Drake has come a long way from rolling down the aisles of Degrassi Community School. He left Wheelchair Jimmy far behind and transformed into one of music’s colossal forces, reframing the ideals of success while simultaneously breaking and creating new records. Following 2009’s breakthrough EP So Far Gone, the artist has soared closer to icon territory by unleashing an impressive string of albums, mixtapes and loosies that became woven in social media commentary and led to historic chart runs. His impact is pretty unshakeable at this point, as even his guest features could be a list all on its own. Call him what you want — Champagne Papi, Heartbreak Drake, Drizzy, The Boy, 6 God, Young Angel, October’s Very Own, OVO Records’ CEO — but there’s no denying he’s on his way to G.O.A.T. status.
In anticipation of his pending sixth album Certified Lover Boy, due out tomorrow, we present a ranking of our favorite songs so far.
60. “Passionfruit” (More Life, 2017)
Sure, “Passionfruit” sounds like the nondescript playlist songs we’ve all heard in H&M and Zara dressing rooms. But that’s part of its magic. Drake does accessibility well, drawing in listeners from all backgrounds and ages to simply…vibe. This More Life cut does just that, with its blend of tropical house and R&B (courtesy of British producer and songwriter Nana Rogues) that makes post-long distance heartache somehow sound oh-so-irresistible.
59. “Unforgettable” Feat. Jeezy (Thank Me Later, 2010)
Drake is a huge Aaliyah fan (he even has the late icon tattooed on his back), and he celebrated her legacy early on in his career with “Unforgettable.” Built around a sample of Aaliyah’s cover of Isley Brothers’ ‘70s classic “(At Your Best) You Are Love,” the singer’s signature coos provide a lush backdrop for both Drizzy and Jeezy’s flirty lines.
58. “Over” (Thank Me Later, 2010)
After years of building his name with mixtapes and being part of the Young Money crew, Drake showed he had something to prove with “Over.” The Grammy-nominated lead single of his debut album Thank Me Later showed it was evident the road to superstardom would become crowded as hell: “I know way too many people here right now that I didn’t know last year / Who the f**k are y’all?” Atop a boisterous beat via and Boi-1da and Al Khaaliq, Drake affirms that he has his eyes set on taking over the game. The one thing holding this back is the overt “hashtag rap” that will keep it stuck in the ‘10s era.
57. “Ransom” Feat. Lil Wayne (non-album single, 2008)
Lil Wayne often brings out the best in Drake, and the potential that he initially saw in the post-Degrassi star is highlighted all throughout “Ransom.” Forget a catchy hook, this song is about straight bars. Weezy ultimately takes the lead here, but he gives his mentee the spotlight to show off his talents. This is Drake at his hungriest and we haven’t heard him like this since.
56. “Wu-Tang Forever” (Nothing Was the Same, 2013)
Based on the title alone, you’d think “Wu-Tang Forever” was actually a tribute to the Staten Island rap legends. But the sample of Wu-Tang Clan’s 1997 “It’s Yourz” cut is where the homage starts and ends. This Nothing Was the Same highlight is all about two things that Drake loves to discuss: paranoia and women. The combination of the ghostly sample and the nightmarish piano gives a dark edge to Drake’s sweet croons. The confusion rightfully ended up rubbing the Wu-Tang Clan the wrong way, but one can’t deny the song’s appealing nature. After all, what’s Drake without controversy?
55. “Money To Blow” with Birdman and Lil Wayne (Priceless, 2009)
Drake’s swagger was on a hundred, thousand, trillion on this Young Money mini-posse single, where he intros with a 24-hour champagne diet declaration that showed off just how rich he was becoming. His flow is so smooth that you can almost forgive his bold-faced flexing. And Weezy couldn’t have prophesied it any better: “And we gon’ be alright if we put Drake on every hook.” Since declaring such on “Money To Blow,” the rapper has collected chart-topping features like an Olympian.
54. “One Dance” (Views, 2016)
When Drake wasn’t looking for revenge all summer ‘16, he was taking over the clubs that year with a trio of dancehall-inspired tunes: “Controlla,” his “Work” team-up with Rihanna and “One Dance.” The latter is the weakest of the three, but it still kept waistlines moving thanks to its fusion of dancehall, afrobeats, and the house subgenre of UK funky. Featuring Nigerian superstar WizKid (who collaborated with Drake the year prior on the “Ojuelegba Remix” and later reteamed for 2017’s “Come Closer”) and British singer Kyla, it was both charming and monotonous. “One Dance” topped the charts in the UK, the US, and Canada, once again showcasing the unshakeable appeal of the African diaspora’s genres.
