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Back in 2019, Drake dropped a compilation of loosies he released throughout the years called Care Package. It was a welcome addition to his discography because some of the songs were never mixed properly or high quality enough to really enjoy. But there was one song missing: a little ditty he made in 2016 with a then-ascendant Tinashe. The song feels like a first version or a well-done sketch as it ends abruptly and, elsewhere, Tinashe seems to still be feeling out how she would like certain parts to sound. Drake, of course, is the consummate hitmaker, setting the tone with the first verse as the song begins to build to a catchy chorus that deserved better than to be left in YouTube purgatory. — Damien Scott

This 40-produced track wasn’t an immediate standout on Drake’s watershed sophomore effort. Tender and ethereal in the way the best Drake R&B songs are, “Doing It Wrong” finds Drake at the end of a relationship, talking with a now-ex about why they’re better off apart and why he can’t stay to support her in her time of need. The warmth of the production eases the coldness of the song’s message, but if that’s not enough, stay for the Stevie Wonder harmonica solo at the end. That’s sure to cheer you up. — DS

I remember being upset at the title of this song when it first dropped. Why name an R&B joint “Wu-Tang Forever”? My stance softened once the Wu cosigned the song and were even rumored to appear on the remix, which unfortunately never happened because they turned in hardbody verses, instead of ones more line with the original song, according to U-God. But, honestly, this was a genius flip of “It’s Yourz” by 40 and it has aged incredibly well. He weaves in and out of buttersoft R&B crooning for the ladies and hardbody bars for the rap heads with elite precision, like DeNiro handling the whip in Ronin. — Angel Diaz

You’d be forgiven for having mixed this up with any number of B-side cuts from Love/Hate or Love vs. Money; The-Dream isn’t just the spiritual north star behind the fluorescent synths and splashing drums on “Shut It Down,” he’s also a writer and featured singer on the track. But certainly no arguing with Mr. Nash at his turn-of-the-‘10s peak, and Drake still makes the track his own with signature corny-but-fair-enough lyrics like “I feel like when she moves/ The time doesn’t.”  — Andrew Unterberger

First dropped in 2014, this PartyNextDoor-produced cut got a proper release in 2019 on Drake’s loosie collection, Care Package. Over dizzying chords and pulsating synths, Drake oscillates between bombastic claims, ostensibly trying to hype himself before calling or texting a certain love interest (“Waiting on you to give in and hit me up, so I could fall through like old times and hit it up!”), and more demure pleading (“I’m terrible at inviting myself, call me over…You can be the one to take control, call me over.”).  Who’s he talking about? Who knows. But right before he talks about going to Erykah Badu’s crib to drink tea and talk about love, Party slyly slips in a muted sample of Rihanna’s “Stay.” — DS

Drake and 40’s penchant for taking hits from the late 90s and submerging them until they contort and dissolve was first seen on tracks like “Bria’s Interlude.” Built around Missy’s “Friendly Skies” track from her 1997 debut album, the So Far Gone cut feels like an ode to the intergalactic soul that came out of Virginia 30 years ago. Between robotic quips and other clutter, Omarion and Drake croon their hearts out. The vocal effects makes it seem as if the two are pleading their case to their respective interests by leaving messages on an old school answering machine. But, like nearly everything else on that mixtape, it works. — DS

Before his surprise mixtape If You’re Reading This It’s Too Late, Drake’s third album was his most rap-focused studio release, boasting hits like “Started from the Bottom” and “Worst Behavior.” That said, it also featured some of the strongest R&B of his career. A great example being the woozy Hudson Mohawke-assisted “Connect.” Syrup drenched chords and screwed vocals lets Drake do his wistful recalling of failed relationships thing, while doing his best not to come off as the wealthy, successful but forlorn artist. “Oh, the idea is fun.”  — DS

Despite the name, “Karaoke” isn’t terribly likely to get the whole room singing along: It’s a little too distant, too minimal, too falsetto-driven, too hookless, relatively speaking. But it’s also one of Drake’s most sublime early works, with a gently knocking drum shuffle that could’ve been cribbed from a Massive Attack LP, and near-new-age keys that both chill and bum you out a little more with each throb. And when the title does show up, it’s in an all-time Drake-only bar: “I remember when you thought I was joking/ Now I’m off singing karaoke/ Further than I’ve ever been.” — AU

“Why do I want an independent woman to feel like she needs me?” Drake asks over a smothered sample of Ray J’s “One Wish.” “Redemption” is the type of R&B track Drake excels at making: Slow, brooding, and ever-so-slightly disrespectful to the woman he’s working so hard to court. “I’ve lost my way,” he sings as he pleads his case to a lover who has clearly decided that all his issues and insecurities proved to be too much. And despite him saying “I know” and owning up to it all, he still blames her. Before “toxic R&B” became a thing, there was Drake’s caustic balladry on songs like this. — DS

Drake nearly broke the internet when he all but confirmed the rumors that he was dating Jennifer Lopez by posting a snuggly couch photo of the A-list duo in December 2016. Months later, Drizzy leaned in and sampled The Bronx icon’s “If You Had My Love” for the swooning “Teenage Fever.” The 6 God giddily muses about his latest fling who he hopes to continue seeing. Reeling in one of his alleged childhood crushes has Drake on Cloud 9 and the euphoria seemingly gave him a new lease on love. Drake flipping J. Lo’s hit into his own romantic anthem may have come off a bit selfish, but it was brilliant. Lopez even returned the favor covering “Teenage Fever” at a 2018 concert. — Michael Saponara

