’t think he’s gonna move the needle that much.” Though it can be done, it takes a while to change perceptions. He points to heterosexual artists such as Drake and Kanye West, who rap and sing about mental health, isolation and emotional vulnerability, and have expanded notions of Black manhood. They were initially met with skepticism, and in Drake’s case, mockery.

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Eagle, whose recent album “Anime, Trauma and Divorce” explores themes of mental health and manhood, says that if Lil Nas X “can inspire a younger generation of Black boys to express themselves in a different way, I’m completely with that.” But he said that he doesn’t think it should be up to artists to change the world and that the music business will have to make it its mission to have the backs of gay artists. Admittedly, he doesn’t know what that looks like, “but I know right now we’re not seeing any of it.” He said he believes corporate entities don’t really care about young Black artists, citing his disappointment with shallow gestures like posting black squares in the wake of George Floyd’s murder.

He also worries that while the industry is happy to make money off Lil Nas, the risks of carrying this burden could negatively impact his mental health.

Lil Nas X has expressed disappointment in how the industry has responded to the popularity of gay artists. “Gay artists in general are just swept under the rug, no matter how much they’ve contributed,” Lil Nas X recently told Zane Lowe of Apple Music. “It’s just like, 'oh, but, you know, but they were gay so it kind of doesn’t count.’ Looking around and seeing all these other artists who are gay and kind of just like, pushed to like this box of, this bowl of gay artists,” he continued.

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Rashard Bradshaw, who goes by the name Cakes Da Killa, at first didn’t see a path for him in the rap industry as “an effeminate gay man.”

Bradshaw says he fell in love with rap after listening to artists such as Busta Rhymes, Lil’ Kim and Cam’ron, whose flashy Harlem style was an inspiration. His first opportunity to perform in front of an audience came 10 years ago, at a Brooklyn house party. “I didn’t feel like this is something weird,” he says. “It came naturally to me. And, you know, it helps that I’m talented.”

He realized that there was room for him in rap. Since then, he’s recorded an album and two EPs as Cakes Da Killa, and is set to release a short film, titled “Visibility Sucks.”

Bradshaw disagrees with the framing of hip-hop as an inherently homophobic culture. “When you look at some of the early rappers, they look gayer than me,” he says, laughing.

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Rap gets unfairly singled out, he says. “There’s homophobia and racism in country music,” Bradshaw says. “There’s transphobia in pop music. It’s never framed like that. It’s always, ‘Why is rap so homophobic?’ ”

“It’s the people in hip-hop that make it homophobic,” he says.

While he’s not a household name, Bradshaw, 30, has been able to sustain a career by end-running the traditional hip-hop power structure — a miniature version of what Lil Nas X himself managed to do on TikTok.

“Going on Hot 97 and rapping for Ebro” — the station’s morning show host — “or doing a Vlad interview” — that’s a YouTube show — “they matter, but they don’t matter as much as they used to, because the generation has changed,” Bradshaw says. “It’s about whether or not the song is getting traction on TikTok.”

This current moment is “the last stand for this antiquated society of hip-hop,” says Marcus Dowling, a music journalist. “Now you could be five Korean kids, or a kid with a diamond in his head from the suburbs of Philly, or a gay kid with a SoundClick beat from Atlanta, who’s having all the fun.”

Lil Nas X told Lowe that he hopes that because of what he’s doing now there will be more gay rappers following him into prominence, comparing it to the current explosion of female rappers. “I feel like a decade from now, it’s going to be the same with gay rappers,” he said. “There’s going to be entire trans rappers and whatnot just killing it.”

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