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With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. We’ve already named our Honorable Mentions and our No. 25 star, and now we remember the century in Ed Sheeran — who went from coffee shops to stadiums without ever changing his fundamental singer-songwriter identity.

A single person, playing the guitar alone on stage in the middle of a stadium. It’s a fantasy — being an artist whose music and lyrics are simply so undeniable, so unifying, that they leap from the meekest clubs to the most gargantuan venues in the world! — that countless singer-songwriters from all walks of life have attempted to strum into reality over the past 25 years, and almost every single one has come up short. It’s the wrong instrument for this century, really: modern pop does not function like it did back when rock ’n roll was the dominant sound, so this Greatest Pop Stars list does not include a slew of six-string-toting chart-toppers.

With that in mind, the scale of Ed Sheeran’s 21st century success is even more impressive. In a pop age where singer-songwriters generally bump against their commercial ceiling relatively early in their evolution, this red-headed kid from Halifax kept soaring higher and higher, eventually reaching a space where his longevity, global appeal, influence and multi-quadrant hits allowed him to stand alone. He used to be a teen busking on the streets of London; now, Sheeran often finds himself in the center of 80,000 people, an acoustic strapped to his shoulder, no one and nothing else in his vicinity. And considering everything he’s done, he doesn’t even look that out of place.

Unlike hitmakers such as John Mayer, Jason Mraz and Gavin DeGraw — singer-songwriters who burst onto the scene in the 2000s with flashy, radio-friendly pop singles — Sheeran began his journey into the spotlight with a quiet, unassuming breakthrough hit. Following years of independent releases in between street performances and open-mic nights across the U.K., Sheeran chose “The A Team,” a pleading folk ballad about a sex worker addicted to drugs, as his debut single in 2011 – betting on its juxtaposition of finger-picked melodies and a soothing vocal tone with dark subject matter and stripped-down production.

The bet paid off: In the heart of the EDM-fueled, turbo-pop assault at the top of the Billboard Hot 100, the minimalist sing-along of “The A Team” counteracted the spastic movement of concurrent megapop hits by LMFAO and Pitbull. There had been no shortage of hushed, bleeding-heart singer-songwriter fare that had found its way to adult pop listeners prior to “The A Team” taking off, but Sheeran’s debut was a touch smarter (“A Team” refers to the “Class A drugs” that the song’s subject has taken), more sincere (the way Sheeran warbles “She don’t wanna go-o-o-o outside, tonight” as a major emotional payoff), and altogether more striking than the soundalike songs around it, climbing to No. 3 in Sheeran’s native U.K. and to No. 16 on the Billboard Hot 100. 

Beyond its chart peaks, “The A Team” introduced Sheeran as an early-twenties troubadour worth investing in long-term. He played the song on late-night talk shows, and later at the Grammys, where it was nominated for song of the year. Sheeran’s debut studio album, +, arrived a few months later in 2011, scoring a respectable No. 5 debut on the Billboard 200. And while third single “Lego House” replicated the gentle guitar-pop formula of “The A Team” (with a Rupert Grint-starring music video, as a play on the Harry Potter actor’s physical resemblance to Sheeran), in between, “You Need Me, I Don’t Need You” shook up Sheeran’s image as a hip-hop-adjacent music industry shrug-off, with the singer-songwriter rapping over drum loops, guitar and piano. The song never reached the Hot 100, but became a live staple and fan favorite; more importantly, “You Need Me” expanded expectations for what an Ed Sheeran song could sound like as his voice was reaching wider audiences.

Soon enough, those wider audiences would include Taylor Swift — a country superstar yet to fully cross over to pop in the early 2010s. Swift tapped Sheeran for the Red duet “Everything Has Changed,” which became a top 40 Hot 100 hit as one of the album’s later singles, then brought him on the road as the opening act on the Red arena tour. Swift’s co-sign was and remains a crucial stamp of approval for aspiring artists, but she went above and beyond as an early Sheeran supporter; the two remain close friends and collaborators more than a decade later, having recently re-recorded “Everything Has Changed” for Swift’s mega-selling Red (Taylor’s Version).

By the time Sheeran’s stint on the Red Tour wrapped up in September 2013, he was a star in his own right, headlining Madison Square Garden for the first time that fall and picking up a best new artist Grammy nomination. The collaborators on his next album, 2014’s x, demonstrated the glow-up of the busker turned arena headliner: lead single “Sing” was produced by Pharrell Williams, working the same rhythmic magic that he applied to Justin Timberlake’s debut solo single “Like I Love You,” and follow-up single “Don’t” was helmed by the unlikely generation-separated super-producer duo of Rick Rubin and Benny Blanco.

To this end, x functioned exactly like its titular math symbol would suggest, taking Sheeran’s sonic blueprint and increasing its scope and sound: “Sing” was a rhythmic pop cut that brought Ed’s storytelling to the club for the first time, while “Don’t” was a jilted-lover lament (about a fling with a fellow pop star, rumored to be Ellie Goulding) that diced up sighing harmonies among rapped verses. Yet “Thinking Out Loud,” the blue-eyed soul romantic ballad, was bigger than either of them, heightening Sheeran’s earnestness and sentimentality to wedding first-dance proportions. “Thinking” reached No. 2 on the Hot 100, stuck for eight weeks behind Mark Ronson and Bruno Mars’ “Uptown Funk!” — but winning song of the year at the 2016 Grammys, after performing the song alongside John Mayer, Questlove and Herbie Hancock at the 2015 ceremony, made for a nice consolation prize.

