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Ed Sheeran: Up All Night With Pop’s Hardcore Troubadour

The singer-songwriter used to be a misfit; now he’s a hard-drinking superstar. But what he really wants is a normal life.

‘Let’s go to my place for the finale!” Ed Sheeran shouts as he hops into an SUV. It’s just after midnight in London. Sheeran spent much of the evening in a bar, but even with his bright-red hair hidden under a ball cap, people started to recognise him. The DJ played one of his songs, and his friends had to create a wall around him so he could drink in peace. It all made him a little anxious, which is why we’re speeding to his West London home to keep the party going. 

Sheeran is celebrating tonight because he knows he’s about to score his first Number One hit in America with “Shape of You,” a sleek, funky stomper from his new album, ÷ (pronounced Divide). We’re joined by his girlfriend, Cherry, and his old friends Zack, Nathan and Catherine, who have been watching him perform since he released his first album, The Spinning Man, when he was 13. “I went plywood,” Sheeran, now 25, jokes about that LP. “Not gold. I sold 100 copies.”

Sheeran has been going hard tonight: espresso martinis and rum-punch shots at dinner, gin and tonics at the bar. It’s my birthday, and at one point he grabs my phone, takes a selfie of us and posts to my Instagram, writing “It’s my birthday bitches #london #hashtag #believe #achieve #inspiration.” He encourages friends to knock back pints with a drinking song that ends “Na na na na/Hey hey hey/You’re a cunt!”

Soon, we arrive at his house, a five-floor, industrial-style space with brick walls, wood floors and several personal touches: a Charmander Pokémon stuffed animal in his bedroom and a bong shaped like Benny Blanco’s head in the living room. There’s also a recording studio, a gym and a full bar, where he recently entertained several young cast members of his favorite show, Game of Thrones. As we arrive, Sheeran offers bedrooms to anyone who wants to “get rowdy,” then goes to work mixing drinks.

Watch outtakes from Ed Sheeran’s ‘Rolling Stone’ cover shoot:

With the possible exception of Justin Bieber, Sheeran is the biggest male pop star alive. But pop-machine refinement is something he resists full force. His life is a chaotic blur of too much pub food, 3 a.m. pool games, shots at dinner and impulsive decisions: “If you ever need a wedding band…” he says shortly after we meet and he learns I have a girlfriend. “I always say, ‘It’s free if I’m free.’ As long as you sort me out with a lot of booze and a bed, I’m there.” (During our time together, I will meet at least three friends whose weddings he has played.) He is filterless. “Powerful shit upstairs, man. Who did that?” he asks after emerging from the bathroom tonight, until a friend cops to it.

As his fame increases, holding on to a semblance of normalcy is important for Sheeran. He’s been hanging out with old friends a lot; he even wrote about them in his new single “Castle on the Hill,” a tribute to their rebellious high school days in Suffolk, England.

Around 4 a.m., Sheeran runs upstairs to grab his guitar and then takes a seat at the kitchen table. He proceeds to play for two hours straight – a gig considerably more intimate than the stadium shows he plays all by himself, backed only with an acoustic guitar and a loop pedal. Tonight he plays songs from ÷, as well as several unreleased tunes he says are planned for future albums. He takes requests, too – including “Love Yourself,” the Number One hit he wrote with Justin Bieber. “You know ‘Love Yourself’ is originally ‘Fuck Yourself,’ right?” he jokes before playing that version.

This is Sheeran’s gift in a nutshell: He’s a mix of old-school troubadour and Top 40 technician, a guy who could kill it at a coffeehouse open-mic night but is also one of the most pop-savvy songwriters alive. (He also raps surprisingly well.) His crowds are mostly teenage girls, but Sheeran is craftsman enough to impress someone like Elton John, who signed him to his management company in 2011. “He can write melodies so simply,” says Elton, who points to “Thinking Out Loud,” which won a Grammy in 2016 for Song of the Year. “Van Morrison would have been very proud to write that. He reminds me of me when I first came to America, in 1970. It was all systems go. Nothing was impossible. The unfortunate thing is, now, everyone sounds like Ed Sheeran: Shawn Mendes, Justin Bieber. …”

“Sorry, I’m a bit drunk,” Sheeran says after flubbing a line to a new track. He stops to roll a cigarette and heat up a pizza. Then he sits down and plays “Perfect,” a fingerpicked waltz from ÷. Like most of songs he writes these days, it’s about Cherry, whom he’s known since high school and reconnected with at an after-show party in New York. They kept their relationship secret for a full year, until Taylor Swift invited them to her Fourth of July party in Rhode Island and a friend Instagrammed a picture of a banner celebrating their one-year anniversary.

