Not that he has anything to worry about right now. He’s landed three Number One albums and has 95 arenas booked next year, with stadiums up next on the horizon. His calling cards are catchy, well-crafted pop-rock hits like 2015’s “Stitches” and 2016’s “Treat You Better,” where he comes across as an earnest guy who wants more than a fling, the type who’ll fly to Japan to convince you he deserves a shot.
Still, keeping his cool as he tries to build the long-term career of a Sheeran or a Taylor Swift is a lot of pressure for someone barely out of his teens. He takes comfort in the strict set of rules he’s developed to keep himself on track. Rule one: Hit the gym every single day. Rule two: Two vocal lessons per day. Rule three: Never say no to a selfie. This means that every hotel he stays at becomes a de facto meet-and-greet, with anywhere from a few fans to several thousand lining up outside.
When he walks out of the lobby of the Tivoli Hotel in Lagoa, Portugal, there are already a few dozen girls waiting by the entrance. “Hold on,” Mendes tells his team. “I gotta take some photos.” After a minute or two of efficient chitchat — “You’re amazing!” he tells one fan before his security guard whisks him away — he makes his way to the van. His two managers are in swimsuits, but he’s in skinny jeans and boots, his hair perfectly tousled for tonight’s festival gig. “Do you wanna sit in the middle?” he asks me. “Nah, I’m kidding. I’ll squeeze.”
His dad, Manny Mendes, takes the front seat and starts conversing with the driver in Portuguese. Manny, 44, has gelled hair, a goatee, shades and a polo shirt; Mendes’ team half-jokingly calls him “the real rock star” in the family. Back in Ontario, he owns a bar and restaurant-supply company, but his family is here in Portugal, where he spent his early twenties working in the restaurant we’re headed to now, owned by a cousin.
The Mendes family — Manny; his wife, Karen; Shawn and his younger sister, Aaliyah — last visited the country six years ago. “We rented a van,” Manny says. “We used to get it stuck everywhere because the goddamn streets were so small.” Something else happened on that trip: When they were shopping one day in the city square, Shawn hopped up next to a statue of a king and sang in public for the first time.
“I was just really weirdly inspired,” Shawn says. “They went into a store, and I remember my heart beating at a million miles an hour.” The song was Bruno Mars’ “Grenade.” He starts belting the lyrics: “Easy come, easy go!”
As we arrive at the nearby beach town of Lagos, Manny points out the dirt road leading to his grandmother’s house, where he spent summers as a child. He’s talking about the medieval city walls built to keep out pirates when Shawn’s eyes wander elsewhere: Three girls in bikinis are walking up from the beach. “There’s definitely some cuties here,” Shawn says. Just don’t expect him to talk to them. “Dude, I have no game,” he adds.
Manny says he was the same when he was younger, and suggests that the Mendes family’s good looks actually work against them in this regard.
“There’s less we have to do because of the good hair,” Shawn agrees. “We’re already 10 steps ahead. But being good-looking doesn’t make you have game.”
Justin Stirling, his 25-year-old head of marketing, speaks up. “All Shawn has to do is open up his Instagram DMs, see all the blue check marks and choose,” he says. “But it doesn’t happen often.”
“One day, brother,” Shawn says. “Maybe now that I’m 20. I said ‘fuck’ onstage the other day. That was a big day. I immediately felt bad about it.”
We roll up to Café Do Mar, a picturesque spot overlooking a shoreline full of sailboats, where a large group of Mendes relatives — all tan and super-friendly, just like Shawn — are waiting for his arrival. After exchanging hugs and hellos, he finds a seat at a side table for our interview. I ask if he would rather catch up with his great-aunt and uncle, but he says it’s fine: “They don’t speak English, so it would be very hard.”
Mendes orders chicken and tells me that he spent this morning doing his best to relax: He went to the gym, laid out in the sun and listened to some “soft-pop hits” on Spotify. Then he says something a little more surprising. A few days ago, he was in Amsterdam with some of his high school friends to celebrate his 20th birthday. He didn’t get to party as hard as they did, because he needed to watch out for his voice, but they did spend hours exploring the canals in a rented boat and checking out the city’s famous coffee shops.
“I love weed,” he tells me with a grin. “I wouldn’t tweet that — not yet, at least — but it’s really good for me. When I’m home, I’ll smoke and then play guitar for seven hours.” (He also saw shrooms for sale in Amsterdam, but opted not to try them. “I want to so badly,” he says. “I think it would help me a lot.”)