53. “God’s Plan” (Scary Hours & Scorpion, 2018)
What makes Drake a standout rap artist is his ability to create moments within songs whose impact extends beyond the genre. At face value, “God’s Plan” is a typical track for him, stuffed with endless Instagram captions (“Don’t pull up at 6 AM to cuddle with me”) and catchphrases for festival goers to shout back at him (“I only love my bed and my momma, I’m sorry”). But the beauty is in its simplicity, and the formula worked tenfold: “God’s Plan” secured a Grammy for Best Rap Song and topped the Billboard Hot 100 for eleven weeks.
52. “Legend” (If You’re Reading This It’s Too Late, 2015)
2015 found Drake at his peak cocky stage, which is best and brashly displayed on IYRTITL’s “Legend” opener. He calls upon OVO signee PartyNextDoor to strip and flip Ginuwine’s ‘90s classic “So Anxious” into an ambient soundboard for Drake to showcase zero signs of humility. For him to croon “Oh my God, oh my God, if I die, I’m a legend” as passionately as Ginuwine would croon to his lady fans is completely audacious. But when you’ve racked up a near-untouchable stack of accolades before age 30, can you really blame him?
51. “What’s Next” (Scary Hours 2, 2021)
With every passing year, more people want a piece of Drake, whether it’s his personal life or new music. By the time 2021 hit, fans grew tired of Certified Lover Boy’s disappearing act after first teasing it last summer. Ever the troll, he continued to drop one-off singles with no release date in sight. His latest, “What’s Next,” is a heavy dose of sarcasm that’s not so far off from the eye-rolls targeted at the media on 2018’s “Look Alive” (“I’ve been gone since, like, July, n****s actin’ like I died”) and 2011’s “HYFR” (“Do you love this sh*t? Are you high right now?”). Album or not, he’s highly aware of his relevance and will remind you any chance he gets: “I’m on the hot one hundo, numero uno / This one ain’t come with a bundle.”
50. “November 18th” (So Far Gone, 2009)
“November 18th” is an essential Drake track for two reasons: it signifies the date that Lil Wayne officially signed him to Young Money and changed his life forever, as well as showcasing very early on that the rapper was a sonic shapeshifter. The So Far Gone fan favorite combines Drake’s Toronto-derived somber R&B finesse and the gritty chopped-and-screwed sounds that put Houston on the map. Here, over a sample of DJ Screw’s legendary version of Kris Kross’ “Da Streets Ain’t Right” (which in turn samples Biggie Smalls’ “Warning”) from 1996’s June 27 tape, Drake teases what he would soon become known for: a seamless blend of various cultures.
49. “Made Men” with Rick Ross (non-album single, 2011)
Drake and Rick Ross are one of rap’s ultimate pairings, mainly because they love to brag about their wealth and women. Here, they channel their inner mafiosos while casually one-upping each other’s rhymes. Technically this is Ross’ tune, but Drake steals the show when he tops his homie’s “S65, I call it Rihanna / It got a red top, but it’s white like Madonna” bar by gloating: “One of my baddest women ever, I call her Rihanna / But that’s ’cause her name is Rihanna”.
48. “Believe Me” with Lil Wayne (non-album single, 2014)
“He left Rikers in a Phantom, that’s my n****.” Drake never shies away from his admiration for mentor Lil Wayne, but it truly shines on “Believe Me.” One of their many classic collaborations, the pair reflect on their rapid ascension to become rap’s global superstars, with Boi-1da and Vinylz’s bouncy beat growing tenser within the second half as the YMCMB buddies show off some slick wordplay.
47. “Headlines” (Take Care, 2011)
By the time his second album Take Care rolled around, Drake pushed the uncertainty about his position in the rap game aside and asserted himself as The Boy who has his eyes set on taking on the throne. And “Headlines” encapsulates this smug notion. While a majority of Take Care is rooted in somberness, this single is one of its rare upbeat moments that’s a toast to Drake’s accomplishments. But he also slips in a fair warning to his peers that the real is on the rise: “Soap opera rappers, all these n***s sound like All My Children.”
46. “HYFR (Hell Ya F**king Right)” Feat. Lil Wayne (Take Care, 2011)
On “HYFR,” Drake only focuses on his ex-girlfriends just for a moment before finally giving himself the freedom to have fun. Executing a rare double-time flow, both he and Lil Wayne drop catchy bars (“I learned Hennessy and enemies is one hell of a mixture”) before leaning into a sarcasm-dripping chorus over a synthwave guitar. The video makes this even more of a banger, with Drake throwing the dopest bar mitzvah ever.
45. “Jumpman” with Future (What A Time to Be Alive, 2015)
There’s plenty of standouts on Drake and Future’s What A Time To Be Alive joint mixtape, from the former’s shameless outro on “Diamonds Dancing” to Future facing his demons on “Scholarships.” But “Jumpman” was a special one, as Future helped ignite his friend’s inner trap king. What A Time to Be Alive is mainly in Future’s wheelhouse — recorded in Atlanta, executively produced by right-hand Metro Boomin, and is mostly about the city’s grungy hustle — but Drake holds his own as the two join forces like Michael Jordan and Scottie Pippen to create a club-ready banger.
