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How do you think my life has been these past few months?” Shaboozey asks with a wry smile.

The 29-year-old multihyphenate artist — one of 2024’s biggest breakout acts — has twisted my question and flipped it back on me, his measured poker face masking the tornado of emotions he’s feeling. There’s no hiding that he’s tired; we’re speaking the day after September’s MTV Video Music Awards, where he snagged two nods (including best new artist), and its star-studded afterparty, where he mingled with the likes of Taylor Swift and Sabrina Carpenter. Some hours later, he went to Brooklyn for his Billboard cover shoot, soundtracked by Zach Bryan and Chris Stapleton. Now we’re grabbing lunch in a hotel restaurant, where Shaboozey has finally settled down with a half-dozen Prince Edward Island oysters and some fries.

The VMAs were just the latest marquee moment in a year full of the kind of highlights most artists dream of achieving over their entire careers. A year in which his appearances on Beyoncé’s culture-shifting Cowboy Carter (on “Spaghettii” and “Sweet * Honey * Buckiin’ ”) were just the beginning of his string of feats. A year when Shaboozey went from a supporting stint on a Jessie Murph tour to his own headlining North American tour. A year when his own “A Bar Song (Tipsy)” notched a historic 12 weeks atop the Billboard Hot 100. And a year that could still get even bigger if “A Bar Song” gets likely-looking Grammy nominations for record and song of the year; or if the album it’s on, the Billboard chart-topping Where I’ve Been, Isn’t Where I’m Going, gets album of the year and best country album nods; or if Shaboozey himself contends for best new artist.

At his core, Shaboozey (or Boozey, to his friends) exudes the calm cool of a rebel who always knew his outside-the-lines plan would lead him to glory. Still, America’s favorite new cowboy admits that he doesn’t always “feel prepared for this stuff. You just kind of get thrown in it.”

With “A Bar Song” — which has racked up over 771 million official on-demand U.S. streams, according to Luminate — Shaboozey became the first bona fide Black outlaw country star, a status he has been working toward achieving for a decade. The son of Nigerian immigrants, the artist born Collins Obinna Chibueze grew up just outside Woodbridge, Va., the second of four children. Though he spent two years at boarding school in Nigeria, Shaboozey spent most of his childhood in Virginia, including his high school years, when his football coach’s misspelling of his surname evolved into his nickname and now-stage name.

“It could be a little confusing at times,” he says of growing up Nigerian American in Woodbridge, a Washington, D.C., exurb that was markedly more rural in his youth than it is today. “Hearing your name [mispronounced] during attendance was always a thing; you felt like you had to make it easier for everyone else to understand.” Most Black children of immigrants know such experiences (microaggressions, really) well, and some are also familiar with another phenomenon that marked Shaboozey’s childhood: the endless words of support from parents who understood the importance of reminding their children of their power in a society actively trying to strip them of it. “If I’m going to do anything,” Shaboozey — whose surname means “God is king” in Igbo — pledges today, “I’m going to make sure I’m damn good at it.”

Growing up in Virginia — the home of all-time greats like Patsy Cline and Missy Elliott — also meant that Shaboozey was always aware of the intersections between diverse music genres and styles. But first and foremost, he rooted himself in his father’s playlists, where he encountered country legends Don Williams and Kenny Rogers. As a kid, “outside of MTV and BET, I wasn’t getting the specific names of the artists my parents played around the house and spoke about,” Shaboozey says. “It was all just music to me.”

He didn’t just latch on to the music his father played — he was also enamored with the aesthetic of his pop’s old photos. “Every time I saw a picture of him, he was always in Wranglers. He always gave ‘young country guy,’ ” Shaboozey recalls. From Wrestlemania to Westerns, American culture and its archetypes are exported to, and emulated in, nearly every corner of the globe. Still, most media about cowboys disproportionately features white men, which can feel incongruous to those who feel connected to cowboy culture’s actually multicultural history — and it’s for those people whom Shaboozey wanted to create a unique soundtrack.

At 19, Shaboozey moved to Los Angeles — his first time truly living beyond Virginia — with the goal of writing scripts, making movies and recording music. Shortly after, in 2014, he scored his first quasi-viral moment with his piano-trap banger “Jeff Gordon.” (Shaboozey is a big NASCAR fan.) Around that time, he was also delving into the catalogs of rock icons like AC/DC and The Rolling Stones, indoctrinating himself into the school of Prince and studying the folk roots of Bob Dylan and John Prine.

