It's a few minutes past 7 and James Blake and his bandmates are sitting in a trailer, still buzzing from their performance to a half-full amphitheater. Blake's manager, Dan Foat, takes a sip of a beer and admits, "Everybody's looking at us like, 'Who are these skinny British guys?'" By everybody, Foat means the intimidating security, anxious fans and even some of the fellow artists at Drake's OVO Fest in Toronto, and though Blake is an invited co-headlining guest here, he and his crew are clearly out of place.

Really, the electronic singer/songwriter is only here by circumstance. He was initially scheduled to perform during the first day of the festival, alongside an equally-alternative Frank Ocean, but after Ocean sustained a vocal injury, Blake was left alone as the only non-hip-hop artist on the bill. Even with Drake cutting his hometown party down to one day from two, he still wanted Blake to perform, so much so that he squeezed Blake's set in at the last minute and scheduled him for a 7 p.m. slot, with the summer sun overpowering the venue and its occupants. It's far from the twilight hour in which Blake prefers to perform, but the U.K.-bred musician is happy to be here. "Now we get to play for Drake's fans," he said earnestly before his set, "which is a silver lining."

Blake is aware that Drake's fans are not his own, but that might not be the case for long. After all, OVO Fest is just another moment in a long-brewing relationship that has found the universe pulling the two forces together. In March of 2011, Fader published a cover story on Blake, in which the writer and the subject started out at a Drake concert. At OVO, Blake explains that the profile happened before he'd even met Drake, but afterward he was inspired to delve into the Toronto native's back catalogue. He admits that he liked the way Drake was making hip-hop.

Then on Memorial Day of this year, a "fake" tracklist of Drake's forthcoming Nothing Was The Same leaked, on which Blake was credited for producing a song called "Her Regrets." That placement came as a surprise to some, but only those who had neglected Blake's recent love affair with hip-hop. In the past year, Blake collaborated with RZA on "Take A Fall For Me" from his sophomore album Overgrown; rumors swirled about Blake working with Kendrick Lamar, which went on to be both confirmed and denied by both parties; Mississippi rapper Big K.R.I.T. released a black and white video for "R.E.M.," which sampled Blake's "The Wilhelm Scream"; and during a rare Twitter Q&A with his fans, Jay Z admitted that Blake was one of the only non-rap artists to whom he'd been listening. "Each of those people, I've listened to their album a lot, and they've got in touch and said they listened to my album," Blake explains. "And that's something that's very flattering… That's about as organic of a way as you could want to be on someone's radar. It's not business, it's just music."

At OVO Fest, no one in attendance seems to notice that the withheld, wiry 24-year-old in all black is the the artist on every rapper's mind. But as he walks from his trailer toward the stage, a blacked-out Mercedes rolls down its window and Kanye West (a surprise guest here) stops Blake in his tracks. For minutes, the two talk about whatever it is Kanye West and James Blake have to talk about, and just like that, the window is rolled up and Blake walks off. Later, rumors will circulate that Diddy is also dying to meet Blake.

By the time he makes it to the stage, bros in owl-emblazoned (Drake's unofficial logo) hats and underage girls with butt cheeks peaking out of their shorts are spilling into the arena in growing numbers, but if anyone is excited to see James Blake perform, it's hard to tell. Still, he quickly takes his place behind a rig of synths and leans into a jarring and evocative set that he starts off with spooky, booming renditions of "I Never Learnt To Share" and "The Wilhelm Scream." As he gets into "CMYK"—an expertly looped and undeniably groovy cut from one of his earlier EPs—the bros and their babes can't deny the swaying energy of Blake's more upbeat work. Blake ends his set with "Retrograde," a sweeping ballad from his recent album—and his biggest hit to date—with a sparse, looped hum and distant clap that finds him gasping for affection. Watching him belt it out to a still-filling-out stadium, it's hard to believe someone so interior has such an enormous voice.

Backstage after the performance, Blake concedes that he wishes he'd performed to an evening crowd, but he made due, and again, he's happy to be here. And then Ma$e—the legendary Bad Boy rapper-turned-pastor—walks by. Though Blake has never listened to his music, he's heard of him, and is surprised to see him here. The reality of Blake and Ma$e being in the same room is hard to make sense of, but alas, this is the magic of someone like Drake. He's able to bring these two disparate entities together.

