Ed Sheeran Un-Zipped: On His Pharrell-Produced Single, Being a Sex Symbol and Turning Betrayal Into Song (Cover Story)

Ed Sheeran has found the perfect way to shield himself from fans: He is walking down lower Broadway carrying a load of five boxes he just picked up at New York’s most famous sneaker boutique. You can barely see his red hair peeking out over the top of this two-foot pile of footwear. Mind you, he didn’t buy the most expensive shoes Flight Club has to offer — those would be the Kanye West-designed Red Octobers, locked up in the store’s rarities cabinet with a resale value of $6,000 — only because Nike had already sent him a pair. He wore them when he accompanied Taylor Swift to the Vanity Fair Oscar party in March.

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“I like comfy shoes – the bigger ones that are squishier on the inside,” he explains, slightly muffled by an Adidas box obscuring his face. References are made to a pair of pointy leather shoes that he was talked into trying on the morning of the 2013 Grammys, when he was up for best new artist. Those respectable wingtips lasted about 10 seconds. But “my publicist basically has changed me from being the worst-dressed male of 2012 to looking presentable,” says Sheeran, which means he did let the label talk him out of wearing a hoodie with a tuxedo embroidered onto it to this year’s telecast. “I’m coming around to dressing a bit better. I’ve just never really given a f- about what people are wearing, so I don’t know why people care about what I have on.”

Back inside the SUV ferrying Sheeran around town, his publicist furtively tells someone back at label HQ that Sheeran has “done some damage” to Atlantic Records’ expense account. But they’re probably making it up in other departments, thanks to the 23-year-old Brit seemingly being one of the lowest-maintenance pop stars of all time. It’s not just his T-shirt-favoring look, which rivals the 1970s-era Eagles in making every night on the arena stage a Casual Friday. Whether playing clubs or stadiums, he has spent his entire touring career as a true solo act, alone onstage every night for up to an hour and 45 minutes. Watching him command audiences of screaming girls with not much more than an acoustic guitar, you could think of him as Llewyn Davis with a loop pedal and a severe case of overachievement.

Hear Ed Sheeran’s New Single, ‘Sing’

Now he’s about to throw everyone for another loop. Just when the pop world had gotten used to thinking of him as this generation’s James Taylor, he’s taking some musical cues from another JT. A Pharrell Williams-produced single, “Sing,” arrives April 7 to give Justin Timberlake a run for his money in the R&B-inspired falsetto department. The song is set to put the pop world on warning for an early-summer sophomore album that also reins in producers like Rick Rubin and Benny Blanco to help Sheeran run the gamut from neo-folkie to funkster and back again.

Sheeran has spent most of his career – which began when he released his first EP at 14 – in sensitive singer-songwriter mode, but his pop move is hardly without precedent. He has co-written songs for Swift and One Direction, and having both Swift and Harry Styles as VIP BFFs fascinated certain tender segments of the social media world before they ever heard a note of his own stuff. He also spent most of 2013 as Swift’s opening act on her Red Tour, which may have fooled a few people into thinking that he is, you know, an opening act. He’s not, though. As Sheeran will humbly remind you, he was able to sell out New York’s Radio City Music Hall before he ever tagged along with Swift, just on the basis of one freshman album and a curious, slow-evolving hit, “The A Team.” After his epic run with Swift wrapped up in September, he came back to New York to play three headlining shows at Madison Square Garden. How many people knew that selling out those shows – almost instantly – was a given?

“I’ve got to be honest: I did,” he says. “But no one else did. That’s why I made them hold three [dates],” even though the shows were announced one at a time. “I know my fan base and I can tell when something is going well. And record sales didn’t mirror ticket sales.” Sheeran says “+” — his major-label debut on Atlantic — has sold 4 million copies worldwide (“and Taylor sold 6 million of Red, so it didn’t fail in any sense”), but U.S. sales are 791,000, according to Nielsen SoundScan, not exactly the profile of an artist who can sell out Manhattan’s biggest venue not once, but three times over. “I’ve always sold more tickets in America than records. My income is 6 percent record sales. So live is kind of everything.” Atlantic might shudder to hear that but the label also benefits, thanks to the multi-revenue 360 deal they have in place with Sheeran. He grossed just over $8 million from headlining 31 shows in 2012. Plus, he’s probably one of the most profit-efficient performers in major touring right now. Where most acts selling out at the arena level require 10 trucks of equipment, he travels with five.