So far, Mendes has held on to his squeaky-clean image, staying far from tabloid controversy, but that’s beginning to change. Earlier this year, he and Hailey Baldwin made headlines when they showed up together at the Met Gala ball, holding hands as the cameras flashed. Though they told everyone on the red carpet they were just friends, that didn’t quite add up with the photos that emerged of them hugging in a park near Mendes’ home in Toronto. He acknowledges they were more than friends, but he’s still reluctant to call it a relationship: “I don’t even wanna put a title on it. I think it was more of a zone of limbo.”
But just a month after their Met Gala date, Baldwin was engaged to Bieber, whom she’d dated before. She immediately unfollowed Mendes on Instagram, and to make things worse, Bieber appeared to take shots at Mendes on a Top 10 hit with DJ Khaled: “It ain’t that hard to choose/Him or me, be for real, baby, it’s a no-brainer.”
Some on social media painted Mendes as a chump who got played by Baldwin, but he swears he’s not holding a grudge. “I get it, you know,” he tells me. “I texted Hailey, ‘Congratulations,’ and I really am happy for them. She’s still one of the fucking coolest people ever — she’s not just a beautiful person visually, but she’s one of the most beautiful hearts I’ve ever met.” It seems like he might be about to say something more about how it all went down, but he stops himself. “I think I’m an idiot to not, you know. . . . But you can’t control your heart.”
Mendes admits that the attention on his personal life has caused him a lot of stress. “I’d like to say I don’t care about it, but that’s not true,” he says. This brings him to another, much thornier issue that he’s been forced to navigate: “This massive, massive thing for the last five years about me being gay.”
Examples of what he means are all over YouTube and Twitter. There are memes that pair photos of Mendes with jokes about being closeted and videos that scrutinize his gestures. On some parts of the Internet, outing him has become a spectator sport. Mendes often finds himself watching his own interviews, analyzing his voice and his body language. He’ll see an anonymous stranger comment on the way he crossed his legs once and try not to do it again. He pulls out his phone to show me his Twitter account — his name is the only recent search. “In the back of my heart, I feel like I need to go be seen with someone — like a girl — in public, to prove to people that I’m not gay,” he says. “Even though in my heart I know that it’s not a bad thing. There’s still a piece of me that thinks that. And I hate that side of me.”
Last Christmas, he was reading YouTube comments about his sexuality when he decided he’d had enough. “I thought, ‘You fucking guys are so lucky I’m not actually gay and terrified of coming out,’ ” he recalls now. “That’s something that kills people. That’s how sensitive it is. Do you like the songs? Do you like me? Who cares if I’m gay?”
So he recorded a frantic Snapchat story. “I noticed a lot of people were saying I gave them a ‘gay vibe,’ ” he told his millions of followers, sounding a little choked up as he stared wide-eyed at the camera. “First of all, I’m not gay. Second of all, it shouldn’t make a difference if I was or wasn’t.”
But the video only made people talk more. Mendes mentions a text he got just the other day from Swift. They’ve been friends since she took him on her 1989 tour, when he was 16. He remembers those shows fondly — how she showed him the ropes of performing at arenas and stadiums, how she’d line up her trucks in the shape of a diamond and throw huge barbecues inside with soccer games and flip-cup. (“I wasn’t drinking,” he says. “I was just playing with water, obviously.”)
Swift was texting Mendes a cellphone video of them together, just to make sure he was cool with her posting it — a short clip of the night they were hanging out backstage at her Reputation tour and she put her glittery eye makeup on Mendes’ face, to his delight. He told her it was fine without thinking, but later that night, he woke up in a cold sweat. “I felt sick,” he said. “I was like, ‘Fuck, why did I let her post that?’ I just fed the fire that I’m terrified of.”
In the end, Mendes says, he’s happy about the side of himself shown in Swift’s backstage post. As a kid, he’d put glitter on his eyelids to make his parents laugh; he grew up with 15 female cousins, “braiding hair and painting nails. Maybe I am a little more feminine — but that’s the way it is. That’s why I am me.”
He’s beginning to see the value in letting his guard down in his music, too. “In My Blood” — the biggest hit from his new album, with more than 300 million Spotify streams — stands out with its crashing arena-rock guitars and Kings of Leon-style chorus, but also for its desperate lyrics:
Laying on the bathroom floor, feeling nothing.
I’m overwhelmed and insecure, give me something
I could take to ease my mind slowly.
Just have a drink and you’ll feel better.
Just take her home and you’ll feel better.
Keep telling me that it gets better.
Does it ever?
