Drake and ASAP Mob
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Music

The story of Drake in 10 essential tracks

These aren't just Drizzy's best songs – taken together, they tell the tale of a rapper who remade hip-hop in his own image
Written by Clare Considine
9 min readUpdated on
Nothing about Drake – Aubrey Graham to his beloved mama – fits the hip hop script. He was a teen soap star, talks about his feelings, drinks rosé, he’s…. Canadian? But he can now legitimately count himself amongst the vanguard.
Drake’s breakthrough mixtape, So Far Gone, turned ten last year. Since then he’s released five studio albums, three compilations, six mixtapes and 55 singles. He’s had eight number one albums and outsold his heroes, including Jay-Z, Tupac and Eminem.
Aged 33 he boasts a net-worth of $100 million and counting; three Grammys; grey area relationship histories with both RiRi and Nicki; a clothing brand that succeeds both in being highly profitable and making owls cool; and more American Music Award nominations than Michael Jackson.
Yet, more often than not, Drizzy still ends up the butt of the internet’s favourite jokes.
There’s the sense that he’s someone who takes himself a little too seriously, but lacks the self-awareness to notice that not everyone else is in on the act. However, perhaps comfortable in the knowledge that he’s the top-selling male solo artist of all time in America, he’s also leant into his persona as the ‘Ross from Friends’ of hip hop. The Hotline Bling video alone -- still spawning memes half a decade later -- is evidence enough that perhaps he’s in on the joke after all.
Over the past five years, the Torontonian has expanded his musical palette to take in dancehall, Afrobeats, and harder-edged drill and rap influences. He’s played out a particular obsession with the UK’s music scene: cropping up at a lowkey Section Boyz show; collaborating with Skepta and Giggs; naming up-comers like Loski and Octavian as influences; and dropping a Behind Barz freestyle for UK rap hub LinkUpTV, among other excursions. Responses to his apparent cultural cherry-picking have been mixed. But for all he’s accused of being a culture vulture, his talent, savvy and influence are undeniable.
Drake’s prolific musical output has been relatively quiet for the past few years as Brand Drake has diversified. Last year he turned his midas touch to television, exec producing for two of the year’s biggest hits: Euphoria and Top Boy. But, like a slightly seedy Santa, come last Christmas eve he was ready to drop some new tunes. And just this week he broke (another) new record, with his guest spot on Lil Yachty’s Oprah’s Bank Account making him the artist with the most US chart hits ever (a cool 208). He just can’t stay away….

1. Best I Ever Had

Back in 2009 Drake was known in the public consciousness as the star of Canadian teen drama Degrassi. But then this Valentines-friendly singalong slice of hip hop sweetness landed as lead single from his first bash at the music bizz, So Far Gone. He started dating Rihanna, his track dominated the summer and he proved to be a master of the rap-to-sing segway. Pitchfork didn’t get it: “See, Drake’s not a great rapper. His delivery manages to convey confidence at pretty much all times, but it’s still halting and awkward." But, it seems, the people did. Drake had arrived and hip hop would never be the same again.

2. Marvins Room

The lead single from 2011’s Take Care was too spartan to ever crack the Top 20, but it introduced us to glum in the club Drake. With a seat firmly at hip hop’s top table he was freed up to get creative with his sophomore sound and Drake had clearly been bumping some UK production nerds like James Blake and Jamie xx. Here, with his trusty producer, 40, he brings a smouldering instrumental and splices in genuine voicemails from an ex to soundtrack Drake pining harder than he's ever pined.

3. Hold On, We’re Going Home (feat. Majid Jordan)

This one goes out to the crooners. It will likely always be cited as the ultimate proof for those who believe that Drake’s at his best when he’s singing. The thoroughbred hit from 2013’s Nothing Was The Same will fill any wedding dancefloor for generations to come. His third album found him free to do whatever he damn well liked (he’d just won a Grammy for Best Rap Album), which sometimes meant indulging in some very Drake-y extensive verses of self-pity. Not here though. There’s a faint melancholy reverberating in the corners, but it invites us to sing it out and bury ourselves inside its warmth. That’s why everyone from Blood Orange to Arctic Monkeys recorded covers. After all, what more do any of us want in life than some hot love and emotion?