“In that [period of] discovery, I found country music to be the thing that resonated with me in a really strong way,” he says. “Me being from Virginia, me loving the style and the way of life and the things they talked about. It all seemed very peaceful. It seemed like I could be real.” Even more importantly, Shaboozey began to realize that Lil Wayne and Rogers could be complementary, not opposing, influences. Finally, he understood: “This is who I am.”

When Shaboozey first tried to launch a country album, the project bricked. Two years before the release of his 2018 debut album, Lady Wrangler, he had joined forces with writer-producer Nevin Sastry for Wrangler — which remains shelved to this day.

Shaboozey and Sastry met in 2016, and their connection was so strong and immediate that within a month, Shaboozey moved into Sastry’s apartment. Before completing the “more rap-adjacent” Lady Wrangler, Shaboozey decided to put Wrangler to the side because “something in my head told me, ‘The world ain’t ready for this,’ ” he says. In a sense, he was right. Lady Wrangler (released on Republic Records) arrived in the aftermath of “Daddy Lessons,” Beyoncé’s first country music foray that was rejected by the Recording Academy’s country music committee for the 2017 Grammys and that she performed with The Chicks at the 50th annual Country Music Association (CMA) Awards, one of the most controversial moments in the event’s history; and a few months before Lil Nas X and Billy Ray Cyrus rewrote the rules of country, pop and hip-hop with 2019’s “Old Town Road.”

“The rap we looked at on TV was always glamorized,” Shaboozey recalls. “That wasn’t the reality for everybody. No matter how much I tried, I couldn’t write music in that world. I found country music could teach people that the little things in life are where the value is. Just having a working truck that you can take your girl in to ride to a cliff and watch the sunset is enough.”

Sastry and Shaboozey have now collaborated on all three of the star’s full-length projects, but it was 2017’s “Winning Streak,” a woozy trap fantasia gilded in Western aesthetics, that helped Shaboozey land a deal with Republic and release Lady Wrangler. The label dropped Shaboozey following that album’s release (Shaboozey is tight-lipped as to why; Republic did not respond to a request for comment by press time), and soon after, the coronavirus pandemic changed the path of his life. In 2020, Shaboozey met Abas Pauti while playing basketball with mutual friends; after the two got to know each other, Pauti immediately offered to move across the country once Shaboozey told him that Virginia was the place he “needs to be in order to be the artist he wants to be” — a display of commitment that inspired the then-budding star to make Pauti his manager.

They remained in L.A., and by the following year, Shaboozey signed to indie label EMPIRE — which had previously worked with Black country artists like Billboard chart-topper Kane Brown — after a successful pitch from Eric Hurt, vp of A&R publishing, Nashville, at the company. “We understood what he was trying to do and we loved it, but obviously, it wasn’t anything that was out at the moment,” EMPIRE president Tina Davis says of her first impression of Shaboozey and his music. “It’s a feeling you get when artists on a [certain] level come into your presence. It’s kind of like the air goes out of the room. His presence was so full and prominent, I knew he was going to go somewhere.”

Standing at around 6 feet 4 with broad shoulders and lengthy wicks, Shaboozey is a dark-skinned Black man who wears his racial identity with pride. He’s a magnetic presence in any room he enters, though not in a domineering way. But his often stoic face can conceal the “manic, creative energy,” as Sastry puts it, that lies behind it — which he harnessed to finesse his sound and style going into his second and third albums.

On Cowboys Live Forever, Shaboozey joined forces with rising producer Sean Cook (one of the talents behind Paul Russell’s “Lil Boo Thang”), with whom he wrote three songs in three days. “In the studio, he likes to ride on music,” explains Cook, who later co-produced “A Bar Song.” “Sometimes he’ll get on the mic and I’ll loop the guitar, and he’ll freestyle melodies and conceptualize lyrics. Other times, he’ll sit in the booth and write the song as he goes; on the newest album, he actually brought in some guitar ideas himself.” With Cowboys Live Forever, Shaboozey intensified his country bent and enhanced his narrative-driven, cinematic soundscapes that straddle hip-hop and Americana-steeped country.

That genre-agnostic approach culminated with “A Bar Song (Tipsy),” 2024’s longest-running Hot 100 No. 1. Written and recorded in November 2023, near the end of the Where I’ve Been sessions, “A Bar Song” — which interpolates J-Kwon’s 2004 smash, “Tipsy,” and was borne out of Shaboozey’s desire to flip an aughts song — didn’t even need a final mix for those who heard it to recognize it as a hit. Pauti, who was in the studio the night Shaboozey recorded the song, immediately texted Jared Cotter, a Range Music partner who joined Team Shaboozey as co-manager in 2022: “We got one.”