“I found a love to carry more than just my secrets,” Sheeran sings. “I don’t deserve this, darling, you look perfect tonight.”

“My tear glands are just throbbing,” says Catherine.

“Let me think of another tear-jerker,” Sheeran says.

“Please don’t!” she says.

He gets up and makes another gin and tonic. “Everyone cool? I am very cool.”

Around six, it’s time for bed.

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From left, with girlfriend Cherry attending a Mets game. “She’s the one person that’s going to remain constant for me,” he says. Credit: INFphoto.com; Sheeran busking in Galway, Ireland, in 2005, age 14. Credit: John Sheeran

Early last year, Sheeran and Cherry were touring a volcano in Iceland, when Sheeran ignored a guide’s directions to not stray from a path. As he approached a bubbling geyser, the thin crust of earth started to collapse beneath him, sending both feet into nearly 200-degree water. It was the first time Cherry had heard him scream. She ripped one of his socks off, taking his skin with it. “I still have post-traumatic stress over it,” she says. He had to be airlifted to a hospital. 

The couple could have headed home – instead, they pushed on with a trip that lasted six months. Sheeran, it turned out, really needed to get away from being a pop star for a while.

Sheeran’s default mood is relentlessly upbeat. But he admits that every now and then he “spirals.” This happened in 2013, when he scored an opening gig for Taylor Swift and moved to Nashville, where the tour was based. “I was on the most amazing fucking tour in the world,” he says. “I was just living in a country that I didn’t belong in, in a town I didn’t really know anyone.”

He began to drink – a lot. His frequent songwriting partner Johnny McDaid was worried about Sheeran when he saw him at a show in Hollywood in 2015. “He was just go, go, go,” McDaid says. “I sat him down and said, ‘Look, man, please have all the fun in the world. But be careful because if that elastic snaps, it could take a long time to recover from it.’ ”

A single Twitter comment could ruin his day: “Everyone online was saying, ‘Ed’s going bald.’ And I’m not. But I convinced myself that I was. Ginger hair is just very fair – my hair is completely fine. I was also quite big at the time,” he adds, referring to his weight, “so I kind of got a complex about two things I would have never given a fuck about.”

He also lost some friends. “The Forbes list actually fucked it up,” he says, referring to a report in the magazine indicating he made $57 million in 2015. “I was getting texts from people with pictures of cars going, ‘I’d like this for my birthday, please. This one’s only .06 percent of your annual income.'” (He ended up ditching his phone; he uses an iPad to communicate and a flip phone for close family.)

So after attending the Grammys last year and winning Song of the Year, Sheeran skipped the afterparties and boarded a plane to Iceland. Once his foot had healed, the couple traveled around rural Japan for a month, from Hokkaido to Okinawa, where he was able to walk around in anonymity, “eat weird food, soak in the hot springs and ski.”

Sheeran stopped smoking and cut way back on drinking. In June, he spent three weeks in Ghana at the invitation of Ghanaian-English singer Fuse ODG. Working in Fuse’s house, he started writing African-influenced music. “Anytime we made a song, they would throw a party for the song,” he says. “He would invite 200-plus people ’round, and we would just party to that song until the early hours.”

Only one of those songs, “Bibia Be Ye Ye,” appears on ÷, but the freedom Sheeran felt on his journey lingered. While Sheeran’s last album, x, featured bitter takedowns of exes, ÷ has songs like “Happier,” which he wrote after a wedding, when he ran into his ex and her boyfriend, whom Sheeran had always held a grudge against. “He was really sound,” says Sheeran. “I thought, ‘Of course, this is what’s meant to happen.'”

Elton says Sheeran’s travels “refreshed his soul.” “I’ve noticed, in the last few months, he knows it’s going to be all right,” says McDaid. “He knows that he’s done a pretty amazing thing again. I think he reconnected to his friends and family, and he feels anchored.”

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“I love his values – he’s naughty as well,” says Elton. Credit: Michael Kovac/Getty

It’s 11 the morning after Sheeran’s impromptu living-room concert. Rain patters on the windows of his guest room, revealing a gray sky. Only five hours have passed since he called it a night, but he can be found downstairs in his gym, shirtless, in the middle of his daily 10-minute elliptical workout. “Just sweating it out!” he says.

His studio is across the hallway. Sheeran asks everyone who visits to sign its walls. Signatures include Rick Rubin, Harry Styles and Benny Blanco, and a drawing by Damien Hirst, one of his favorite artists. One wall is bare, except for a single name. “That’s Clapton,” says Sheeran with a grin. “Elton’s coming next week and Cherry’s cooking, so I’m going to do a legends wall.”