44. “Summer Sixteen” (non-album single, 2016)
Drake had a chokehold on the year 2016, and the takeover began with “Summer Sixteen.” Released that January, Drake (a decorated diss artist at that point) aimed his shots at the heads of Meek Mill and Tory Lanez. The song really revs up in the second half, with a sinister beat anchoring his brags of — what else? — having the biggest pool of any rapper. If his point wasn’t made clear enough, DJ Khaled swoops in on the outro: “They don’t want us to have a bigger pool than Kanye!”
43. “Up All Night” Feat. Nicki Minaj (Thank Me Later, 2010)
Drake may have been putting on for his team on Thank Me Later’s “Up All Night,” but his Young Money labelmate snatched the mic with her monumental guest verse. Drake holds his own on the thumping track, but it ultimately belongs to Nicki Minaj. “If Drizzy say get her, imma get her,” Minaj begins — and that she does, going fully rabid as she pierces haters with taunts and cocky one-liners: “I look like ‘yes’ and you look like ‘NO’!”
42. “Club Paradise” (Care Package, 2019)
Fame often comes with a price, and usually it’s the ones you love who get struck the most. “Club Paradise,” part of the handful of teaser tracks Drake shared prior to Take Care’s release, summates his feelings of leaving his hometown in order to make his dreams come true. Titled after his favorite Toronto strip club, it’s a tale of melancholy, nostalgia, and that signature paranoia as Drake comes to terms with the fact that his old life with nameless strippers, old girlfriends, childhood friends like Chubbs and his beloved mother Sandy has drastically changed. When he raps, “Just lie to my ears / Tell me it feel the same, that’s all I’ve been dying to hear,” you really feel it.
41. “Nonstop” (Scorpion, 2018)
After first teaming with Tay Keith on BlocBoy JB’s 2018 single “Look Alive,” the Memphis producer dug deep into his crates and returned to craft one of Drake’s gnarliest hits. Yet another ode to the Southern city, “Nonstop” utilizes local rap stars Mack Daddy Ju and D.J. Squeeky’s 1995 tune “My Head Is Spinnin’.” The minimalist production is the perfect sounding board for Drake, who opts to flex in a playful and lowkey manner than his usual assertive style. It works to his advantage, flipping the switch to a newfound whispered flow dotted with adlibs that’s so nonchalant you almost forget he’s talking smack.
40. “Cameras / Good Ones Go” (Take Care, 2011)
Man does 40 know how to finesse a sample. On this Take Care duo, the producer flips Jon B.’s 2001 ballad “Calling On You” for a late-night, R&B-inspired melody. You can almost picture Drake sipping on whiskey neat (long before he’d launch his own Virginia Black variety) as he dissects how the media perception can play a role in a celebrity relationship, often inciting disillusions that lead to trust issues. Once “Good Ones Go” kicks in, Drake comes to terms with the fact that he has to let his girl go. The Weeknd’s comforting coos make the task a bit easier.
39. “4pm in Calabasas” (Care Package, 2019)
Drake is just rude on this 2016 loosie, where he emerged from his post-Views Toronto retreat to flex on his enemies while soaking up the California sun. The origins of the Diddy-Drake beef is still cloudy (it might’ve sparked over a bitch slap), but Drake makes it known that he wants the Bad Boy legend to feel the same sting he implemented. The song is just bar after bar of not-so-covert disses, from “Can’t nobody hold me down” to “Make them dance to this.” And he does it all with a wicked laugh, a-ha-ha-ha.
38. “When To Say When” (Dark Lane Demo Tapes, 2020)
Dark Lane Demo Tapes was meant to be a sampler to hold fans over until the release of Certified Lover Boy, quenching their thirst with a mix of new songs, leaked favorites, and SoundCloud staples. “When To Say When” was an immediate standout on the otherwise bland taste test, with Drake heading to Brooklyn’s Marcy Projects as he rhymes over Jay-Z’s The Blueprint classic “Song Cry.” Continuing its vulnerable theme, the rapper unpacks his conscience: “Thirty-three years, I gave that to the game / Thirty-three mil’, I’ll save that for the rain / Five hundred weeks, I’ll fill the charts with my pain.” It’s a therapy session without the insurer’s invoice.
37. “Say What’s Real” (So Far Gone, 2009)
It only made sense that Drake decided to pour his heart out over the instrumental to Kanye West’s 808s & Heartbreak highlight “Say You Will.” But rather than trying to heal a broken heart, “Say What’s Real” is an insight into the mind of a rapper who’s fully aware of his come-up. “Why do I feel so alone?” he begins, before revealing his uncle’s urge to protect his privacy, getting smug about his growing number of ladies, bargaining with major labels and ultimately finding the confidence to dominate.
