On a frigid night last month, three groups of friends took turns knocking through twangy covers of the usual suspects: The-Dream, Bone Thugs-n-Harmony, the Cardigans. There was no stage, just a d.j. booth and a microphone, and song choice grew paramount. The courteous tried to entertain the mostly empty room, and muted competition grew between our cluster of regulars seated at the bar, a pair of young women in leather pants sitting in an alcove, and a few nondescript strangers at far tables. As nerves eased, the numbers got wilier. Props were utilized; a latecomer knee-slid into a performance, mid-song. Just as the session had reached perfect pitch, however, it was thrown into a tailspin. After the first few taps of an icy note and a familiar vocal riff, the group heard where our new challenger was heading, and stared in disbelief. Seriously, who performs Frank Ocean’s “Pyramids” at karaoke?

“Pyramids,” the lead single to Ocean’s “Channel Orange” album, from 2012, is over nine minutes long. The track’s initial arrival was not unlike its appearance at our karaoke session: unexpected, perplexing, and knowingly disruptive. An impressionistic prog-funk epic about an Egyptian queen and a stripper in a motel was not the sticky sing-along Ocean felt so capable of when early fans and critics flocked to his self-released mixtape. Similarly, his second album campaign began with “Nikes,” a crawling, chipmunked free verse over minimal trip-hop, which sounded just as intentionally out of step. Traditionally, big artists release big songs in hopes of a big album; radio plays and plays, stoking anticipation, and release dates are climactic as fans collectively dig down the single’s rabbit hole. By contrast, Ocean’s first offerings seemed designed for the fan to appreciate alone in silent awe, but not exactly to belt with friends in dingy bars.

Ocean has as complex a relationship with this system as he does with the other music-industry pillars that he pined over as a child: the charts, the labels, the Grammys. In 2012, he described the radio as “a conveyor belt with little soul” to me. “When I think of ‘single,’ I automatically picture putting something that I’ve put everything into on some conveyor belt,” he continued. Last year, in his first major interview supporting “Blonde,” he told the Times, “It’s not essential for me to have big radio records,” before admitting that he obsessively studies his streaming tallies. On the first episode of his own radio show, “Blonded,” a Beats 1 program that beams into the palm of anyone with an iPhone, he featured an excerpt of a conversation he had with Jay Z, who shared his disappointment in the medium’s state. “You take these pop stations, they’re reaching eighteen-to-thirty-four young white females. So they’re playing music based on those tastes,” Jay observes. “And then they’re taking those numbers and they’re going to advertising agencies, and people are paying numbers based on the audience that they have. So these places are not even based on music. Their playlist isn’t based on music. If you think, a person like Bob Marley, right now, probably wouldn’t play on a pop station. Which is crazy.”

A few nights after karaoke, Ocean released “Slide,” with Calvin Harris and Migos. The collaboration was unexpected from Ocean, a typical soloist, featuring two linchpins of pop radio’s split loyalty to euphoric dance music and bass-heavy Southern rap. (Flip on your local pop dial now, and you’ll likely hear “This Is What You Came For,” “Bad and Boujee,” or something that sounds like one of them.) Days later, on the second episode of “Blonded,” Ocean and his co-hosts played songs by Mary Lou Williams and Usher, before launching into the night’s surprise main event: “Chanel,” a shiny new original, which looped on the station for an hour straight. After decades of dodging pop standards and practices as a statement of integrity, Ocean seemed to have changed his tone in two weeks.

Listening to “Slide,” my first thought was of the poor soul at karaoke who struck too soon. Here was the Ocean song he’d been waiting for: an effortless mid-range chorus over Bruno Mars-ian grooves, two-stepping near the Weeknd’s winking retro-futurism, with handclaps to boot. While recording, Calvin Harris played each of the song’s instruments live: his arrangement is too languid for the kinetic Chris Brown and too analog for Drake’s 808-laced heartbreak, while being perfectly tuned to Ocean’s ambling delivery and happy/sad puns. “All this jewelry, ain’t no use when it’s this dark,” Ocean sings, on a track as revelatory as a light switch. His follow-up is just as focussed, despite a looser structure: two lines of minimal piano and light-touch drums, and the dazzling punch line, “I see both sides like Chanel.” A fractured identity expressed through a luxury logo—is there a better lyric anywhere on air right now?

These latest singles are both high marks in Ocean’s catalogue—among his best songs ever—and their stylistic achievements can’t be detached from their commercial ambitions or his newfound independence. Frank Ocean is making pop, and if the distribution channels allow, pop may be better for it. “Slide” debuted at No. 34 on Billboard’s Hot 100, giving Ocean the first Top Forty début of his career; the following week, it dropped to No. 52, and has hovered around the center since. “Chanel” had its world première on Ocean’s own show, an increasingly common practice that has essentially revived radio premières; this week, it ranked at No. 72. These are, by any measure, radio singles, by a world-famous, Grammy-nominated artist with a No. 1 album, and they represent a breakthrough for his short career. We now know what Frank Ocean sounds like on the radio; what’s more exciting is the idea of what the radio might sound like with Frank Ocean.

As artists and labels alike get their bearings in music’s streaming era, radio’s role is shape-shifting. It is far from irrelevant, still offering musicians the biggest reach possible for their material, but modern commercial radio is also a sound, a feeling, and a sub-scene of its own; the Chainsmokers, or, say, Desiigner, could even be called radio artists. Figures like Ocean, who have found creative comfort by keeping to the underground, might make their best work by gunning for a shrinking slot on terrestrial airwaves. A “radio record” hardly means what it did a decade ago, anyway. The descriptor is now more intuitive, like choosing the right song at karaoke: there’s not quite a science to it, but there are a few tried-and-true gimmes, and you know a good one when you hear it.