Sheeran and Clapton first started talking over e-mail. Clapton invited him onstage in Japan last year and sometimes comes over for dinner. Sheeran isn’t a favorite with critics, but, he says, “I could give a fuck about what people think. Anytime anyone has a problem with me, I’m just like, ‘My heroes like me. The people I started music for are fans of my music. So why the fuck would I care about what anyone else thinks?’ ”

We head to lunch at a nearby pub, where Sheeran promptly orders a round of his hometown ale Adnams: “I love drinking really thick ale in January.” He talks about growing up in Suffolk, where he was made fun of for being bad at sports, for his red hair – and, most of all, for his stutter: “You’d put your hand up and not be able to speak. And kids are cruel. So once that would happen, someone would imitate it. And then you’d be like, ‘I’m not going to put my hand up next time.’ ” He credits rapping along with Eminem’s Marshall Mathers LP for helping him lose the stammer.

His parents were curators for art galleries, putting together exhibitions and lecturing around town. His dad taught him to be tough. “He grew up with a harelip,” he says. “And he said, ‘Anytime anyone picks on you, hit him as hard as you can and they will never rip into you again.’ ” His father still doesn’t take any shit: Sheeran tells a story about him lighting a cigarette at a recent Warner Bros. party. “Someone said, ‘Sir, you can’t smoke here.’ And he said, ‘I am Mr. Warner,’ and they left him alone.” His mom is the opposite. “She is literally an angel,” says Sheeran.

Though his dad suggested fighting to deal with his problems, Sheeran preferred humor. “Most ginger-haired people I know are very outgoing and comedic,” he says. “They basically say the joke before you can. Like, my first album is orange. There’s a reason it’s orange – I’m getting there before you can.” He thinks those days have a lot to do with his career choice: “The whole musician thing kind of comes from wanting to be loved and wanting to be liked.”

Sheeran dropped out of school in 2007, when he was 16, and moved to London. He started performing, striking out at guitar open mics but finding an audience at hip-hop clubs, comedy shows and jazz open mics. “Anywhere it’s not the norm to have a singer-songwriter be there, I instantly stood out,” he recalls.

“He can write melodies so simply,” says Elton. “He reminds me of me when I first came to America in 1970. It was all systems go. Nothing was impossible.”

In 2010, Ben Cook, the head of Asylum Records, saw a clip of Sheeran online. Cook went to check out several shows – including one in Southampton, England, where Sheeran stood on a chair in the middle of the audience and played unplugged. “He was rapping,” Cook says, “so the guys were trying to keep up with him, and then there was the really romantic stuff the girls were responding to.” Cook signed him soon after.

Sheeran’s first big U.S. tour was supporting Snow Patrol in 2012, around the time his first single, “The A Team” – a ballad about a crack-addicted prostitute he met at a homeless shelter – was blowing up. “In Orlando, there were, like, 200 people in the front row to see Ed,” says McDaid, Snow Patrol’s guitarist. “By the middle of the tour, there were about 2,000. You could see it happening in front of you.”

His next tour was considerably bigger: a 66-date run opening for Swift. “I heard his song ‘Lego House’ in Australia when I was on the Speak Now tour,” says Swift. “It just cut through everything else.” Their managers put them together, and they ended up sitting on a trampoline in Swift’s backyard and writing “Everything Has Changed.” Each night, Swift invited Sheeran onstage to play the ballad.

Offstage, this was his most romantically prolific period. He says he hooked up with some of Swift’s famous friends. “Taylor’s world is celebrity,” says Sheeran. “I was this 22-year-old awkward British kid going on tour with the biggest artist in America, who has all these famous mates. It was very easy. … I would often find myself in situations just kind of waking up and looking over and being like, ‘How the fuck did that happen?’ ” (Katy Perry recently summed up his appeal as a secret ladies’ man: “Everybody loves him, no one’s scared of him, they want to date him. They can have him.”)

Sheeran chronicled some of these relationships on his second album, 2014’s x. He wrote “Don’t” about a fling with a fellow pop star that ends when he learns she’s had sex with a friend who was staying on the same hotel floor. Many speculated it was Ellie Goulding, who afterward released “On My Mind,” which included the burn “You wanted my heart, but I just liked your tattoos.” Goulding has denied having ever been involved with Sheeran.

One person he did not date on the tour was Swift, despite TMZ headlines. “I found that aspect quite lazy journalism,” he says. “There wasn’t any truth to it whatsoever.”