36. “Ignant Shit” Feat. Lil Wayne (So Far Gone, 2009)
When Drake kicks off a song by introducing himself and Lil Wayne as “Young Angel and Young Lion,” you know it’s going to be a moment. “Ignant Shit” finds the pair skating ever so fluidly over Jay-Z’s American Gangster highlight, where Just Blaze flips Isley Brothers’ 1983 classic “Between The Sheets.” The sample has become an integral staple in hip-hop, and its use can come across as try-hard. But Drake and Lil Wayne make it all their own, shifting away from Jay-Z’s pop culture-referencing aim at rap critics and having fun trading catchy bars.
35. “Feel No Ways” (Views, 2016)
We’ve all been there before: making excuses to stay in a dying relationship that feels more like a tedious cycle than a blissful union. Drake hits on these emotions on this deep cut, whose electro-pop-R&B fusion sounds like it could be plucked right from the ‘80s. Majid Jordan’s Jordan Ullman flips former Sex Pistols’ manager Malcolm McLaren’s “World Famous (Radio I.D.)” into a sparkling gem that gives Drake some sense of clarity. “There’s more to life than sleeping in and getting high with you / I had to let go of us to show myself what I could do.” The song was later given new life, with the rapper performing it at Camp Flog Gnaw in 2019, the biggest highlight of an otherwise shaky set. Even Tyler, the Creator (who founded the festival) couldn’t contain his excitement, later showing admiration for the “beautiful” track on Twitter.
34. “The Motion” (Care Package, 2019)
Sometimes you avoid coming to terms with the fact that a relationship (either romantic or platonic) is no good for you, which is what Drake struggles with on 2013’s aqueous Nothing Was The Same precursor. He can’t rely on friends or his woman, as they both take advantage of his kindness. “The girl that I wanna save is like a danger to my health,” he painfully shares. “Try being with somebody that wanna be somebody else.” Toss in Sampha’s grieving vocals at the end and it just makes the tears well even faster.
33. “Know Yourself” (If You’re Reading This It’s Too Late, 2015)
Drake has utilized the “Know Yourself” phrase before (“Jodeci Freestyle,” “From Time,” “0 To 100”), but on this immediate fan favorite, it soared to hometown anthem status. It begins unsuspectingly, with a brooding flow that matches Boi-1da’s tense production. But as soon as that choral chant begins — “I was. running. through the 6. With my WOES!” — blood rushes to your head as the urge to take over the streets kicks in.
32. “Jungle” (If You’re Reading This It’s Too Late, 2015)
40 has produced a lot of showstopping tracks for Drake, but “Jungle” stands out as one of his most gorgeous melodies. Wrapped around a sample of alt-R&B singer Gabriel Garzón-Montano’s “6 8,” this IYRTITL deep cut is driven by heartfelt nostalgia. Drake has always been a hopeless romantic at heart, and he longs for a past love that he foolishly left behind in Toronto’s rugged Lawrence Heights neighborhood. When he sings, “Hate that I treat it like it’s a ‘whatever’ thing / Trust me girl, this sh*t is everything to me,” it’s clear that he severely messed up.
31. “The Motto” Feat. Lil Wayne (Take Care, 2011)
You couldn’t go anywhere without hearing someone shout “YOLO!” back in 2011. It was all Drake’s doing, as he popularized the phrase with his catchy “The Motto” single. He’s too-cool here, spitting ever so casually on a hyphy-inspired beat (“Rest in peace, Mac Dre, I’ma do it for the Bay”). While he didn’t invent it, the rapper was the reason why “YOLO” skyrocketed into the cultural stratosphere. Once he got hold of it, “YOLO” — or “You Only Live Once” — became way more than just an acronym. It was a complete lifestyle, with people using the literal motto to define their carefree and sometimes reckless “f*ck it” attitude with a shrug.
30. “Hotline Bling” (Views, 2016)
As soon as Drake began hitting those dorky Dad dance moves in his now-iconic red bubble coat in the “Hotline Bling” video, it was evident the song was heading into ubiquity. The Grammy-winning tune is filled with condescending lyrics that men (who have lost the love of their lives due to their silly mistakes) have turned into their personal mantras. From the opening line “You used to call me on my cell phone, late night when you need my love” to the remorseful pain behind “Started wearing less and going out more” and even the song title itself, “Hotline Bling” became a meme-worthy anthem for those who couldn’t get over their old flame.
