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Lil Nas X
Photo illustration: Erik Grice

Lil Nas X: The Road To Montero

A week-long celebration of our favourite Lil Nas X moments.

by Ben Boddez

From the moment he arrived on horseback and implanted that inescapable country-rap melody in our collective heads, we knew that we were witnessing the birth of a cultural titan. While it would have been easy for a track like “Old Town Road” to fall back into novelty song territory and relegate Lil Nas X to one-hit wonder status, his knowledge of Internet culture and undeniable talent for marketing took things in an entirely different direction. 

By the time he came out as gay to his millions of Twitter followers, picked up a couple Grammys in his pink Versace cowboy outfit, and started fully expressing his true self in visually stunning and endlessly imaginative music videos and live performances, Lil Nas X morphed into a highly important figure for many who had never before seen anyone like him dominating the worlds of pop, hip-hop and country music at the level he has. Racking up more than 55 million monthly listeners on Spotify, praise from legends like Elton John and Diddy, and 19 weeks on top of the Billboard charts with “Old Town Road” – the all-time longevity record – Lil Nas X is here to stay.

As the pivotal provocateur gets ready to finally drop his debut album, Montero, on September 17, we’re taking a look back at some of our favourite moments from throughout his career that led us up to this point. Stay tuned all week as we take you down what we’re calling the Road to Montero. 

May 13, 2019
Lil Nas X Meets Nardwuar

A month after his breakout single “Old Town Road” ascended to the top of the charts for the first time, Lil Nas X didn’t have to wait too long to get the Nardwuar treatment. Seeming uncharacteristically uncomfortable with the spotlight in his earlier days, he spoke about everything from his favourite childhood restaurants to his hatred of the MLA citation format and dubbed emojis “the best thing of all time to ever exist” in his interview with the eccentric Vancouver legend. In return, the Human Serviette provided him with a cowboy-adorned belt buckle from Calgary.

July 7, 2019
Cooking Lessons With Chef Gordon Ramsay

In another of his masterful marketing moves, as his second single “Panini” ascended the charts, Lil Nas X persistently fired Tweets towards celebrity chef Gordon Ramsay for days in hopes that he would teach him how to make the perfect sandwich. Finally inviting him to his London restaurant, Lucky Cat, the famously foulmouthed chef dramatically quoted the song’s chorus – with added expletives – as he stared with laser focus at his sandwich maker and prayed that the finished product wouldn’t be “a meanie.” Lil Nas X later said that the only thing that could have improved this meeting between titans would be if Ramsay had yelled at him more. 

May 29, 2019
Old Town Road Becomes a Children’s Anthem 


At the peak of “Old Town Road”-mania, the endless memes, TikTok dances and news coverage of its multiple remixes and alternate versions that Lil Nas X released to keep the song trending as long as possible even saw it trickle down to the youngest children. They latched onto the catchy tune about barnyard animals just as quickly as “Baby Shark.” In response, Lil Nas X staged a surprise performance at Mayfield Heights, Ohio’s Lander Elementary, where the kids drowned him out by screaming every lyric and turned the school gymnasium into a mosh pit. The performance itself was set up by Lil Nas X casually replying on Twitter to the school principal’s video of the kids enjoying the song.

November 21, 2019
Going Undercover

In what still stands up as one of his funniest interviews to date, Lil Nas X takes his trademark deadpan sense of humour to GQ’s “Actually Me” series to answer online commenters’ most pressing questions. He shoots his shot at artists like SZA, Drake, and Rico Nasty when talking about dream collaborators while on Twitter and Instagram, but the video’s greatest moments come when Lil Nas X is instructed to mine the depths of question-and-answer website Quora, where he struggles through both incredibly obvious questions and existential pondering about his contributions to culture-shifting. 

January 26, 2020
Lil Nas and Big Nas

After his massive breakout year, Lil Nas X was able to ride his momentum and follow the Old Town Road all the way to the 2020 Grammy Awards, where he picked up six nominations, including Album of the Year and Best New Artist, and walked away with two wins for Best Pop Duo/Group Performance and Best Music Video (both for “Road”). The highlight of the evening’s show, however, was his performance. After a medley of the track’s many remixes that featured BTS and “yodel kid” Mason Ramsey, among others, New York legend Nas himself, the inspiration behind Lil Nas X’s name, joined him for a new remix of “Rodeo” that was released after the event. 

November 13, 2020
Going Digital 

While artists like Travis Scott, Marshmello and Ariana Grande have all lent their talents to concerts in the video game world of Fortnite, Lil Nas X went in another direction and performed a set in Roblox, which, for the uninitiated, is essentially Minecraft with a chat feature and less opportunity for monster-induced demise. Making sure to censor his more scandalous bars for his younger audience, Lil Nas stomped around as a giant virtual avatar, his costumes and the environment changing behind him as he ran through “Old Town Road,” “Rodeo,” “Panini” and “Holiday.” 

April 14, 2021
Arts & Raps

Although Lil Nas X consistently proves his tried-and-true connection with the younger generation, being forced to take uncomfortable questions from them on “Arts & Raps” – a YouTube show where rappers are quizzed by the unfiltered minds of children while doing art projects together – seemed to briefly strain his patience. After exasperatedly laughing at the host’s scatterbrained stories of literally being locked in a closet after getting candid about his coming out story and uncomfortably fielding questions about industry plants and, for some reason, Quavo and Saweetie’s strained relationship, there were some genuinely heartwarming connections made as the kids dubbed him an inspiration for unapologetically being himself. 

May 22, 2021
Ripped Pants

Ever the consummate professional, Lil Nas X masterfully played off an embarrassing wardrobe malfunction while performing “Montero (Call Me by Your Name)” during his debut on the storied Saturday Night Live stage. While dancing around the famed pole from the track’s controversial video, the fabric of Lil Nas X’s pants simply couldn’t hold out, forcing him to spend the rest of the performance stationary and holding it closed – though viewers may not have even noticed due to him keeping his cool. Thankfully, in subsequent performances it seems that Lil Nas X decided to forego pants entirely, evolving his fashion ambitions by wearing skirts instead. 

July 19, 2021
Satan Shoes

Translating his marketing skills over to capitalizing off some of the more backwards reactions to his presence in pop culture and the return to an era of “Satanic panic” spurred by his “Montero” video and merchandise, Lil Nas X mocked reactions (and a small bit of genuine legal issues!) to his Nike “Satan Shoes,” which contained a real-life drop of human blood, by pretending he was in serious legal trouble and going to court on Twitter for a couple days. The whole thing amounted to a courtroom skit promoting his next single, “Industry Baby,” where Lil Nas X finds himself in jail in the accompanying music video.

August 30, 2021
Pro Skater

After yet another of Lil Nas X’s Tweets caught national attention when he pointed out a double standard in the reactions to his Satan Shoes and legendary skateboarder Tony Hawk selling skateboards adorned with his own blood, he quickly made it clear that there was no bad blood between them by facilitating another meet-up between two pillars of their respective industries. In a hilarious viral TikTok, Lil Nas X appears poised to drop into a skate park, a quick edit switching him to Hawk at the last second.