“His show is so captivating and so brave,” Swift tells Billboard, recalling their 66-gig North American stint. “It’s a really bold move to go out on [the Red] stadium tour with no band. It was just Ed up there with his guitar every night, doing what he’s done since he was playing in clubs and bars and pubs in England as a kid.” But she’s curious to see a change-up. “He plays solo acoustic now, but a few months ago we were in Germany and Ed came along to surprise the crowd with his song ‘I See Fire,’ which is a huge hit there. It was the first time he’d played with a full band, and I saw this spark in his eye. I have a feeling the production of his live show will expand over the next few years, and I can’t wait to see it every step of the way.”

A change is gonna come — but probably not in 2014. “Having a band as a singer-songwriter is a pretty standard thing, and I would lose my unique selling point once I’ve done that,” says Sheeran, noting that there are some points of pride about the current solo setup yet to be addressed. “No one’s taken that beyond a certain level, so to be able to do MSG with it was pretty special.” (So special that he got a new tattoo to commemorate the achievement – three boxing gloves on his right arm, honoring both his granddad’s days as a pugilist and the Garden’s days as boxing central.) “But I think once a large majority of people have seen me do it, then I’ll move on.” He pauses. “I want to headline a stadium,” solo, he announces. And this isn’t just a want – it’s happening. “I probably can’t say where, but we have booked one. And I think once I’ve done that, that’s me done on the loop pedal,” says pop music’s Great Red Hope.

The Subject Was Rosiness

In the back of the SUV, on the way to Tiffany’s, where Sheeran is set to pick up a watch – there are some limits to his anti-bling aesthetic – talk has turned to the fate of the red-haired in film, music and schoolyard humor. “The joke is, what is the one thing a ginger misses about partying?” asks Sheeran, as his manager waits in anticipation. A beat: “The invitation.” Groans notwithstanding, he keeps going. “Have you ever seen the Harry Potter films? They’re very unrealistic, and it’s not just about the wizards and the dragons. It’s that a ginger could ever have two friends.”

There is a point to this. “Gingers got properly sectioned [picked on] in schools,” says Sheeran. “It’s that racism is totally unacceptable in England, but you’ve got to take the piss out of someone. It’s all right. We will take over the world.” Sheeran takes his cue from Simply Red’s Mick Hucknall. “He had a good approach to it: ‘I might be ginger but I f-ed your mum.'”

NEXT PAGE: On His Justin Timberlake-Inspired Single

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He built up his redheaded ressentiment growing up in Suffolk, where his father was an art curator, his mother a publicist/jewelry designer and together they ran an art consultancy. He moved to London at 17, in 2008, where his independent approach to his music solidified.

“He turned up at the studio with a guitar on his back, when he was living on sofas,” says Jake Gosling, who produced almost all of Sheeran’s debut album and parts of the upcoming follow-up. “We found we had the same influences – [Bob] Dylan and Johnny Cash and Joni Mitchell and all that kind of stuff. Then he suddenly said, ‘I love rapping.’ But it wasn’t rap-rap, it was singing rap â?¦ He’d record an EP with me and then walk around after gigs and sell three or four, and it’d give him enough money to get some food and pay his bills a bit. He worked really hard for it. It didn’t fall in his lap.” In 2009, when Sheeran self-released his fourth EP, he played 312 gigs. By 2010, he decided to move to Los Angeles, where he played open-mic nights. And within a year he had a label deal.

“I did five EPs, all in different genres,” says Sheeran, “ending with a collaborations EP where I worked with all the underground rappers that I met. That last EP that I put out did close to 10,000 copies in week one, without a label. So by the time I signed to Atlantic, I had a fan base that was buying CDs and I had the radio expectancy.” Elton John’s Rocket Music Management snapped him up, too. His album debuted at No. 1 on the British chart, selling 102,000 copies its first week.