29. “Duppy Freestyle” (non-album single, 2018)
Drake has been defending himself through diss tracks since the beginning of his career, and on “Duppy Freestyle” he was audibly over it. The sigh that precedes “the nerve, the audacity” intro is near comical Drake-ism, but also gives heavy “please stop playing with me” energy. It was released as a response to Pusha T’s “Infrared” that brought up the same ghostwriting allegations that Meek Mill harped on years prior. You can hear Drake’s exasperation as he tries to lets both Push and Kanye West down easy, from “Father had to stretch his hands out and get it from me / I pop style for 30 hours then let him repeat” to “Don’t be ashamed, it’s plenty n****s that do what you do / There’s no malice in your heart, you’re an approachable dude.” Pusha T later fired back with the mighty vicious “The Story of Adidon,” but let’s be real: Drake’s “Duppy Freestyle” is the one that most still have on repeat to this day.
28. “Lemon Pepper Freestyle” Feat. Rick Ross (Scary Hours 2, 2021)
Drake and Rick Ross bring out the best in each other, and “Lemon Pepper Freestyle” continued that winning streak. Here, over a delicate sample of indie-pop duo Quadron’s 2010 tune “Pressure,” the two do what they do best: balancing their lavish lifestyles with a heavy dose of introspection about their personal lives outside of the awards shows and yachts. Drake, growing more comfortable with rapping about his son Adonis, even throws in a bar about thirsty housewives at the PTA meetings. His lyrics are just as satisfying as the lemon pepper wings the song is named after.
27. “Fear” (So Far Gone, 2009)
One of Drake’s most underrated moments, “Fear” often gets lost in the sea of the rapper’s many introspective tracks. You can almost hear the hesitation in his tone as he grapples with the fact that his life is about to change forever. The girls he once talked to may look at him differently, his beloved uncle will stop messaging him and naysayers will criticize his talents. “Things are just surreal at home / People think I’ve changed just ’cause my appeal has grown and now security follow me everywhere,” he says somberly, revealing his anxieties. “So I never actually am alone, I just always feel alone / I think I’m scared of what the future holds.” Luckily he didn’t have much to worry about.
26. “Jodeci Freestyle” Feat. J. Cole (Care Package, 2019)
Leave it to Drake to spit cocky lyrics on a song that simultaneously pays homage to Jodeci. Initially released as a 2013 loosie, the collaboration marks the second after Drake hopped on J. Cole’s 2010 Friday Night Lights cut “In The Morning.” He and J. Cole compare themselves to the iconic ‘90s R&B group as they reminisce on all the girls they’ve stolen from their enemies. To add a dose of realism, Drake’s father Dennis Graham recalls their road trips from Toronto to Memphis, with Jodeci naturally being Drake’s go-to on the CD player. It’s a wonder how the two rappers haven’t worked together more, as they bring out clever dexterity in each other.
25. “Look What You’ve Done” (Take Care, 2011)
Drake’s at his best when he lets down his walls. On this Take Care deep cut, he brings us into his world, reminiscing on his family struggles like a spoken word performer at a cigarette smoke-filled lounge. Atop a warm piano melody, Drake details his mother’s health problems and his uncle’s support. As soon as his grandmother’s voicemail plays in the outro, you’re already wiping tears away.
24. “From Time” Feat. Jhené Aiko (Nothing Was The Same, 2013)
Aside from his usual go-tos Nicki Minaj and Rihanna, Drake doesn’t collaborate with women often. So it was a welcomed surprise when Jhené Aiko’s delicate vocals provided the backdrop for this languid deep cut. Aiko plays the old flame, calling him out on his flighty ways (“I love me enough for the both of us”) as Drake comes to terms with the fact that he can’t properly handle a relationship. Unfortunately for him, he realized this too late.
23. “Successful” Feat. Trey Songz (So Far Gone, 2009)
Rapping about highs and lows of success is one of Drake’s go-to themes, but “Successful” finds the star at his most aspirational. With early co-signer Trey Songz on the hook, it’s a somber three-part story anchored by Noah “40” Shebib’s heavy bassline. Drake is his usual cocky self on the first verse: “The young spitter that everybody in rap fear.” But things get real on the second, as he recalls crying with his mother in the driveway as they dealt with family and post-Degrassi money issues. A voicemail from his father anchors the third, and Lil Wayne soon emerges just when you think the song is over. Looking back over a decade after its release, a 2009 Drake probably couldn’t fathom just how much his future self would be able to accomplish.
22. “Controlla” (Views, 2016)
Views was marred by messy last-minute changes, from removing Kanye West and Jay-Z from “Pop Style” to replacing Popcaan with Beenie Man on “Controlla.” Luckily for the latter, both the original and final version became the main highlight of Drake’s lukewarm album era. The rapper is a sonic chameleon with a strong passion for dancehall. He excels here, with the Jamaican stars leading the way into a night of slow wines and rum punch.