As the wins kept accumulating for Sheeran in the mid-2010s, he started scoring hits that sounded like Ed Sheeran songs but came under the names of other artists. “Love Yourself,” an acoustic kiss-off performed by Justin Bieber, became a downtempo smash from his Purpose album by essentially replicating the Sheeran songwriting formula and serving it as a change-up from Bieber’s trop-pop hits “What Do You Mean” and “Sorry.” In the years leading up to “Love Yourself,” Sheeran also co-penned songs for artists like One Direction and Jessie Ware, but Bieber’s hit (which topped the Year-End Hot 100 in 2016) was an inflection point for the songwriting calls he started answering, and was followed by top 10 hits like Major Lazer’s “Cold Water,” Benny Blanco’s “Eastside” and Liam Payne’s “Strip That Down.” More often than that, the songs co-written by Sheeran smacked of his tone and melodic instincts, a superstar bending other perspectives and sounds toward his own.

Meanwhile, he also established himself as a must-see live performer. The x Tour was Sheeran’s first arena headlining trek, and he successfully translated his long-running stage setup — no backing band, no glitz or glamour, just a collection of pedal loops that allow him to re-create the sonic worlds of his songs on his own — for tens of thousands of ticket buyers. Whether perceived as a gimmick or an act of live-show wizardry, Sheeran’s touring approach gave him an identity in a crowded market as he accrued more hits to play for bigger audiences; no matter who else was out on the road, they weren’t going to put on a show quite like Ed’s.

If x was the album that elevated Sheeran to pop’s arena class, its follow-up, 2017’s ÷, was the project that made him a no-doubt superstar. That’s mostly thanks to “Shape of You,” the gargantuan lead single that will likely stand as the biggest hit of Sheeran’s career: a tropical house cocktail with a propulsive marimba line, playful falsetto and vocal chants that inject some drama into Sheeran’s tipsy flirtations, the song spent a whopping 12 weeks atop the Hot 100, gobbled up millions of radio spins and billions of streams, and finished 2017 as the biggest song of the year. If Sheeran’s career prior to that moment consisted of revving up his pop bonafides, “Shape of You” slammed down the gas, as a fully inescapable smash that is now officially one of the 10 biggest songs of the Hot 100 era.

Of course, the success of ÷ wasn’t limited to one song: “Castle on the Hill,” the racing rock single that Sheeran released on the same day as “Shape of You,” became a top 10 hit as well, and stands as one of his most emotionally resonant radio favorites. The Irish folk riff “Galway Girl” never reached the chart heights of its fellow singles on the track list, but quickly became a beloved fan track, and its streams have surpassed the 10-figure mark. And “Perfect,” another wedding-ready waltz in the mode of “Thinking Out Loud,” received a remix featuring none other than Beyoncé that December, which helped the single power to the top of the Hot 100. Toss in “End Game,” Swift’s Reputation track featuring Sheeran and Future, and Ed ended the biggest year of his career as an unquestioned A-lister, capable of leading hits on his own and holding his own alongside fellow superstars on blockbuster collaborations. (In 2019, Billboard named Sheeran the Greatest Pop Star of 2017.)

Topping that 2017 commercial apex was almost impossible to imagine — and to his credit, Sheeran didn’t really try to. His next full-length was 2019’s No. 6 Collaborations Project, a collection of household-name team-ups that was inspired by one of Sheeran’s pre-fame projects. The left turn tempered the sky-high commercial expectations of the proper ÷ follow-up, although “I Don’t Care,” the album’s dancehall-adjacent duet with Justin Bieber, still became one of the biggest pop hits of the year, reaching No. 2 on the Hot 100. Also featuring Travis Scott, Cardi B, Chris Stapleton and Bruno Mars, among many others, No. 6 became another No. 1 album for Sheeran, in the same month that his two-year-plus world tour in support of ÷ finally wrapped up, as the biggest of all time to that point; he largely took the next year off at the COVID-19 pandemic raged, and became a father in August 2020.

Sheeran’s next proper solo album, 2021’s =, powered him into his second decade as a star, with the singles “Bad Habits” and “Shivers” both riding uptempo pop productions and major hooks toward comfortable stays inside the top 10 of the Hot 100 chart. Swift appeared on a remix of the album’s “The Joker and the Queen,” and Lil Baby stopped by a new version of “2Step”; outside of =, Sheeran swung by a reworked version of “Peru,” from Nigerian star Fireboy DML, to notch another global hit that recalled some of the cross-genre pollination from No. 6 Collaborations Project. After that, a hard pivot: 2023’s – album marked a downbeat reflection on personal tragedies, including the death of Sheeran’s close friend and complications with his wife’s pregnancy, that was primarily produced by Aaron Dessner, who had helped Swift enter indie-folk terrain on Folklore and Evermore three years earlier. Both – and its surprise follow-up/counterpart, Autumn Variations, were too mournful to spawn any hit singles, as Sheeran seemingly issued both projects more for his own peace of mind than for radio gains.

But that’s the good thing about graduating to no-brainer stadium status: Sheeran can easily weather a commercial lull because he’s collected so many hits, and established his brand over the course of a decade-plus, while remaining a road warrior and onstage force. He’s been adjacent to the biggest artists of the 21st century while sneakily out-streaming a lot of them; just take a peek at Sheeran’s Spotify page, and try to count up how many of his songs have crossed the one billion mark. And while Ed has never been the toast of tastemakers, he has unquestionably written songs that are built to last — new wedding-reception staples and tried-and-true pop playlist mainstays — while also influencing the next generation of singer-songwriters, who have their sights set on the biggest crowds imaginable.

Ed Sheeran has transcended every pop trend, succeeded in a variety of styles, and made his voice a familiar sound in every context of modern pop music. He’s still enormous, and probably will be for a long, long time. Not bad for a guy with an acoustic guitar and loop pedal.

Read more about the Greatest Pop Stars of the 21st Century here and check back on Tuesday when our No. 23 artist is revealed!