But while the single “The A Team” bowed at a lofty No. 3 in England, it had a rougher road on its way to the top 10 of multiple radio airplay charts in the United States. “They certainly win the longevity award” at Atlantic, says Tom Poleman, Clear Channel’s president of national programming. “Talk about sticking with a record for a long time. The first time I really got it, other than seeing Ed live, was when I went to my daughter’s camp and saw the kids all listening to ‘The A Team’ and realized there was something about this guy that had already started to seep into the teen world regardless of radio. Sometimes the consumers get it faster than the programmers. But I think what took him a year to achieve last time, he can probably achieve in a couple weeks this time.”

Says Atlantic chairman/COO Julie Greenwald, “‘The A Team’ was a challenging record for a lot of people, especially because of the lyrical content.” As in: It’s about a possibly dying prostitute, like so, so many freshman pop singles before it. “We said, ‘But look, this song is already a bona fide smash in every country but the United States, so it’s going to be a bona fide smash here, too.'” The single peaked at No. 16 on the Billboard Hot 100 and has sold 2.1 million copies, according to SoundScan. It helped that not everyone listened to the lyrics. “Not everyone gets that tune,” says Sheeran. “But rappers always did. Rappers f-ing love that tune.”

If he could go top 10 at the top 40, adult contemporary and rock formats in the United States with that bleak song, the reasoning went, imagine what he could do with something slightly more in radio’s pocket. He started writing for the new album three years ago, he says, before + even came out. The first song he came up with was “One,” which also happens to be the last song he wrote for Alice, the ex-girlfriend who was the subject of all of his debut album’s romantic songs. “One” takes his minimalist live approach to its furthest degree, putting your ear right next to his acoustic guitar strings as he bids farewell to his former muse. It’s an intimate moment, and transitional both lyrically and musically, as Sheeran then shifted from one extreme to another, setting out to work with Pharrell Williams, who at that point was only about the third-hottest driving force in popular music, as opposed to his pole position now.

“Sing,” the new single, represents the first time Sheeran has worked with a pre-existing track. And it almost didn’t happen. Williams recalls that when he played Sheeran a demo, “He was like, ‘Nah, I love it, but it’s not for me.’ And I said, ‘Just give me a shot. Pick up your guitar and strum along with it for a little bit, and see what happens.’ So after figuring out the chords that I had laid down, in between jokes and people coming in with coffee, he kept playing it, and he looked up at me, like, ‘Shit, is this really happening?’ as I’m looking at him with an ‘I told you so’ smile.” Thirty minutes later, the song was pretty much finished. “He’s one of the most impressive, underestimated singer-songwriters of our time. And now he’s got a dance record. I say ‘dance’ not because it’s electronica, but because it’s danceable. And he was able to still tell a really good story on top of it.”

Asked if he might have been unconsciously inspired by Timberlake on “Sing,” Sheeran proves willing to go beyond that: “It was pretty close to a direct inspiration,” he says. “I love Justified and FutureSex/LoveSounds, so I took inspiration from those.”

There is at least one other track on the new album that pursues a similarly groove-based R&B direction: “Don’t,” co-produced by the unlikely team of Rick Rubin and Benny Blanco. Until early March, this was slotted to be the first single, but a chorus hinged on the lyric “Don’t f- with my love” may have prompted a desire to give Sheeran’s newest and youngest fans something a bit less provocative first.

There’s a story behind the historic summit meeting suggested by the production credits of “Don’t.” “I did it with Benny and I loved it; I tried it again live with Rick and loved it,” recalls Sheeran of his indecisiveness.

Sheeran first cut “Don’t” with Blanco, who has worked on hits from Katy Perry and Maroon 5. But then he tried it again with Rubin, known for his naturalistic, classic-rock approach. “I loved elements of both,” says Sheeran, “and I knew that together they could make something really super-powered, between Benny’s pop sensibility and Rick’s raw, earthy, gravelly coolness. So Benny went to L.A. and sat with Rick.” Offers Blanco: ” ‘Don’t’ is so f-ing raw, right to the chest and a jab in the stomach.”

