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Lil Nas X Documentary: An Intimate Portrait of a Cultural Pioneer

We spoke with the directors behind ‘Lil Nas X: Long Live Montero,’ premiering on HBO on January 27th
Photograph by Courtesy of HBO.

Lil Nas X cuts an imposing figure. In a gold net tank top that shows off his ripped physique, ballooning brown parachute pants, sky-high heels, and 30 inches of ironed flat hair, even if he wasn’t making an entrance at the premiere of his documentary, Lil Nas X: Long Live Montero at the Grammy Museum in DTLA, all eyes would still be drawn to him. The tallest person in the room and studded with bling, the Grammy Award-winning rapper’s outrageous yet flawless style makes him larger than life. This image is a great match for his record-breaking music, which resonates with his fans as much as it enrages his detractors. This version of Lil Nas X is a significant part of the documentary. Just as present in the film, however, is Montero Lamar Hill, the person behind the persona.

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Shot in verité style, Lil Nas X: Long Live Montero takes place during his 2022-2023 tour of the same name. Grammy-winning and Academy Award-nominated director Carlos López Estrada (Raya and the Last Dragon) and director Zac Manuel (Time), a Sundance favorite whose specialty is intimate portraits and Black masculinity, worked in tandem.

Considering how much of Lil Nas X’s communication is on social media – which even he himself admits in the film – it’s refreshing to have this kind of access to him. Lil Nas X’s most revealing moments come when he is speaking from his bed, his chest bare. But we also watch him vomit right before getting on stage, discuss scheduling his pre-show bowel movements, and agonize over whether he can handle wearing a super-short kilt and LGBTQIA+ Balenciaga T-shirt to greet his family.

Switching back and forth in time, Lil Nas X: Long Live Montero has its share of flashbacks, but it isn’t an origin story. Much of his backstory is common knowledge. He is named after the Mistubishi Montero. He came out to the world at the height of the popularity of his breakout hit, “Old Town Road,” the reigning record holder for longest running Billboard Hot 100 No. 1. An absolute megastar, his rise was during the pandemic. He performed on some awards shows, but the Long Live Montero Tour was his first time ever playing in front of a concert audience—and the first time he experienced protestors outside the venues. He sent them pineapple pizza. When Lil Nas X: Long Live Montero premiered at the Toronto International Film Festival in September 2023, there was a bomb threat.

Photograph by Courtesy of HBO.

López Estrada originally worked with Sony Music on the conceptual side of the Long Live Montero Tour creating a theatrical presentation that also had a narrative element to it. As the show took shape, the decision was made to document the experience, not just as a concert film, but also from a personal aspect. Manuel was brought in to go behind-the-scenes, turning a personal lens on Lil Nas X. 

“There wasn’t a lot of pre-production or planning,” says Manuel. “I was documenting day-to-day, asking questions on the fly, trying to figure out what a potential story could be. If there was anything that felt narratively rich that I could latch onto, I would write a small treatment and send it off, see what they thought, jump back in and keep going.”

Despite this, Lil Nas X: Long Live Montero not only comes across as pure cinema verité, but the subject himself seems like he’s 100% on board with the whole process. But, Manuel says that’s not how it started. “My process initially was pretty confrontational, but not in a bad way,” says Manuel. “I wanted to be less of a person who’s capturing his story as a filmmaker and more getting to know him.”

The directors worked with the editor of Beyoncé’s Homecoming and Renaissance, Andrew Morrow, who is an expert at storytelling through live performance and the elements that go into creation of a show. “[Morrow] was able to create narrative threads and connections,” says López Estrada. “After he got through it, it was elevated emotionally. He really crafted this film with us.”

The film has three acts: Rebirth, Transformation, and Becoming. There is a marked difference in the first act, which illustrates just how young Lil Nas X still is. The filming style has the feel of footage captured by a close friend on a flip phone camera. His vulnerability and insecurity are on full display, as is his fan status as he shows off a massive wall of photos in his home, his “pop culture collage,” and talks about fanboying over Viola Davis at Erewhon. In contrast, to quote one of his fans, “He’s very important for the culture right now.”

The second act exhibits a more official filming style. His family enters during this act, and with that, Lil Nas X’s discomfort about his sexuality around them escalates. This act also shows Lil Nas X’s rise including Madonna hamming for the cameras backstage at one of his shows. The show itself features fantastic set designs, elaborate and ornate, not unlike Louis XVI’s court. This is perhaps a nod to Madonna’s “Vogue” performance at the 1990 MTV Awards. López Estrada and Manuel admit that Madonna’s 1991 documentary, Truth or Dare, was an inspiration.

A standout part of Lil Nas X: Long Live Montero is the expressive choreography and his dynamic dancers–not unlike Madonna dancers during the Blond Ambition World Tour. All young, Black, and gay, they are a lot more comfortable with who they are than Lil Nas X. The third act pivots around him coming to terms with all sides of himself. As Lil Nas X says, “I’m the most myself around the dancers.” Elsewhere he says he is, “Inspired by them, love them, see them as friends,” and, “They help me understand me more.”

“Nas going through this incredibly personal, incredibly emotional ride needed to have allies and needed to have someone to experience this with,” says López Estrada. “His team is there, his managers, agents are there, he has a family of people but having other Black, queer, young people who had been doing this for longer than him, all of a sudden, he had a family of kin souls that became his real family for the length of the tour. It was a beautiful thing.”

The positive impact Lil Nas X has had on his fans’ lives and the community he has created is never more apparent than in the segments where they are interviewed which play like confessionals and testimonials rather than talking heads.

“[Lil Nas X has] really reinvented how an artist gets to interact with their fans,” says López Estrada. “He’s used social media in ways that very few artists have. He’s created a direct dialogue. In meeting so many of his fans, we realized how profound of an impact he’s had in their lives. People who’ve learned to think about themselves and love themselves in ways they didn’t before being exposed to him. It’s one of the most unique things about him as an artist.”

The crowd shots show a genuinely diverse audience, but one that shares a deep connectivity. “It felt like being in a support group,” López Estrada says of the Long Live Montero concert. “Everyone was excited to feel connected and to be able to express themselves to the greatest of their abilities. People are wearing stuff they wouldn’t normally wear and celebrating each other for being open and fearless. It was really moving. To be in the middle of that and seeing thousands of people being so nice and so sweet and so caring toward one another, I had never seen anything like it.”

By the end of Lil Nas X: Long Live Montero, there is a shift to maturity. To quote him in the film, “I consider myself ‘home.’ This year has been the best for me becoming an adult”—yet he still clutches his stuffed animal, Bronco, which he refers to as his son and which has been an endearing constant throughout the film. Ultimately, Long Live Montero is about the evolution of Lil Nas X as a person through his art. To paraphrase him post the Grammy Museum screening Q&A, what he wants from the film is for, “People to see me as a person and not the online troll that I am.”

Lil Nas X: Long Live Montero premieres on HBO on Saturday January 27, 2024.