Sean Kingston: Call It a Comeback

Out of the spotlight for most of the last decade, Sean Kingston is readying a second act
Credit: Empire

How long until opportunity meets preparation?

There’s no better time than the present, if you ask Sean Kingston, the Jamaican-bred pop mastermind behind one of the most instantly recognizable hit songs of the 2000s, “Beautiful Girls,” which ascended to the No. 1 spot on the Billboard Hot 100 while Kingston was just 16 years old. Go to your favorite festival today and you’re bound to hear it between sets as the DJ keeps the crowd engaged: “Damn all these beauuuuuutiful girllllllllls.” The list of artists who have burst out of the gate and charted at No. 1 with their debut single is littered with music legends: Beyoncé, Whitney Houston, Britney Spears. Sean Kingston is on that list. Yet, despite the turbulence of his last decade, it somehow feels like he’s just getting started. 

“It was Turlock, California. They were insane. And it was like 7,000 people,” Kingston tells me, as he earnestly recalls a recent stop on his Road To Deliverance Tour during a weeknight Zoom call. He’s got mostly major cities on the docket, like Atlanta, New York and Washington D.C. But he couldn’t stop raving about the energy he received from one of the smaller crowds on the tour, in Turlock. “They were losing their minds. People were waiting by the bus for pictures!”

Kingston arriving at the 2007 American Music Awards at the Nokia Theatre on November 18, 2007 in Los Angeles. (Credit: Stephen Shugerman/Getty Images)


The clock reads 6:00 p.m. EST, but it’s the middle of the afternoon in Los Angeles where Kingston is currently based, and he rightfully sounds like he’s in the exciting midst of executing a plan. His new single, “Ocean Drive,” is to be released three days later, on July 22, and it will mark the start of something new for Kingston as much as it will represent somewhat of a full-circle moment. “Ocean Drive” features Chris Brown, with whom Kingston worked with during the early portion of his career. Now, all these years later, they are together again as Kingston enters a new phase of his life and career. 

“I’ve worked on so many records with him, even if it’s like me writing his songs or, I mean, co-writing songs for him or just being us, spending time together every day,” he says of working with Chris Brown, who recently released his 10th studio album, the somewhat self-titled Breezy. The two joined forces for 2013’s “Beat It,” which also featured Wiz Khalifa and became a modest hit, peaking at No. 52. “That’s been one of my closest people since I came in. So I’m excited to just be back, you know, doing music…”

“Ocean Drive” is a welcomed reintroduction to Kingston, who doesn’t at all sound as if he’s lost a step. His voice is crisp and bouncy, his cadence as compelling as ever. “Ocean Drive” will immediately feel familiar, and instantly track as a high-quality version of the island-inspired records that have dominated the pop circuit in recent years. Whether that will work to Kingston’s benefit remains to be seen. Though he considers himself a pop artist, it was his unwavering duty to push his Caribbean influence to the forefront—forcing radio to reckon with island tempos and cadences—that put him on a distinct path to early stardom. Time will tell, and his upcoming project, Road To Deliverance, should be a strong indicator. 

The EP is set to release in the coming weeks, Kingston’s first project since the release of his third studio album, Back 2 Life, in 2013. It will serve as a precursor to a full-length LP, Deliverance, that will mark a full decade since Kingston has had an album in stores, presuming a 2023 release.

That said, he isn’t waiting until then to pull out the stops. From Damian Marley to Trippie Redd and Youngboy Never Broke Again, Kingston has already locked in with marquee names to reintroduce himself and his music to the mainstream circuit. “I’ve been away for a little bit, so I feel like now? It has to be a culture shock,” he recalls about being motivated to collaborate with a newer class of artists. Many of his collaborators who were prevalent during the early portion of his career have since been dormant. Acts like Juelz Santana, Fergie and Kardinal Offishal, who all appeared on Kingston’s self-titled debut album, have mostly settled into the legacy phase of their careers, and Kingston has used his sharp ear to find their pseudo-equivalents, picking prolific artists from a litany of genres to co-star with him on Road To Deliverance.