It’s certainly Sheeran’s most provocatively confessional song to date. “The last album was more young and dewy-eyed and innocent,” he says. “I’ve still got very nice songs on this record. But some of them are bite-y. The story in ‘Don’t’ is 100 percent true. I could have gotten nastier – there was more shit that I didn’t put in. I was seeing someone for a bit of time, and then they ended up physically involved with one of my friends in the same hotel that we were staying in, while I was downstairs. And I feel like: Treat people how you want to be treated.”

“He has heartbreaks, as we all do, and he puts it down and he mentions people’s names,” says Snow Patrol’s Johnny McDaid, who’s a co-writer and producer on the new album. (The pair roomed together for most of 2013 in Nashville to work on songs, when Sheeran wasn’t away on the Swift tour, and the friendship has worked out pretty well for McDaid – when the recording sessions moved to L.A., Sheeran introduced him to Courteney Cox, who’s now McDaid’s girlfriend.) “The first song we wrote together was ‘Nina,’ a love song about heartbreak, both self-inflicted and otherwise, where he basically calls someone up and advises her not to be with him. That sort of self-deprecating diary is pretty honest. Most people are fearful of being naked in front of the world, and afraid to expose their weaknesses. Ed isn’t.”

But “Don’t” isn’t a self-deprecating diary entry; it’s an indictment. “I never saw him as a threat/Till you disappeared with him to have sex,” goes one lyric. “If I show courtesy and respect to someone, I expect to receive it,” says Sheeran. “When we’re in the same hotel, and I’m downstairs at my party and you’re upstairs doing that, that’s disrespectful.”

There’s a British emphasis on manners that infuses Sheeran’s statement of sexual betrayal. But he adds: “If you date a songwriter, be prepared to have songs written about you. If you do nice things, you’ll have nice songs. And if you do f-ed-up things, you’ll get a horrible song.” Translate that sentiment into an American accent, and he suddenly sounds a lot like Swift, a fellow member of pop stardom’s Candor Faction.

Rubin was impressed less by Sheeran’s Swift connection than the Nina Simone connection. “The thing that really surprised me was going to see him, seeing who his audience was,” says Rubin, “and then seeing him do a Nina Simone cover in the show — and seeing 12-year-old girls screaming their heads off for a Nina Simone song.”

For all the attention that R&B songs on the upcoming album will get, there’s still plenty of trademark acoustic strumming at its core, including one of the tracks that Rubin worked on. “Ed played me a lot of the demos or other tracks he had done with other people,” says Rubin. “Some of them worked really well, and some of them â?¦ Ed is not a pop artist who’s singing on tracks, you know? And some of the songs, what’s good about Ed didn’t come through. And then as soon as he played them on the guitar, it was like, ‘That’s incredible!'” That Rubin-Sheeran collaboration wrapped up the project, and the producer characterizes the session as “solo Ed performances, even though they sound like total records, in the same way that when you see him live, it doesn’t sound like he’s missing a band. They sound full and rockin’.”

If there’s a contradiction – the stripped-down solo songs that rock like band tracks – it’s one that Sheeran reconciles simply by not recognizing. That’s his way: He’s the scruffy guy who doesn’t care what he wears, but turns up on the red carpet of the Vanity Fair Oscar party; the open-mic songwriter who has come up with the biggest hooker-themed radio hit since Sting sang about Roxanne. And, let’s face it, being the only guy onstage is a smart business.

The biggest inherent contradiction of all may be Sheeran’s status as Britain’s least glamorous heartthrob. He recently came in at No. 2 in a British poll devoted to readers’ favorite “weird crushes.” “I don’t see myself as a sex symbol, but if other people do, I’m not going to complain,” he says. Nonetheless, the new song “Take It Back” has him proclaiming, “I’m a singer that you never want to see shirtless.” Is he sure about that? “No one does! I haven’t got a six-pack or pecs.” He may get some cards and letters begging to differ. “To each their own,” he shrugs.