21. “Best I Ever Had” (So Far Gone, 2009)
Drake immediately established a diehard fandom upon the release of his first big hit, with many first hearing the rap/R&B hybrid in high school or college and trying to figure out if Drake was the one singing or rapping. He was in fact doing both, sharing sweet nothings (“Sweatpants, hair tied, chillin’ with no make-up on”) in two different flows that’ll soon become his signature. Its blend of cheesiness and charm led to “Best I Ever Had” hitting No. 2 on the Billboard Hot 100, his highest peak until “One Dance” topped the chart seven years later. To further prove his star status, he even got Kanye West to direct the video. Drake didn’t necessarily introduce a new formula. But he sure did perfect it, making him a case study for success in the decade to come.
20. “Hold On, We’re Going Home” Feat. Majid Jordan (Nothing Was The Same, 2013)
Back in 2013, it was a rare occasion for Drake to go full-on pop star on us. He executed it well on this groovy ‘80s-inspired single, as he attempts his best Michael Jackson while working his charm on a love interest. The synth-pop melody has a melancholic edge to it, saving it from being too cheesy. The passion was inescapable, with everyone from Blood Orange to Arctic Monkeys covering the tune. It also introduced the world to OVO Sound signees Majid Jordan, who went on to become alt-R&B favorites in their own right.
19. “Take Care” Feat. Rihanna (Take Care, 2011)
Rihanna brings out Drake’s sensitive side, and while most of their collaborations highlight their flirty chemistry, “Take Care” is all about the emotions. Rihanna’s tender vocals anchor the chorus as Drake opts to sing for most of the track, giving an added dose of honesty. Its sample of Jamie xx’s remix of Gil Scott-Heron’s version of “I’ll Take Care Of You” amplifies the relationship’s rollercoaster, with the pounding drums and sparse piano telling the story of pain, hurt, and trust. The end result shows there’s beauty in vulnerability.
18. “Stay Schemin” with Rick Ross and French Montana (Rich Forever, 2012)
Technically this is Rick Ross’ single, but Drake notoriously took the lead here. Their chemistry is unsurprisingly elite here, with Rozay’s gruff verses and French Montana’s slurred presence give Drizzy the perfect alley-oop to execute what many consider to be his all-time best guest verse. Drake goes at Common’s neck, squashing any competition while also providing one of the most iconic one-liners (“Bitch, you wasn’t with me shootin’ in the gym!”) aimed at Vanessa Bryant that he later apologized for.
17. “Trophies” (Young Money: Rise of an Empire, 2014)
“Man, this sh*t is not a love song” Drake shouts on “Trophies,” making it clear that he’s not always about romance. No, this is the ultimate “Get with the winning team!” anthem, with the rapper’s voice going up a few octaves as he unleashes boastful declarations. As soon as those horns (borrowed from 1994’s Western film Oblivion) start blaring, you’ll get the confidence boost you need to either “f*ck a stripper on the mink rug” or “pop some f*cking champagne in the tub.” But when you’re winning this big, you can choose both.
16. “I’m On One” with DJ Khaled, Rick Ross and Lil Wayne (We The Best Forever, 2011)
“I’m just feeling like the throne is for the taking — watch me take it,” Drake declares on this masterful posse cut. Whether or not he was taunting Jay-Z and Kanye West (he claims that wasn’t the case), he made it known that he wanted to overthrow anyone in his path. Drake lends his voice on the hook and the opening verse, laying the groundwork for Rozay and Weezy to bulldoze. But the song could’ve done with at least one more verse from The Boy. And Drake couldn’t let go of the feeling: a month later, he used the hook to record a softer R&B version that’s best suited for the bedroom after leaving the club.
15. “6PM In New York” (If You’re Reading This It’s Too Late, 2015)
“28 at midnight, wonder what’s next for me,” Drake ponders on the third installment of his AM/PM series, which finds him throwing subliminals nearly as slick as his predecessor Jay-Z. He actually references Jigga man here, confidently expressing that The Throne (a.k.a. Jay-Z and Kanye West) needed to make room for a third legend-in-the-making. Drake states that “‘Best I Ever Had’ seems like a decade ago,” and it really does: following his breakthrough single, he’d become even more confident in his lyricism. The sneak disses are the best part, with Tyga getting caught in the crossfire: “You need to act your age and not your girl’s age”). “It gets worse by the annual / My career’s like a how-to manual, so I guess it’s understandable,” Drake assesses on “6PM In New York,” making it the perfect way to end an album that shared a grim tale of paranoia, cockiness, and post-coitus hopelessness.