It’s impressive, frankly, that after what most would consider a decade of inaction, Kingston is able to step in seamlessly with artists who were being pushed in strollers when he first topped the Billboard charts. Redd and Alabama upstart NoCap join Kingston for a viscous R&B jam that’s just nostalgic enough to trigger memories of Kingston’s early dominance. Elsewhere on the EP, Kingston flies solo for a song called “Whisper,” which sounds very much like you’ve just stepped off a plane in the tropics. Whatever of the pop formula that’s governed much of the streaming era’s output, Kingston’s musical DNA continues to pledge allegiance to his culture. Holding fast to that should pay dividends for Kingston down the road. There’s little to dislike about Road To Deliverance, and much to look forward to. Deliverance, the eventual full-length album, could make for quite the event.

Part of the reason for this, Kingston mentions, is the support from his partners at Empire Distribution, Records and Publishing, which has steadily helped create independent success for premier artists in the last 10 years. Originally a humble operation known as a proving ground for artists working on their star turns, Empire has developed into a primary destination for artists at varying points in their careers with modest-to-massive audiences looking to secure larger profit shares than what’s being offered at the major label level. Kendrick Lamar famously released what many consider to be his debut album, 2011’s Section.80, with Empire. Since then, acts ranging from Young Dolph to Fat Joe & Remy Ma have experienced chart success with albums released through the Bay Area-based company.

“They have the resources like a major, but they’re still giving you the majority of your money.” Kingston sings Empire’s praises, particularly that of its founder, Ghazi Shami, who started the company in 2010 and is known to be very hands-on with the artists he works with. “They’re showing you how to invest your money. They’re showing you how to really stay consistent and connected with your fans. You know, just really breaking it down.”

Kingston performing during the Music Choice Heads Back To School in New Orleans at the House of Blues, October 2013.. (Credit: Sean Gardner/Getty Images for Music Choice)


The question that many will ask, as Kingston reintegrates himself into the mainstream ranks, will be simple: with this much left in the tank, where’s he been all these years?

When posed with this question, Kingston answers unassumingly, almost as if it hadn’t really occurred to him that he’d ever been considered missing in action. To be fair, the details of his career suggest that details of his absence have been overexaggerated. Following the release of Back 2 Life, Kingston rarely went more than a full two years without at least some level of action, whether it was featuring beside Tyga, French Montana and Pusha T on Mally Mal’s 2014 “Wake Up In It” single, or releasing under the radar singles like “All I Got” in 2016 (which, to Kingston’s credit, does have a music video that’s been viewed a couple million times on YouTube). There was 2017’s “Holding Back” and a collaboration with still-relevant, multi-platinum recording artists Davido and Tory Lanez in 2019, “Peace of Mind,” that appears to have flown seriously under the radar. Last year brought about a collaboration with G-Herbo, and since then the focus has been Deliverance, and the road to it.

Kingston’s so-called disappearance, however, has more to do with the nature of it than its length. “Beautiful Girls” remains his biggest career success, but it certainly wasn’t the only one. The single that immediately followed, “Me Love,” enjoyed Top 15 success on the Billboard chart, peaking at no. 14, earning Kingston an early reputation as a hitmaker. 

Few things, if any at all, sounded like the music Kingston was pumping out—at the age of 16, no less. These were not Top 40-designed songs with the occasional Jamaican ad-lib, sprinkled in for “authenticity.” These were the pop dreams of a young man determined to bring the beauty of his heritage to the big stage. And they resonated with an audience wider than probably even he could have imagined at the time. “I had the time of my life,” he says about being a teenager experiencing that level of success his first go-round. “I was a young kid from Jamaica, where we grew up hard, you know? I used to have to walk to fetch my own water to take a shower. There was real stuff going on down there. Then I’m 15, going to L.A., getting a huge record deal with Epic Records. It was surreal.”