For her part, EMPIRE’s Davis was so instantly enthralled by the track that she shifted her attention from getting the album to the finish line to clearing the “Tipsy” interpolation. J-Kwon, whose “Tipsy” reached No. 2 on the Hot 100, was so thrilled with Shaboozey’s country flip of his track that “he was listening to the record for three weeks straight, not clearing it because he thought the song was already out,” as Shaboozey tells it with a glimmer of childlike glee in his eye. Once J-Kwon eventually cleared the track, it primed the path for “A Bar Song” to become the first song by a Black man to simultaneously top Hot Country Songs and Country Airplay — and the longest-running No. 1 debut country single since Carrie Underwood’s “Jesus, Take the Wheel” in 2006.

Although “A Bar Song” dropped after Shaboozey’s dual appearances on Beyoncé’s historic Cowboy Carter, the whistling track was instrumental in helping him secure those coveted features. When Shaboozey performed the then-unreleased song at Range Showcase Night at Winston House in Venice, Calif., in early 2024, the crowd loved it so much that he played it again. According to Cotter and Pauti, in that crowd was one of Beyoncé’s A&R executives, Ricky Lawson, who instantly knew Shaboozey would be perfect for the record Beyoncé was then working on. Shaboozey says he was initially invited only to write on Cowboy Carter; then, Beyoncé asked him to record some verses, one of which included his freestyled outro on “Spaghettii” (with Linda Martell, which peaked at No. 31 on the Hot 100), and he appeared as well on “Sweet * Honey * Buckiin’ ” (No. 61).

The “Beyoncé bump,” as Cotter calls it, spurred Shaboozey’s team to advance the release date of “A Bar Song” a couple of weeks to April 12. “In this world of virality and quick hits, we wanted to be closer [to Cowboy Carter’s release] and be able to capitalize [on the exposure] with what we thought was a hit,” Cotter says. Early in its gargantuan run, “A Bar Song” usurped Beyoncé’s “Texas Hold ’Em” atop Hot Country Songs, making the collaborators the first Black artists to earn back-to-back No. 1s in the chart’s nearly 70-year history.

“It just feels great to see a true talent like Shaboozey win,” a representative from Beyoncé’s Parkwood Entertainment tells Billboard. “He has a clear sense of the artist he always was, and now the world knows it. To see him dominate the country space is a win for all those Black artists who have been authentically honing their craft for a long time now.”

As “A Bar Song” came to dominate the summer, it continued to help Shaboozey notch major milestones. When he played the BET Awards for the first time in June, J-Kwon joined him for a whimsical, saloon-set mashup of “A Bar Song” and “Tipsy.”

“Traditionally, I feel like country music wasn’t really accepted in that space as much,” says Shaboozey, who became just the second Black male solo country artist to play the BET Awards (after Brown in 2020). “I even felt — whether that’s my own insecurity or [self-judgment] — ‘Is this thing really connecting with people?’ as I’m performing the song. That’s my biggest fear… when I’m feeling out of place in this space. But that’s what I want to do with my music: be disruptive and show people that music is progressing.”

Shaboozey and J-Kwon’s performance was well-received — including by rappers such as Skilla Baby, French Montana and Quavo, all of whom gave him words of support at the show or hit him up in the days following. “I love hip-hop; I’m a part of their community, too,” Shaboozey reiterates — and he’s right.

Shaboozey is as country as he is hip-hop, as evidenced by the featured artists he tapped for Where I’ve Been. While Texas country-rocker Paul Cauthen helps bring the house down on “Last of My Kind” — ESPN’s new Atlantic Coast Conference college football anthem — Dallas rapper BigXthaPlug appears on the fiery hip-hop party track “Drink Don’t Need No Mix.” But while Shaboozey could promote songs from this album that don’t cater to country audiences, he doesn’t currently plan to. “Shaboozey is a country artist — that’s what he’s passionate about,” Cotter stresses. “What we’re seeing across all genres is artists don’t need to be in one box. Shaboozey is the first one that’s genuinely both in hip-hop and country music; he can rap as well as he can sing. We’re definitely going to promote that because it’s who he is. It’s not a new thing that we’re trying.”

“[Shaboozey] is a little bit of everything,” Davis adds. “That’s what separates him from everyone else. I think Taylor Swift shows that you don’t have to stick with one genre — you can try them all and push them all.”

But Nashville and its leading industry players have not been so uniformly open-minded regarding Shaboozey’s generally genreless approach, or his appearance. “They kept wondering if other songs were country on his album or if it was just going to be one song and then all of a sudden, he’s a street thug,” Davis recalls. “I think it’s both [his sound and appearance]. Obviously, if you looked at him walking by and he didn’t have a belt buckle and cowboy boots, you’d swear he was doing something different. I think it’s just the stereotype of what people see, but having those conversations and sharing the whole album made things a little bit easier.” While Shaboozey is acutely aware that he’s “definitely a new artist in [the country] space,” he says he now feels embraced by Nashville — and vows that his “next project is going to be even more country, even more dialed in.”