14. “Crew Love” Feat. The Weeknd (Take Care, 2011)
The Weeknd’s gloomy, drug-fueled take on Toronto sent shock waves in R&B thanks to his breakout mixtape, 2011’s House Of Balloons. So it only made sense that Drake, who was growing wearier of his surroundings, would gravitate towards his sound. The pair officially joined forces on “Crew Love”, a celebration of the industry rise of their respective OVO and XO collectives. “House Of Balloons was actually supposed to have more songs than it does,” The Weeknd later revealed in 2013. “I had so many records left, and then Take Care came through. ‘Crew Love,’ ‘Shot for Me,’ and ‘The Ride’ were supposed to be on House Of Balloons.” Shoutout to The Weeknd for being so gracious.
13. “Lord Knows” Feat. Rick Ross (Take Care, 2011)
There’s only one way to describe “Lord Knows”: triumphant. Drake calls upon the legendary Just Blaze to craft one of his most spine-tingling melodies that is a stark, refreshing contrast to 40’s minimal beats. The track feels even more heavenly once the gospel choir’s wails kick in, giving Drake and Rick Ross an incentive to flaunt as the former explores his growing status in the rap game. You could almost hear the smirk behind the microphone as they stepped away, knowing they just made a classic. “I changed rap forever,” Drake boasts. He definitely knew.
12. “Started From The Bottom” (Nothing Was The Same, 2013)
“Started From The Bottom” was Drake’s version of the classic rags-to-hip-hop-riches story, reflecting on his career trajectory while calling out critics who question his so-called struggles. While he arguably didn’t actually start from the bottom (this is a former Degrassi star, let’s be real), the song resonated with those who came from humble beginnings. “Started” grew into an anthem about success that fans chanted at parties and wrote in their Twitter bios. It was a reminder to follow your dreams while keeping your day one’s close.
11. “Energy” (If You’re Reading This It’s Too Late, 2015)
Drake became jaded by 2015, and he was fully aware of his rap dominance and how many wanted to throw him off the throne. He throws daggers at his adversaries throughout “Energy,” from family members to groupies to rap peers. “I got rap n****s that I gotta act like I like / But my acting days are over, f*ck them n****s for life.” Needless to say, Drake was fed up. The only thing unclear at the time was Drake’s main target, but he notoriously made that well known in the coming months. Sorry, Meek.
10. “Too Much” Feat. Sampha (Nothing Was The Same, 2013)
Drake has never shied away from detailing his personal life, but “Too Much” took it to a deeper level. He ripped off the curtain that previously hid the growing tension within his family, with Sampha’s soulful hook used as a salve to somehow ease the pain. But Drake can’t hold it back any longer, his voice tightening up as he goes in on the second verse: “Money got my whole family going backwards / No dinners, no holidays, no nothing” and “I hate the fact my mom cooped up in her apartment / Telling herself that she’s too sick to get dressed up and go do shit.” When he says he didn’t sign up for this, you almost question if he’s willing to throw it all away for the sake of maintaining his sanity.
9. “Do Not Disturb” (More Life, 2017)
Also referred to as “7 AM In Germany”, this More Life cut is an unofficial entry in Drake’s “AM/PM” series. It has all the elements we love: sneak disses (the Tory Lanez-directed “You overnight celebrity, you one day star”), introspective and free-flowing rhymes (his mindset while recording Views is telling), and a distorted R&B sample (Snoh Aalegra’s 2017 “Time”). Similar to “6PM In New York” closing IYRTITL in a confident manner, “Do Not Disturb” closes the party track-heavy More Life with pensive thoughts. “Taking summer off, ’cause they tell me I need recovery / Maybe gettin’ back to my regular life will humble me / I’ll be back 2018 to give you the summary,” he revealed in the closing lines. We all need a break sometimes.
8. “Pound Cake / Paris Morton Music 2” Feat. Jay-Z (Nothing Was The Same, 2013)
Drake and Jay-Z’s third collaboration, following 2009’s “Off That” and 2010’s “Light Up,” is their most luxurious. It’s the perfect champagne toast to close Nothing Was The Same, serving as a congratulatory moment for Drake not only securing yet another team-up with his idol, but also matching his lyrical finesse while reveling in the fact that he’s the new leader of rap’s new generation. “Nothing was the same, dawg,” he assures on the song’s final moments. And nearly a decade later, it’s foolish to argue otherwise.
7. “Tuscan Leather” (Nothing Was The Same, 2013)
“How much time is this n**** spendin’ on the intro?” Six minutes and six seconds, to be exact. 40 and Boi-1da try their hand at chipmunk soul, evoking the energy of the Roc-A-Fella glory days with a high-pitched sample of Whitney Houston’s “I Have Nothing.” Drake uses every crevice of the mutating production to his advantage, rapping with a newfound confidence following the glowing release of Take Care. In the same breath, he has nothing else and so much left to prove to the world. He knew it too: “This is nothing for the radio, but they’ll still play it though / ‘Cause it’s that new Drizzy Drake, that’s just the way it go.”