Sheeran and Swift see each other only once or twice a year, but they still feel close to each other. “We’ve gotten matching Scottish folds, made each other arts and crafts Christmas presents, vacationed with our families, and had each other’s backs,” says Swift. “He is the James Taylor to my Carole King and I can’t imagine a time when he wouldn’t be.” He imagines them doing a stadium tour where they trade songs for an evening, much like the one Jay Z and Justin Timberlake did a few years ago. “She would be there if everything ended for me,” Sheeran says. “Taylor is kind of an anomaly in that sense.” He’s been annoyed at the backlash against her lately: “She’s omnipresent because she’s the most famous woman in the world, so she can’t make the decision to not be in the press. I always stick up for Taylor.”

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“He is the James Taylor to my Carole King,” says Taylor Swift. Credit: Kevin Mazur/Getty.

Most weekends when he’s not on tour, you can find Sheeran watching field hockey. Cherry played for Duke until 2014. She moved to London last year with Sheeran, and signed a contract to play for Wimbledon Hockey Club (field hockey is a big deal in England). During the week, she works as a financial consultant. “She’s the nicest girl you’ll ever meet, but on the field she’s a fucking animal,” he says proudly.

At Oxford Hawks Hockey Club one Saturday, Sheeran takes his spot against a fence to watch the first game of the season, chatting with a few parents. (“Are you up to anything musical?” one asks.)

Cherry, number 17, rushes over to him, and they kiss, and do their sort of secret handshake. For their first date, he took her to see him accept an award at an American Institute for Stuttering gala – “It was quite an upsetting event,” Sheeran says, “because there are lots of kids that just can’t get their words out.” The second date was a birthday party for Adele’s manager. Sheeran “tested” Cherry by leaving her alone for a few hours. “One of the main points of being in a relationship with me,” he says, “you have to be really fucking sociable and good at talking to people, because I will be dragged away loads at parties and events. And Cherry’s perfect at it. She makes friends with everyone.”

After the match, Sheeran is driven to the team clubhouse. He grabs a tray and fixes himself a potato with beans and cheese, giving a big thumbs-up as he chews. He’s about halfway done when several more teams pour into the room: high school girls. Several cliques of them inch toward his table. The whole room seems to be wondering why, exactly, Ed Sheeran is here. “I’m gonna need to get out of here,” he says. “I’m getting filmed a lot.” He pulls his cap down and walks out, head down, and makes his way out unscathed. “I just realised that was an entire school – all the sports teams,” Sheeran says back in the car. “Not ideal.”

This kind of attention freaks Sheeran out a little, and lately he’s been dealing with even weirder invasions of his privacy. Not long ago, a police officer pulled him over and asked for a selfie. Sheeran recently found a drone in his garden. He’s “100 percent” sure that someone on his 40-person team is selling information to the press. “I just want to know who it is,” he says. The worst part is getting stared at: “People film on the sly – I get really fucking anxious.” And one way he deals with that anxiety is drinking.

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Freestyling with Rita Ora at the BRITs in 2015. “I wasn’t in the best frame of mind that night,” he says. Credit: Paul Hampartsoumia/REX

“Do you have any white tequila?” Sheeran asks a waiter at a New York restaurant. “Not Patrón, though.” Yes, they do. “Five shots of that, and one shot of passion-fruit juice, please. Put the tequila on ice, and then let it sit for a bit. And then pour it over ice into the juice, then shake it.” The waiter at New York’s ABC Kitchen gets on the case: They do not carry passion-fruit juice, but a store nearby does have it, and someone has been sent out.

Since I saw him in London three weeks ago, Sheeran has been on a promo tour, visiting England, Norway, Germany, France, Asia and Australia, where he stayed at Russell Crowe’s house. “He has his own pub,” Sheeran says. “I was so fucking off my chops, and I didn’t realize he’d drank a bottle of gin and was off his chops as well.” There was a minor crisis around 8 a.m., when everyone realized Sheeran had wandered off to bed and ended up in a grassy area riddled with deadly snakes. Cherry feared another Iceland-like debacle. “He was stumbling into the grass, falling into the bushes,” she says.

Sheeran escaped unharmed, but there are a lot of stories like this. In Nashville, in 2013, he was pretending to play drums with two beer bottles at 4 a.m., the night before an arena gig. He struck the table and ended up with a big piece of glass inside his right hand. He missed a nerve by a millimeter.

Then there’s the scar. Sheeran was recently attending a party thrown by Princess Beatrice at the Royal Lodge, near Windsor Castle, when he started messing around with ceremonial swords. The story changes often – some say it was Beatrice herself; Sheeran says it was singer James Blunt – but someone slashed Sheeran’s right cheek. “He went to the hospital and came back ready to party with stitches on,” says a friend. “And everyone was asleep. He was like, ‘What the fuck? I bled for this party and you’re all asleep?'”