"Drake has pretty broad tastes," Blake says later. "You find that with people who are really into music, they're very often not just listening to one kind of music. While he makes hip-hop, that doesn't stop him from liking other music." Despite occasional ridicule, the general public has come to accept Drake's divergent tastes, because he collaborates with artists in earnest and is able to meet them in their own comfort zone. In recent memory, the Canadian rapper has worked with lo-fi producer Jamie XX, left-field crooner Sampha and soul icon Stevie Wonder. These are very clearly the liner notes of an eclectic man, but just as Drake has been celebrated for his daring entrees into outside genres, Blake's acceptance into the hip-hop world has been a bit less fluid.

Still, with a resume like his, it's clear that there's some sort of connection between Blake and the genre's biggest names; something that would explain the mysterious mutual respect. "I grew up in a lot of similar music," Blake asserts, cutting through any hypothetical reasoning. "Not necessarily that I discovered hip-hop that early, but my influences are mostly Black American music. The song I was singing to warm up before I went onstage was 'Trouble Blues' by Sam Cooke. That gives you an indication of where I come from, from a musical perspective." With firm roots in American blues, what Blake and his hip-hop counterparts lack in sonic overlap they make up for in stylistic similarities, namely the ability (and bravery) to delve into subjects like solitude and sensitivity in sincere, emotional ways.

When asked about Drake's self-reflection, Blake eagerly admits, "I like that in him." Later in the evening, Drake will play his Destiny's Child-sampling "Girls Love Beyonce," a through-and-through R&B song about getting burned and feeling isolated in a relationship, which Blake describes as having "a lot of vulnerability." True as that may be, the two differ in an important and obvious way—where Blake is always "on," singing effortlessly about discomfort and loneliness, Drake is as prone to pen "Beyonce" as he is to rap about Miami strip clubs on a braggadocios radio hit (see: "All Me").

He's also minutes away from all but ditching his vulnerable side to put on his very own rap all-star show that will feature performances from just about every swag-obsessed artist in the world, from Diddy to Lil Wayne to Big Sean to French Montana. This speaks to Drake's fan base more than it does to the actual individual.

While Drake and Blake are not-so-different artists who find ways to meet in the middle with their music, their fans are as different as can be. Where Drake is most celebrated for his bravado and his cosigning of the "who cares?" YOLO lifestyle, listeners of Blake's music are often reminded of their own frailty and the harsher side of the fact that they only LO. They're both vulnerable, sure, but the way they're experienced by fans puts them at opposite ends of the vulnerability spectrum, with different live show expectations to live up to.

After loitering in his trailer after his set and geeking out about the Roland TR-808 and the Teenage Engineering OP1 Synthesizer, Blake, his manager and his girlfriend—a fellow musician he met at Barcelona's Primavera Sound Festival—make their way back toward the theatre and pass by a battalion of high-end cars and a frantic 40 (Drake's longtime producer) before ducking into the side-stage area where All Access guests are permitted to stand and watch Drake's unfolding event. Nobody notices James, and he seems to prefer it that way.

For two hours, he and his girlfriend (who's only slightly more enthusiastic) serenely stand by and watch the over-the-top ridiculousness that is OVO Fest unfold. His eyes widen at certain moments, like when Lil Wayne hops onstage, and even occasionally flashes a timid dance move to some of his favorite cuts (i.e. Big Sean performing G.O.O.D. Music posse cut "Mercy"), but on the whole Blake's a stoic onlooker. Though the festival wouldn't make sense for someone as understated as him to enjoy, later he diplomatically declares, "There was a lot of energy in that show." Does that mean he would ever try to put a show like this on himself? He clarifies, "You can create energy in loads of different ways."

Long after his manager and his bandmates have left the venue, exploring Toronto for better prospects than a Drake concert, Blake remains, and sees Drake's set through to the end. As the lights go up and 20,000 people pile out of the amphitheater, James follows his girlfriend to the backstage area and shoves through the masses of fans but gets stuck in a security standoff. Exalted concertgoers hover around, hoping for an encore from Drake, and one looks over at Blake and yells, "James Blake! You're fuckin' awesome!" Blake doesn't notice, and neither does anyone else, and just like that he disappears, just another Drake fan in the crowd.