4. Started From The Bottom

At this point we all know Drizzy’s back story. And so this track – the first single from Nothing Was the Same – lives and dies on a middle class Canadian teen star’s ability to claim a struggle arc with a straight face. Of course he nails it. Drake believes it and so we do too. Whether it’s life on the streets or a Saturday job at Boots, we all have our struggles. This is an aspirational anthem for us all.

5. Know Yourself

With My Woes is the perfect tattoo for any proud sad sack. And “I was running through the six with my woes” is arguably one of pop’s most iconic chorus lines. It perfectly encapsulates what we will call the Drake dichotomy. At face value he’s riding round his home town heartbroken and missing his momma, OD’ed on champagne and one night stands. But in fact WOE is Drake speak for “working on excellence” – shorthand for anybody he respects and considers worthy to be part of his crew. Drake has always yearned for our sympathy and envy in equal measures. On this cut from 2015 mixtape If You’re Reading This It’s Too Late, he achieves his message with impressive economy.

6. Controlla

For better or worse Drake is one hell of a culture vulture. With varying degrees of credit-given, he’s mined the sounds of everything from South African house music to UK grime. But arguably his most inspirational holiday was to Jamaica, which seemingly spawned the lion’s share of 2016’s Views. Large swathes of the album are peppered with Drake doing patois and Unruly-influenced dancehall riddims. Complete with airhorns and a killer Popcaan verse, Controlla is perhaps the best example of Toronto’s finest in his red, gold and green period.

7. Hotline Bling

Stop what you’re doing right now and re-watch the Hotline Bling video. Of course you’ve watched it a million times already. But we guarantee it will still bring you new levels of joy. The air bongo-ing! That head wobble! Drake knew exactly what he was doing when he donned a turtleneck and danced like nobody was watching bathed in neon pink light. That is why he is King of the Internet. 2016 brought us an audio gift that was everything we love to love about Drake wrapped up in one pastel-hued parcel - some heavily plundered source material; the be-moaning of a good girl gone bad; a title made for phone covers; and a universal sonic appeal that will keep the aunties dancing at any wedding.

8. One Dance (feat. Wizkid & Kyla)

In the grand scheme of things 2016 isn’t all that long ago. In terms of the Drake oeuvre it is an age. So let us jog your memory -- One Dance absolutely dominated summer 2016. It was Drake’s biggest hit to date. It could be heard booming from top-down soft tops, seeping from Central Line earphones, dripping with the sweat from club ceilings. With ever-perfect timing Drake followed up the cultural juggernaut that was Hotline Bling with a bubbling summer ditty that drew globally disparate sounds into one giddy embrace of Afrobeats, funky and hip-hop. It served as proof of just how niche Drake can go in his cultural plundering -- sampling a cult 2008 UK funky hit (Kyla and Crazy Cousinz were no doubt surprised to get that call) and guaranteeing UK-wide Drake-mania in the process. Plus, it readied our ears for his follow-up mixtape, More Life, and the endlessly drinkable pina colada joy of Passionfruit.

9. God's Plan

Leave it to Drizzy to re-brand a slightly standard, critically under-achieving track into one of 2018’s most heavily referenced cultural touch points. God’s Plan came from the Scary Hours EP, knocked another Drake track off the top spot in the charts (Nice For What) and earned him a 2019 Grammy for Best rap song. The video finds him morphing into a sort of Saturday night TV presenter; and, of all of Drake’s wealth of Drakeisms, he might have outdone himself with the lyric, “She say ‘do you love me?/ I tell her only partly/ I only love my bed and my momma, I’m sorry”.

10. When To Say & Chicago Freestyle

By mid-2019, when it came to music, Drake looked to be coasting -- focusing instead on TV work, and releasing Care Package, a compilation of old tracks. But this twofer surprise-dropped earlier this month and has all the markings of a pre-album throwaway Drake moment; a space for him to remind us he’s here, he’s still sad and he still has tonnes of cash. Part of the video is shot in Brooklyn’s notorious Marcy Heights; footage of filming day leaked, Papi looking ever so slightly twitchy in his surroundings. There was no way Drake could let this one lie: “That other clip under covers pulled up quick with the iphones out on my life," Drake explained. "I was tryna see what was going on...it was all Marcy love.” Elsewhere in the video he can be found enjoying luxury melon, getting his Uncut Gems on and quietly organising his bricks of cash like a schoolkid tidying his pencil case. So nothing out of the ordinary, then.
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