And Shaboozey has made inroads with the country establishment, including at a pair of country music awards shows. He scored 12 nods at the People’s Choice Country Awards and two nominations — new artist and single of the year — at the CMA Awards. At the latter ceremony, Shaboozey is just one of three Black performers to be nominated, alongside Michael Trotter Jr. and Tanya Trotter of The War and Treaty. “There’s a weight that comes with it,” Shaboozey acknowledges, adding that Michael personally called to congratulate him — and also to recognize that “Man, it’s just us.” (Significantly, Beyoncé and Cowboy Carter didn’t receive any CMA nominations. “All I know is that she made a great body of work and I know she’s proud of that,” Shaboozey says of the snubs.)

The crossover success of “A Bar Song” has conjured comparisons to “Old Town Road,” another country-rap joint that ruffled more than a few feathers back in 2019 — and Shaboozey has found kinship with Lil Nas X. “That’s the homie,” says Shaboozey, who connected with Lil Nas at the previous night’s VMAs. “We haven’t had deep conversations, but I can tell what’s happening to me now is probably very similar to what he experienced.”

For Shaboozey, the VMAs were a “fishbowl” experience, where he was aware of outsiders looking at Lil Nas and him, waiting for the two to interact and acknowledge how their stories intersect. “It’s like everyone is like, ‘Do they know?’ ” he quips. And while the VMAs are technically genre-agnostic, Shaboozey did feel a bit of a disconnect with the audience. “Love the VMAs, but sometimes it felt like they weren’t there for me, to be honest,” he says with a droll chuckle, noting how some audience members seemed almost embarrassed to cheer for him after screaming for more top 40-facing pop stars. “But there were more Black folks and people working the event that were showing me love, and that’s what it’s about.”

He knows, however, that these awards shows are all a prelude to February’s Grammys. In addition to best new artist and record and song of the year for “A Bar Song,” Shaboozey will likely contend for best country song and best country solo performance. Should he take home a trophy in the country field, he would become just the fifth Black act to do so, joining Charley Pride, The Pointer Sisters, Aaron Neville and Darius Rucker, who tells Billboard, “We’re fortunate to have Shaboozey in country music.” Shaboozey’s team confirms that it will submit Where I’m From and its songs in the country field, and the campaign includes stops at “the right looks,” according to Pauti, including The Late Show With Stephen Colbert (where he recently performed his new single, “Highway”), a sit-down interview with Gayle King, an intimate L.A. showcase and meeting Recording Academy CEO Harvey Mason Jr.

“I think it’s something for me to bring home to everybody,” Shaboozey muses about his potential first Grammy wins. “This is the peak of the mountain as far as recognition comes. This is a long-standing ceremony, it’s history and tradition, and hopefully we’re able to take it home. That childhood fear of never winning anything is still there. It would mean the world to win one of these things, but if not, the year we had was crazy. If not now, it’ll come. We in the club now.”

“The Grammys are always going to matter to me,” says EMPIRE founder Ghazi, whose commitment to a genreless future brought him out to Nashville years before he crossed paths with Shaboozey. “From being a 14-year-old making my first records to now being a seasoned executive, I never lost sight of that journey, and the Grammys never [lose their] luster.”

As Shaboozey picks at his final few French fries, I take in the man sitting across the table from me, who, though he’s currently relaxed in the booth of a Brooklyn eatery, has more than a little of a classic gunslinger’s gleam in his eyes. When he picks up his final oyster, it feels nothing short of poetic. A few years ago, it would have been borderline unimaginable to see someone like him at the zenith of country music, yet here he is — reshaping signifiers of so-called authenticity and injecting them with the street-smart swagger of the contemporary hip-hop gangster. A distinctly 21st-century manifestation of the spirit of Marty Robbins, channeled through a voice and persona equally steeped in Stanley Kubrick, Garth Brooks and Juvenile, Shaboozey is a lone star — a true outlaw who has effectively rewritten the rules of a land that’s actually his to reclaim.

And like any genuine outlaw, he never breaks eye contact while making plain his message: “I’m just making music I love,” Shaboozey says. “It’s cool being recognized, but I’m making music for a group of people that are usually underrepresented. I’m going to keep doing that. It’s good to be that guy — those are the people who are remembered.”

This story appears in the Oct. 5, 2024, issue of Billboard.