6. “5 AM In Toronto” (Care Package, 2019)
Drake began his “AM/PM” song series with 2010’s “9 AM in Dallas,” thus kicking off a selection of introspective longform raps attributed to wherever his mindset happened to be during a specific timezone. “5 AM In Toronto,” released ahead of 2013’s Nothing Was The Same, is a warning shot as he fully settles into his arrogance while calling out the entire rap game. “Give these n****s the look, the verse, and even the hook / That’s why every song sound like Drake featuring Drake,” he spits, fully settling into the villain role that peers placed him in. He even smokes a blunt in the video just for the hell of it (something he rarely did in public at the time), proving that he was on another level.
5. “Nice For What” (Scorpion, 2018)
As the superstar entered his 30s, he began writing his previous wrongs of lyrical gaslighting by crafting an empowering anthem specifically for women. Released at the height of the #MeToo movement, “Nice For What” captured women’s frustrations with a society that didn’t support us: “You gotta be nice for WHAT to these n***as?” Laid atop a New Orleans bounce-inspired beat, with Big Freedia’s in-your-face adlibs and Lauryn Hill’s “Ex-Factor” sample coursing throughout, “Nice For What” reminded us to hold our chin up, shake our ass if we felt like it and raise a glass to post-relationship liberation. The female-directed video further cemented this notion with appearances from Olivia Wilde, Issa Rae, Tracee Ellis Ross, Tiffany Haddish, and more. We were now unapologetically free. And Drake genuinely admired us from the sidelines.
4. “0 to 100 / The Catch Up” (non-album single, 2014)
Drake wasted zero time setting the tone for this one: “F*ck being on some chill sh*t.” From there, he goes in, unleashing bar after bar discussing everything from his deadbeat father, 40’s health issues, his bevy of groupies, and that signature cockiness (“I been Steph Curry with the shot / Been cooking with the sauce, Chef Curry with the pot, boy / 360 with the wrist, boy”). After leaving you in a headspin, he catches his breath in the second half and calmly details how he and his crew will continue to rule the upcoming year. He stuck to his word, surprise-dropping the If You’re Reading This It’s Too Late chart-topper.
3. “Marvins Room” (Take Care, 2011)
“Are you drunk right now?” says the woman on the other end of the phone. And he is absolutely buzzed. Gone off endless cups of rosé and XO, Drake feeds into his simp mode as he tries and fails to win a former flame back. This is quintessential Aubrey at the core, drowning himself in self-imposed sorrows while still managing to be annoyingly pretentious: “I’m just saying you can do better.” “Marvins Room” reflects every dude who knows they did wrong, but still drunkenly scrolls through their ex-girl’s Instagram stories and sends her half-assed, heart emoji-filled DMs filled with empty apologies. Something about that fragile relatability is the reason why the artist continues to stand out among his peers. He isn’t called “Heartbreak Drake” for nothing.
2. “Back To Back” (non-album single, 2015)
“Diss me and you’ll never hear a reply for it,” Drake maintained on So Far Gone’s “Successful.” Well, he obviously hasn’t been a man of his word, and we’re oh-so grateful for it. Leave it to Drake to pull off scoring a Top 40, Grammy-nominated diss song, which is the better half of “Charged Up.” Aiming for Meek Mill’s head, he got oh-so flagrant with literal back to back insults, from “Is that a world tour or your girl’s tour?” to “Trigger fingers turn to Twitter fingers / You getting bodied by a singing n****.” “Back To Back” is one of the millennial era’s best diss tracks, not just because of the lyrical shots, but what it meant for hip-hop’s social media generation. Similar to how Jay-Z put Mobb Deep’s Prodigy on the Summer Jam screen while performing “Takeover” in 2001, Drake opted to share viral memes during 2015’s OVO Fest headlining set. It was equally scathing and hilarious, a formula that’s still being replicated to this day.
1. “Worst Behavior” (Nothing Was The Same, 2013)
“SH*T!” Not the song you expected, right? Well, you have to travel back a few years to fully get the picture. It’s 2013 and Drake was completely fed up with everyone underestimating his skills as a rapper, with most branding him as too soft, sensitive, or corny. He brilliantly transformed that vitriol into furious gold. The tune purposefully skips, distorts, and bends its back so far that it’s almost tormenting to listen to — but that’s the genius of it. Drake gets absolutely manic in a way that we’ve never heard him before, yelling into the microphone as he channels Eminem’s signature anger: “They used to never want to hear us, remember?/ Motherf*cker never loved us, REMEMBER? MOTHERF*CKER!” He really hasn’t let up since “Worst Behavior,” doing everything from breaking chart records, earning more Grammy wins, getting into multiple kinds of beef and winning (depending on who you ask), becoming a dad and successful businessman. But he did predict that all of this was coming. Remember?
