Drake has redefined rap’s sound and the way we consume pop music. Pound for pound, he might be the most successful rapper of all time. He’s one of the only true music stars of the new millennium, and in his home country of Canada, he’s probably the most powerful person who’s not an elected official. In addition to being one of the most charting artists of all time, Drake has landed as many hit songs for other artists as he has for himself. Sure there’s the undeniable talent, work ethic, beat selection, genius collaborators, and classic videos, but the true key to Drake’s longevity is his versatility.
Folks often forget that Drake’s breakout release was a mixtape. So Far Gone feels like a truer release than his official debut, Thank Me Later. His hybrid of croon-rapping would redefine what was acceptable for rappers to sound like. It wasn’t just versatile — it was effortless, as he pivoted between styles. 808s & Heartbreak had only been out for a few months, but Drake was already pushing despondent, singing-infused rap into new territory. The pliability displayed on So Far Gone was just a jumping-off point. Drake got better at rapping and singing. Doing both in tandem gave him the ability to show up on anyone’s song and knock it out of the park.
Rapping or singing, verses or hooks, it didn’t matter. By the time he was hitting his stride, Drake was beating most of his contemporaries at both. He did it on his own songs and with his guest spots. A Drake co-sign was worth its weight in gold, even if he showed up every collaborator.
This ability to cross genres and maintain quality endeared him to a much wider audience than he if he’d stuck to just rapping. Because of that, Drake’s biggest competitor on the charts has been himself. These multiple personas – singing Drake, hedonistic Drake, or embittered Drake – lets him appeal to every kind of music fan.
Listen to the best Drake songs on Apple Music and Spotify.
The Hits
(Best I Ever Had, Started From The Bottom, Hotline Bling, God’s Plan)
Compared to some of the best Drake songs named here, “Best I Ever Had” doesn’t feature his best rapping or singing. It almost sounds quaint, because of how immediately his flow would become more boisterous and his singing more elastic. The jump from Thank Me Later to Take Care feels massive. But “Best I Ever Had” is still one of the most quintessential Drake songs: other than being hugely popular, it also marked his ability to make songs that sounded like love songs but are really true player’s anthems.
Nothing Was the Same’s “Started From the Bottom” wasn’t just Drake’s biggest single to date, it marked a turning point in his career when his ubiquity reached new levels, on and off the charts. Drakeisms working their way into everyday speech coincided with brands discovering social media, and the result years later is that a Drake song released on a Thursday night has spawned four catchphrases by Monday. It also featured Drake just straight-up rapping in a way that pleased his die-hard fans and built up a ton of excitement for NWTS.
“Hotline Bling” was another moment when Drake surpassed himself on the charts, but the first time one of his videos took on a life of its own. There was a dance. There were memes. There are still memes. He didn’t look back after this. He embraced it and started going bigger with each video. Scorpion’s lead single “God’s Plan” would follow in the footsteps of both “Hotline” trends, becoming Drake’s biggest single of all time and propelling his videos to new heights.
The Lay-up Bangers
(Worst Behavior, Draft Day, Energy, 0-100)
The songs that truly define Drake as a rapper didn’t arrive until later in his career. By the time Nothing Was the Same came out, he was the most dominant rapper on the planet. He was now in a tier of his own, which meant he got to make songs like “Worst Behavior.” He wasn’t just consciously rapping circles around everyone else, he was doing it over beats that felt experimental, and explored new sounds for Drake. This new level of brashness wasn’t going anywhere.
2014’s loosie “Draft Day,” now included on the B-sides compilation Care Package, was notable both for bagging a rare Lauryn Hill sample, and its heavy sports shoutouts. He name drops Cleveland Browns quarterback Johnny Manziel first, but the reference to Golden State Warrior Andrew Wiggins is more appropriate, given that Drake was clapping on the sidelines of every televised NBA game. A long time ago Drake rapped of artists and athletes, “we wanna be them and they wanna be us.” Hip-hop and sports have always had a symbiosis, but like everything else Drake, has elevated this relationship to new levels. What other rapper is famous for riding on team planes?
“Energy” is “Worst Behavior” on performance enhancers. As a title, Nothing Was the Same has a little bravado, but mostly sounds bittersweet. Being at the top makes you a villain, and Drake was embracing it. He has never replicated the braggadocio on the A-side of If You’re Reading This It’s Too Late, and “Energy” is still the standout of that run. The album’s release felt like a victory lap, but “Energy” was more of a warning than a celebration.