Kingston’s opening act was hardly over after “Me Love.” The third single from his debut album, “Take Me There,” brought Kingston back into the Top 10, at No. 7, making for quite the trilogy. Three singles, three Top 15 finishes on the Hot 100. A remarkable feat for any artist at any level, let alone someone who hadn’t yet reached voting age. The album’s fourth single, “There’s Nothin,” a collaboration with Paula DeAnda, enjoyed modest success, peaking at No. 60, but its modest performance mattered none to Kingston’s trajectory. By all indications, it was safe to consider Kingston a star in the making, and expect consistent chart performance for years to come.

Soulja Boy, Tammy Brook, Darly Murray, Janice Kingston, Sean Kingston, and Kanema Kingston serve Thanksgiving dinner on Skid Row on November 26, 2015 in Los Angeles. (Credit: Lilly Lawrence/Getty Images)


Despite a noteworthy sophomore campaign, things did not shake out that way for Sean Kingston. “Fire Burning,” the lead single from his second studio album, Tomorrow, peaked at No. 5, becoming his second biggest chart success, but the energy around the release and Tomorrow was not as fevered as it was during Kingston’s debut campaign. It’s expected that a teenager would experience growing pains while building a career, but Kingston notes that one of the pitfalls he endured were creative differences with Epic. “It was just the label kind of really just forcing me like, ‘Yo, yo, yo, yo like… We gotta get another album. We gotta do this. We gotta do that.” If Kingston is purposely trying to sound frantic and panicky, he’s doing a really good job. “It’s kind of like, I didn’t wanna be in a situation again where I didn’t have a lot of creative control.”

The banner event that most people, Kingston included, point to in discussing his perceived absence is the jet ski accident that made international headlines in 2011, and nearly claimed his life. According to reports, Kingston was throttling and turning the jet ski simultaneously (a discouraged practice) when he lost control of the vehicle and slammed into a bridge so hard, imprints of his body were etched into the side of it. 

“I’d torn my aorta,” he says. “Open heart surgery. When I was going through that, it was like, I’m not even thinking about music. You know what I’m saying? I had a tube down my throat.” 

One can only imagine the potential lasting mental effects of being involved in an incident that usually results in loss of life. Kingston makes it pretty clear that it affected him in ways that influenced his career, or at least his level of activity. “I’m not gonna lie, it held me back. Before the accident, I was on fire. And when [it] happened, I just fell back. Recovery mode had me out of the game for at least a year.” 

As Kingston prepares to make a return to the spotlight, he recalls an exchange he had with Swae Lee, one-half of the hitmaking duo Rae Sremmurd, who has also enjoyed considerable success on the solo circuit. One of those solo ventures, 2017’s “Unforgettable,” a French Montana song Lee’s chorus helped make ubiquitous—to the tune of a No. 3 peak on the Hot 100—was a highlight of American pop music’s mid-2010s welcoming of African and Caribbean influence to the mainstream. (Drake’s “One Dance” and “Controlla,” both released in 2015 and inspired by African and Caribbean music respectively, are the most popular examples.) 

“Swae Lee told me, ‘Sean, do you understand this? When I was writing ‘Unforgettable,’ you were the person that was in my mind’,” Kingston recalls. It says something, that at the height of Kingston’s supposed absence, he was influencing a burgeoning pop sensation from afar. (Lee had just topped the Billboard 100 as a member of Rae Sremmurd with “Black Beatles” in 2016, and he would repeat the feat as a solo artist in 2018 beside Post Malone on “Sunflower.”) Kingston certainly experienced feelings of helplessness watching others succeed with a formula he felt he was instrumental in pioneering. 

“Yes, that’s 100%,” he responds when asked about this. “It’s crazy, when I was working with Chris [Brown], he said, ‘It’s crazy. You started something and you were at the forefront… You’re not getting a lot of credit for it.’”

Still, “I wouldn’t regret anything, I wouldn’t change anything.” Kingston says. And at the ripe age of 31, there’s time for credit, and a whole lot more.

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