When the song came out in March, Mendes was in a movie theater watching Love, Simon — a comedy-drama about a closeted teenager whose sexuality is exposed by his classmates. He had a panic attack in the theater and had to leave early. Then he opened up Twitter and saw messages from people who related to “In My Blood,” from friends to a woman who played it for her daughter in a hospital. He stayed up until 3 a.m. reading the comments. “I broke down in my hotel room,” he says. “I started crying, and I was just like, ‘This is why you talk about shit that actually is real.’ I was like, ‘God, don’t ever fucking question the feeling of writing the truth again.’ ”
Somewhere above Central Europe, there’s a minor disturbance aboard an Embraer 650E jet. A series of loud shouts and stomps can be heard coming out of the plane’s bathroom. A flight attendant knocks on the door to see what’s happening, but there’s no need to be alarmed: It’s just Mendes, on the toilet with his acoustic guitar, trying to write a hit.
Taking her knock as a cue to stop, Mendes leaves and kicks back in the 14-passenger jet’s lounge area. “It’s super-Taylor Swift-inspired,” he tells me excitedly of his latest work-in-progress. “I record a shitty version of it with my phone, and if I find myself listening to it for more than a week, then it’s something.”
The jet is a new thing for Mendes. He usually flies commercial, but his label has dropped a couple hundred grand so he can hit several countries — Denmark, Portugal, Hungary, the U.K., Canada, the U.S. and Japan — for a series of festival gigs and TV shows. In the meantime, his team is living it up: Stirling, his marketing manager, has been checking out the seafood platter, while Mendes and others debate whether Michael Jordan or LeBron James would win a one-on-one match. (Mendes picks LeBron.)
Just a few years ago, in 2014, Mendes took his first professional trip, to a touring event called MAGCON, short for Meet and Greet Convention. The road show was mainly a platform for teen boys with large social followings to meet the fans who felt as though they already knew them. Mendes recalls the invitation he got from one of those stars, Cameron Dallas, a photogenic kid famous for playing pranks on his family: “He was like, ‘Hey, bro, we’ll give you 200 bucks and you’re gonna meet 500 girls.’ ”
Mendes was just starting to get traction on Vine. He’d tried posting music to YouTube with little success, but now he was reeling in tens of thousands of likes per day on covers of songs such as Bieber’s “As Long As You Love Me,” Adele’s “Hello” and Sheeran’s “Don’t.” His Vines lasted only six seconds, but some took as long as six hours to make. “I’d be sweating, but it’d be so worth it,” he says. “Every time I would make it, make it, make it until I got the feeling, whether it was the way I smiled into the camera or the tone of my voice.”
At his first MAGCON event, in Dallas, Mendes and his dad met guys like Nash Grier, who was known for Vines where he vandalized supermarkets and covered his face in flour. Most of the social celebrities in this scene entertained their fans by jumping on trampolines or breaking out bad dance moves; the fact that Mendes was passably skilled at guitar was a major bonus. “We were like zoo animals,” he says. “[Fans] would just stare at us and take photos with us. We would do whatever they say.”
Mendes estimates there were 500 fans at that first show. The next city had 800 fans, and the one after that had about 1,300. Andrew Gertler, a young marketing executive at Warner Music Group, started petitioning Mendes’ family to let him manage Shawn after seeing one of those dates; within months, he’d gotten Mendes a meeting with David Massey, a then-Universal exec who’d discovered the Jonas Brothers a decade earlier. By the summer after 10th grade, Mendes was on tour with Swift. “I went to three or four parties, then I was out [of school],” he says. “The next party I went to was Taylor Swift’s for her 22nd birthday, and fucking Beyoncé and Jay-Z were there.”
Vine would announce it was going out of business in 2016, but by then Mendes had moved on. “When I started talking to Shawn, one of the first things I said was, ‘You have to go build something for yourself,’ ” Gertler says. “I look at the relationship Jon Landau had with Bruce Springsteen. Can we tour for 40-plus years?” Early on, they agreed that Mendes would always be seen with a guitar, and he’d make a point of talking about how he writes his own songs.
The friendly, open personality that made him a hit on the MAGCON circuit has helped, too. “He had the opportunity to be a dick, ’cause he was so young and so famous,” says Sheeran, who is now a friend and mentor figure to Mendes. “But he’s genuinely one of the nicest guys in the industry.”
The jet touches down in Budapest, and Mendes’ guard’s phone pings almost instantly. “There’s fans,” he says. Mendes puts his stuff through security and quickly checks himself out in the mirror, running a hand to the back of his hair. “You’ve got the look,” he sings, putting on a Prince-ish falsetto. A wave of shrieks erupts from the parking lot. Hundreds of girls have their phones ready, chanting his name and yelling, “I love you!”