“He can be extremely naughty. It’s a good thing he didn’t appear in the same era as I did, otherwise we’d be up for three weeks together,” says Elton, who has been sober for almost 30 years. “He’s not a big druggy, but he likes a drink. He’s a lot of fun.”

The five-shot tequila drinks arrive. Sheeran gulps one down and requests another. He talks about going to Tokyo, where he met up with Bieber. They did karaoke and shot pool in a dive bar. “He’s in a very good place – very sober, very present,” Sheeran says. “There’s been a 180 that’s happened, and there’s no diva behavior whatsoever. It really suits him.”

Does Sheeran think he drinks too much? “Often, I’m like, ‘Is it bad that I drink almost every single day?’ And then I look at my friends and most of them do the same. And they’re actually worse than me. The first thing Americans say is, ‘There’s a problem, and you need to go to rehab.’ But I don’t wake up and drink. I don’t depend on drink. I can go without it completely. I just enjoy going out and having fun, being 25. And I think that’s a normal thing.”

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After joining the Stones onstage in 2015. Courtesy of Ed Sheeran

In his dressing room at Saturday Night Live two days later, Sheeran looks over the walls of the greenroom, which are full of pictures of past musical guests: Kanye West, Paul McCartney, Sheeran himself. “I look like a fucking gimp,” he says, remarking on a press shot where he’s leaning forward with a serious face. Soon, a live feed of the show’s dress rehearsal comes on. He cackles at Melissa McCarthy’s Sean Spicer impression – “Fucking hell!” he says – and host Alec Baldwin’s monologue.

He talks about the future. He’s in the process of auditioning members of a boy band he’s creating. He’s already written lots of songs for the group – “really, really decent. Superpop, but obviously credible. I’m gonna put three or four boys together and do all the songs, take them on the stadium tour with me.”

Sheeran’s ÷ tour will take him across the world – arenas this year, stadiums next year – before wrapping up by early 2019. He’s edging toward his ultimate goal: “I want to do stadiums everywhere,” he says. “Like George Strait’s level – he tours every four years, does a couple of stadiums and then fucks off again.” Sheeran also plans to star in a low-budget film, like Once, featuring his own acoustic soundtrack. “I want to have one in my career,” he says.

He’s showing a member of his team the “cash me outside” meme when his pal Zach Braff blasts into the greenroom, along with his date. “There’s nothing more fun than being at SNL – I’m so geeked out,” he tells Sheeran. “This is like you at a Star Wars convention.”

Sheeran starts busting his balls, pointing at Braff’s backstage pass: “Why does it have that on it, though – ‘Talent’?”

“You motherfucker,” Braff says. “You’re supposed to be my wingman.”

Sheeran heads straight from the greenroom to the stage to perform “Shape of You,” not bothering to do any sort of vocal warm-ups. Later, he’s on his way to do his second song, “Castle on the Hill,” when he and Cherry run into Tracy Morgan. The comedian steers the conversation from The Empire Strikes Back to The Godfather to Michael Jackson. “Michael was music,” Morgan says. “With every fiber of his fuckin’ soul. The problem with Michael was that he peaked too soon. Listen to ‘ABC.’ He was eight years old when he did that! And once you peak, there’s nowhere to go.”

“You’re scaring me!” Sheeran says with a laugh. Morgan replies that Sheeran has nothing to worry about: “He’s good. He’s grounded. He’s got a woman right there. He’s gonna have a wife and family, and he’s gonna be fucking happy.”

The scene becomes more surreal when Baldwin approaches them in full Trump getup. All week, Sheeran has been admiring Baldwin’s two babies. “Whenever anyone brings babies around, I’m like, ‘We gotta get on that,’ ” says Sheeran.

After the show, Sheeran has to catch a plane to make a 9 a.m. soundcheck for the Grammys. “You’ll be fine,” says Morgan. “Get some sleep on the jet.” Baldwin asks about his tour plans: “Whatever you do, you’re young, you’re so talented. You guys are gonna have a baby. Just have it on your private plane.”

“Tour-bus babies!” says Cherry.

What Sheeran is really looking forward to is his 26th birthday next week, which he and Cherry will spend in the Austrian Alps. “It’s awesome meeting famous people,” Sheeran says. “But that’s not life. That’s not reality. One day this will fucking end. And I know the one person that’s going to remain constant is Cherry. I should just enjoy this while it’s there, but not let it become my reality. Because that’s not the reality I want to live in.”

From issue #786 (May 2017), available now.