As of this writing, the gap from Nothing Was the Same to Views is the longest period between studio albums of Drake’s career. When he dropped “0-100,” Drake was gearing up to drop an album in Spring 2015. This didn’t quite happen, but we did get If You’re Reading This. And while “0-100” was only ever a promo single, it showed that Drake could get more longevity out of a single, than most artists could get with an album.
Singing Drake
(Take Care, Started From The Bottom, Hold On, We’re Going Home, Feel No Ways)
Take Care’s title track was another “moment” for Drake and bolstered his legitimacy as a singing rapper. Due to their chemistry on and off tracks, every collab he did with Rihanna would not only top the charts but provide grist for the gossip mill. “Started From the Bottom” follows in the tradition of Thank Me Later’s “Over” and Take Care’s “Headlines.” It was the first single off the album and featured Drake rapping more than singing. For the fans who thought Take Care had maybe too much singing, this was a salve. It also marked a new direction (with some help from Mike Zombie) and was one of the “hardest” songs thus far to appear on a Drake album.
One of Drake’s finest singing moments comes from an album with the least amount of singing on it, outside of the hooks. “Hold On, We’re Going Home,” is the only time things slow down on Nothing Was the Same, but it’s proof that people like what they like, and Drake knows it, because it was just as colossally popular as “Started from the Bottom.” In some instances, his singing would overshadow his flow, as with the case with Views. It feels like Drake’s “rainy day” album, consisting of grey and blues, and even “Hotline Bling” seems a little somber. For one of the most popular songs of the last decade, Drake still manages to make it sound intimate.
“Feel No Ways” is another one of Views’ standout moments. On a track that barely contains anything that could be considered rapping, you get classic introspective Drake, singing about a relationship and turning his commentary into a mantra for himself. “Controlla” and “One Dance” would be the massive singles, but “Feel No Ways” feels much more personal.
Collabs
(No Lie, Mercy, Versace, Diamonds Dancing, I’m On One)
A year after Take Care, Drake was gaining steam. As a featured artist, he went from collaborator to kingmaker. Some of those features turned into relationships that lasted over a decade, as was the case with “No Lie.” Drake’s stamp of approval helped 2 Chainz follow up a massive verse on “Mercy” with a single of his own that was just as big. They’ve been working together ever since, with Drake calling 2 Chainz one of his favorite rappers.
The next summer, Drake had a similar effect on Migos’ “Versace.” This time, he dropped a verse on a single that was already out. Migos’ popularity skyrocketed overnight, and Drake got to show he had his finger on the pulse. He wasn’t just part of the zeitgeist anymore, he was shaping it. But the most fruitful collaboration in Drake’s career is his relationship with Future. This synchronicity would reach its peak on their collab mixtape, What a Time to Be Alive, and its standout single “Diamonds Dancing.”
“I’m On One” is quintessential Drake, but it’s also the quintessential DJ Khaled song. Khaled’s chemistry with Drake, Rick Ross, and Lil Wayne has always been great, but “I’m On One” is the best of all these worlds, with each rapper delivering a classic verse and Drake dropping an all-time hook. It’s a party song, it’s a somber song, it’s a drug song, it’s self-reflective and paranoid… it’s pure Drake.
The Storyteller
(Look What You’ve Done, Too Much, Weston Road Flows)
Drake’s fame and chart success sometimes hide just how honest he gets. He’s easily one of the most lyrically-driven, popular rappers ever, especially when it comes to talking about his family. “Look What You’ve Done is a great title because of how accusatory it sounds when it’s really a somber celebration of the people in Drake’s life. He speaks on his parents and their divorce, his uncle, peoples’ homes where he spent time with exes, and his struggles with childhood fame. He caps it off with an outro from his grandmother, and the tenor of his voice over the whole thing is unforgettable.
“Too Much” occupies a similar position on Nothing Was the Same’s as “Look What You’ve Done” does on Take Care, and the song feels very much like a sequel. Just a few years later and Drake sounds brasher and more jaded. He ends the first verse considering the crowds at his old hometown shows compared to the ones he could pull now, and the second verse contends more aggressively with his relationship with his father. By now, Drake’s parents are celebrities in their own right. They’ve made tons of appearances with their son and are part of his mythology. Until Views, we never got a real look – through Drake’s own lens – at his adolescence.
Everyone knew about Degrassi, but most of the time it was a chapter he’d rather not revisit. Songs like “Weston Road Flows” changed that for good. Drake’s eating junk food and smoking weed in basements while his friends’ older brothers play chaperone. Situations like this permeate the album, but “Weston Road Flows” goes even further and eventually finds Drake reflecting on how far away he is from his old neighborhood – his friends, family, ex-flames, and hangout spots — both physically and spiritually.
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