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The obvious caveat to note here, at the beginning of a listicle about the best Drake songs, is that the man has released a lot of music throughout his career.

Since ‘Best I Ever Had’ made him a household name in 2009, he hasn’t really slowed down at any point, continuously putting out albums and singles, while frequently featuring on other people’s work, too. According to the Genius website, Drake’s discography “includes 1,843 songs,” so deciding on five of the best is, basically, a fool’s errand—yet, because these things can be fun to think about, here we are.

Drake’s music is undeniably popular—pretty much every major release is liable to break some pop culture records. According to Billboard, Drake became only the fourth ever artist to see 100 songs enter the Hot 100 list. An impressive feat, but he was only getting started. By 2019 he’d achieved 200, and by 2023 he’d achieved 300. No other artist has ever released so many hit singles that have entered the Hot 100, and he’s continuously adding more. Today the number of Hot 100 songs to his name is 359.

Obviously, Drake’s immense popularity has made him the focus of a lot of criticism, too—most notably, in recent years, coming from Kendrick Lamar. Certain audiences, critics and fellow musicians find his schtick intolerable—his arrogance grates, his celebrity romances generate so much tabloid fodder, and some of his actual music is unquestionably poor, which, considering he’s released more than 1,800 songs, is perhaps to be expected. The point is, people like to hate Drake.

But while there are many misses in his discography, there are more than a few hits. One can’t reach the level of success that Drake has without having a solid sense of how to put together a good song, so here’s an attempt to pick out five of the best.

Five best Drake songs of all time

‘Take Care’ ft Rihanna

The core of ‘Take Care,’ musically speaking, is fairly complicated—it’s a sample of a remix of a cover of a song recorded for the first time back in 1959. That original song, ‘I’ll Take Care of You,’ was written by Brook Benton and was recorded by Bobby Bland, but, over the course of several decades, it would live a life that would ultimately see it inspire a track by Drake and Rihanna. Many artists have covered the song, but one of them was Gil Scott-Heron, whose version was remixed by Jamie xx. It’s this remix that was reworked for the Drake track.

‘Take Care’ is the title track of his second studio album, which came out in 2011, and that phrase, “take care,” is something he came up with while he was in Birmingham, of all places. “I came up with the name when I was on a bus in Birmingham, England, going to a show,” he explained to GQ around the time of its release. “‘Take Care’ is this thing we use in passing conversation to dismiss bullshit like, ‘Oh, you couldn’t make it on time? Oh, take care, take care.’ We’ve always used that and then I really took so much care making this album. I knew I was going to go home and take longer than six months, I knew that I was literally going to take care of making this project and be attentive, be clear, be immersed in it. ‘Take Care’ worked.”

‘Know Yourself’

With the release of ‘Know Yourself,’ lifted from his 2015 mixtape If You’re Reading This It’s Too Late, Drake gave his home city of Toronto something which, arguably, it had never had before: a true, pop music anthem known all across the world. ‘Know Yourself’ grew to become just that, and, impressively, it seems that that was Drake’s intention the whole time. He’d purposely created a song that would put Toronto on the pop culture map, after being inspired to do so by one of his American contemporaries.

“I always used to be so envious, man, that Wiz Khalifa had that song ‘Black and Yellow,’ and it was just a song about Pittsburgh,” he told Fader in 2015. “Like, the world was singing a song about Pittsburgh! And I was just so baffled, as a songwriter, at how you stumbled upon a hit record about Pittsburgh. Like, your city must be elated! They must be so proud. And I told myself, over the duration of my career, I would definitely have a song that strictly belonged to Toronto but that the world embraced. So, ‘Know Yourself’ was a big thing off my checklist.”

‘The Ride’

Drake does something risky right at the start of ‘The Ride’: he kind of disses his own fans. “I hate when, I hate when people say they feel me, man / I hate that shit / It’ll be a long time before y’all feel me / If ever / For real.” The track that then follows suggests that, for all his braggadocio, Drake actually struggles with fame sometimes. The song is arguably undercut with a sort of gentle melancholia, a sense of a man subject to an alienation that only megafame and success can bring.

When Drake eventually begins to rap about the usual tropes of having sex with beautiful women and making lots of money, it doesn’t come across as cocky as it normally does. He just seems kind of numb to it. Almost like fame has robbed him of basic human joy and experience. It’s the sort of admission one wouldn’t expect to come from a star like Drake.

‘Forever’ ft Kanye West, Lil Wayne and Eminem

‘Forever’ was a statement of intent by Drake. He hadn’t yet become the star we know him as today, but, by pulling together huge rap stars like Lil Wayne, Kanye West and Eminem for the track, he demonstrated to the world that he was the real deal. He certainly wasn’t short of confidence at this early stage in his career: “Killin’ all these rappers, you would swear I had a hit list,” he raps. “Everyone who doubted me is askin’ for forgiveness.” Audiences went for the cockiness, which, maybe, was easier for them to do given that Wayne, Kanye and Eminem all seemed to trust him. Why else would they have agreed to rap on ‘Forever’?

Eminem’s verse certainly elevated the track, injecting it with a frantic sense of urgency. Complex asked him about it in 2009, and, in response, Slim was humble. “I like everybody’s verses,” he said, “but I like Drake’s verse a lot. I wouldn’t say I had the best verse; everybody approached the beat different. Kanye was crazy, too, and Wayne. I just saw the beat differently than anybody else did; for some reason, I felt like the beat was a double-time beat, so I rapped faster.”

‘Pound Cake / Paris Morton Music 2’ ft Jay-Z

Drake’s third studio album, Nothing Was the Same, closes with two songs knitted together: ‘Pound Cake’ and ‘Paris Morton Music 2.’ As in ‘Forever,’ Drake again shoulders his way to the top of the rap game by trading verses with Jay-Z during the ‘Pound Cake’ portion of the track, ultimately holding his own against Brooklyn’s finest. The producer behind that ‘Pound Cake’ bit was Boi-1da, who, in 2018, spoke to Noisey about it, offering readers some insight into how it was put together.

“I was trying to go against the grain and get my own kind of bounce,” he said. “I was thinking of something very simplistic for Drake to get some bars off, and I thought that was very much fitting.” That simplistic approach also saw Boi-1da keep the tempo really low, reminiscent of an earlier day in hip-hop history. “The whole song turned out really special,” according to the song’s producer. “It’s just such a chill song. The beat really matches hookah vibes.”