One of Drake’s most fan-beloved deep cuts, “Feel No Ways” jumped off the Views tracklist like a second “Hotline Bling” in waiting. Transfixing from the first pops and locks of its Malcolm McLaren-sampling groove and Drake’s one-beat-early entrance, “Feel No Ways” is pure pop&B perfection, finding that ultimate 6 God sweet spot between sentimentality and self-righteousness. Still unthinkable it was never a single, but the lack of wear through memes and overplay means it still hits as good as the first time eight years later. — AU

In 2015, the King of IG quotables revealed a profound truth in the opening line of “Jungle”: “These days I’m letting God handle all things above me.” Nestled within his 17-track masterwork, If You’re Reading This It’s Too Late, “Jungle” is not mere filler but a poignant reflection of Drake’s tug-of-war between fame and his uncharted path in love. Amid his success, a vulnerable Drake acknowledges his need for personal growth, singing: “Still findin’ myself, let alone a soulmate.” — CL

Drake’s affinity for strip clubs began when he crafted 2009’s So Far Gone standout “Houstatlanavegas.” After two years, his love grew fonder, as proven on “The Real Her,” where he falls head over heels for a bodacious dancer. Smitten by her pole tricks, Drizzy is ready to take a knee and propose. Conversely, Lil Wayne and Andre 3000 appear more apprehensive, especially the latter, whose real fear is catching “rabies” during his steamy encounters. Though these three offer different perspectives on strip club etiquette, it’s clear why these after-hours spots sit high on every rapper’s to-do list. — Carl Lamarre

So Far Gone wasn’t Drake’s debut mixtape, but it was the one that laid the foundation for the artist that would go on to dominate the rap game and the whole of pop music. A big part of that foundation was the story of how a young kid from Toronto would make frequent trips to cities in the South to visit family and friends. And, while there, he would do his best to support the local economy by spending an inordinate amount of money in strip clubs. Produced by 40, “Houstalantavegas” tracks the life of a dancer he would be with if only she agreed to change her lifestyle. The teetering between shame and sincerity coupled with the submerged soulful trap soundtrack would become a Drake hallmark. — DS

Drake was really in his bag here. The beat by Cadastre, the hook sampling Nicki and DJ Boof at Powerhouse, the sound of disappointment in Drake’s voice at his girl and her shenanigans all combine like Voltron to form one of his best songs. The richness, depth, and the roar of the crowd after Nicki’s acapella provide an atmosphere perfect for those solo, mind-clearing late night rides as you contemplate meaningful relationships that have gone sour. His girl was pillow talking, manipulating friends, and thirsty to stunt on the ‘gram because she’s actually empty inside? Like, damn, ma, that’s how you feel? — AD

“I’m the man. Yeah, I said it. Bitch, I’m the man. Don’t you forget it. The way you walk? That’s me. The way you talk? That’s me. The way you got your hair up? Did you forget? That’s me. And the voice in your speaker right now? That’s me.” If you never heard this song and just read those lyrics for the first time, you would likely assume Drake rapped them with the same cutting timbre used on songs like “Worst Behavior.” But, no, he glides through those bars with the same breathy falsetto that helped propel a bunch of his early hits. It’s a jarring juxtaposition but it works beautifully. It also makes the actual rap verse that follows feel more tender and honest. — DS

First, round of applause for 40. His brand of subaquatic boom bap was the driving force behind not only a bunch of songs on this list, but a lot of Drake’s biggest hits. Here, he ingeniously flips all three of the “I Dedicate” tracks on Brandy’s debut album, using them all in distinct ways. One is stretched like taffy to allow for the loping bassline and the skittering drums while the others are chopped and sped up to accentuate Drake’s sing-songy flow as he details all the reasons a woman should stick with him despite her having a man and him having several other prospects. Regular Drake stuff.  — DS

Dubbing 2017’s More Life a “playlist” allowed Drake to mindlessly create without the high-pressure stakes of an official LP being burned into his discography. The freedom saw Drake continuing to explore dancehall vibes and he stumbled upon a crown jewel with “Passionfruit.” Drizzy drowns himself in the mental warfare that’s come with the strains of a dissipating long-distance relationship as OVO fans wondered if the flights were to Rihanna, Jennifer Lopez, or then-emerging UK singer Jorja Smith. A line can be drawn from “Passionfruit” to Drake’s experimental house project Honestly, Nevermind, which arrived five years later in 2022. — MS

On “Jaded,” the 6 Side lieutenant relives the horrors of a past relationship, circling back to his faults and miscues over a younger woman. Though the internet alleged the girl in question is R&B singer and one-time collaborator Jorja Smith, Drizzy remains mum on the lady’s identity. Instead, he nimbly throws darts at his ex-flame, seeking retribution for her unforgivable gaffes. “You had potential, I coulda shaped it,” he sings. With Ty Dolla $ign filling in on the ad-libs, “Jaded” is an instant classic and chilly reminder of why Drake always gets the last laugh. — CL

Drake wasn’t the first artist to rap and sing in equal measure. Lauryn Hill brought home five Grammy Awards off the strength of her ability to do both at an insanely high level. But in a post-Drake world, the onus is no longer on the rapper to tap an R&B singer to belt out a heartfelt chorus to match some verses about love and loss. As a matter of fact, a traditional rapper and R&B singer collaboration is rarer than a coherent Meek Mill tweet. It’s hard to not pin that on Drake. And if we are to give him the credit, we gotta talk about “Marvin’s Room.”

This is the prototypical Drake song. Pensive, muted, soft and loving, but also tough and scathing. He perfectly blurs the lines between what should be sung and what should be rapped. He sings about things most rappers would never commit to record and spits raps that could easily double as what is now referred to as toxic R&B. “Marvin’s Room” shows a dexterity most had never heard before and proved that Drake was indeed an exceedingly special talent. When people clamor for Drake to make an entire album of just R&B cuts, this is the type of music they’re hoping he makes. — DS