Mendes takes a picture with each one, a smile pasted on his face. After he works his way through, he blows one last kiss and gets in the next van. “Is everybody here gorgeous?” he says. “Did I stumble upon the most beautiful country in the world or something? They all have these beautiful eyes.” He puts his earbuds in and closes his eyes as we drive past Gothic stone buildings. “It’s pretty dope here,” he says, then goes quiet for a while. “I don’t know, man,” he mumbles as we approach the hotel. “I feel fucking weird.”
The next day, Mendes is sitting on the arm of a yellow couch in a trailer at Budapest’s Sziget Festival, arguing about his cooking skills. Events like this one — a weeklong party on an island in the Danube River that feels something like an Eastern European Burning Man — are a big priority for him as he works on developing a wider audience, and that includes endless quickie interviews with local press outlets that want to know about his favorite actor (Jake Gyllenhaal), his hobbies (“I’m really into fitness”) and his solution to world poverty.
Mendes is not in the mood for it right now. His voice wasn’t working when he woke up this morning, he spent last night feeling depressed in his hotel room, and the Hungarian reporter across from him keeps asking clueless questions. “I’m a horrible cook, actually,” he says. “That’s very false information.”
So what kind of things does he cook? “Scrambled eggs?” Mendes offers. “I can’t [cook]. I just said that.”
The reporter moves on. What do you think about being called the new Justin Bieber?
“I love Justin,” Mendes replies flatly.
By the time his set begins a couple of hours later, he’s turned on the charm. “Sing it!” he shouts as he takes the stage in a Springsteen-ish outfit of a white tank top and tight jeans. Later, during “Youth” — a heartfelt anthem that he wrote after the Manchester concert bombing last year — he bows his head and strums a single chord on his acoustic guitar. He stays on that chord for a long moment, hitting it more and more intensely. It looks like he’s getting something off his chest.
Afterward, Mendes is hanging out in the crowded backstage lounge under a tree decked in Christmas lights. He tells me he’s been feeling down, that the heat and travel have been getting to him. “You know when you’re in a state of unhappiness when you have no reason to be unhappy?” he says. “I hate that.” He has a trick for when he gets in these moods: “Honestly, it sounds silly, but it’s been proven to get people out of depression. I’ll stand in front of the mirror with this outfit on, shake my head, stick my tongue out and put myself in a stadium of people that love me.”
His voice is drowned out by the sound of a group of people singing “Happy Birthday” to someone backstage. For whatever reason, the song lifts Mendes’ spirits. He looks at my recorder. “Can you send that to me?” he says. “Whatever that little space of audio was, because I think it was really beautiful. I want to put that inside of a song. Don’t worry, I’ll give you a producing credit!”
Someone from Mendes’ team comes by with a tray of Hungarian liquor shots for us. “Are they strong?” Mendes says, after picking one up. “That’s classic me — ‘Is it strong?’ ” He tosses it back. “Whoa,” he says, grimacing, before chasing it with a beer. “That’s strong.”
His band heads back to the hotel, but Mendes decides to stick around. Kygo, the 27-year-old Norwegian tropical-house DJ, is in the trailer next door. They hit it off, and soon they’re venturing out of the backstage compound and into a giant VIP tent, where they get behind the bar and start serving drinks. Mendes gets into the job: “Vodka-Red Bull? I got you, brother!” he tells his first customer.
Mendes isn’t a perfect bartender — he needs to be told to put ice in a vodka-soda, and he pours a draft beer that’s 90 percent foam, ordering a guy to “drink it quick” before it dissolves. At one point, Mendes stops to arm-wrestle Kygo, who wins. But he makes another new friend: a cute Hungarian bartender who steps in to show him the ropes.
They exchange looks and get closer over the next hour, and soon they are running across the festival grounds to watch Australian dance-music act Chet Faker’s 1 a.m. set. They climb two flights to the soundboard, which overlooks the gigantic lit-up stage, and sway to the music.
Around three, it’s time to go — Mendes and his team have a 9 a.m. flight. I assume I’ll be riding home with him, but his security guard unexpectedly ushers me into another van, which speeds off without Mendes. When I arrive at the hotel, he and the bartender are getting out of a different van and heading to his room.
A few weeks later, I see Mendes at Rolling Stone’s cover shoot. He says the next morning in Budapest was rough — the Hungarian liquor has become a running joke among his crew. “I hadn’t done that in a while,” he says with a smile. Some fans have even begun speculating about the bartender, because he followed her on Instagram that night.
Actually, he adds, he didn’t: When Mendes was in the bathroom, she grabbed his phone and followed herself from his account. He shakes his head. “Gotta give her credit for that.”