With 20 more hookless, State of the Union addresses

Over the past decade, Drake has cemented his status as hip-hop’s shapeshifter thanks to a genre-bending catalog of hits. As a result, rap fans have spent the last nine or so years debating which Drake is the best Drake.

Is it Pop Star Drake, who’s responsible for an endless array of timeless hits like “Hold On, We’re Going Home,” “Hotline Bling,” “One Dance,” and “In My Feelings”? Is R&B Drake the one, who, as the King of Petty, turned breakup songs into personal therapy sessions with tracks such as “Marvins Room,” “Take Care,” “Jungle,” and “Redemption”? Maybe Braggadocious Drake is your guy, who’s recorded a handful of the best rap anthems in recent memory, notably “Started From the Bottom,” “Worst Behavior,” “Know Yourself,” and “Back to Back.”

Those are all viable options, but Introspective Drake is quintessential Drake. He rapped “I made a career off reminiscing” on Views’ third track, “U With Me?" because no rapper is better at crafting reflective masterpieces. An essential part of the Confessional Drake canon is his trademark AM-PM series, a four-song set that charts the course of his career, with each track representing a different stage in the development of Drake’s character.

“9AM in Dallas” arrived when Drake was on the brink of superstardom, three days before the June 2010 release of his debut album, Thank Me Later. “5AM in Toronto” was a warning shot to rivals delivered in the wee morning hours of March 7, 2013, six months before he claimed hip-hop’s top-spot with his third album, Nothing Was the Same. “6PM in New York,” the outro to Drake’s February 2015 "mixtape" If You’re Reading This It’s Too Late, was a subliminal-soaked flex that foreshadowed the following summer’s beef between him and Meek Mill. Finally, in June 2016, just one month after Views was met with lukewarm reviews, Drake responded with “4 PM in Calabasas,” a four-minute reminder that he was still king.

Of course, the AM-PM series is merely a subset of the extensive collection of state of the union addresses peppered throughout Drake’s catalog. It’s time we expand the series by selecting one hookless Drake song for each hour of the day.

“12AM in Houston” (“No Tellin’,” If You’re Reading This It’s Too Late, 2015)

The first three minutes of “No Tellin’” is a half-assed flex about how Drake’s rolling in dough in all kind of ways—lump sum and residual. But then the beat switches up, a distorted gospel refrain kicks in, and he takes us to church. Backed by deflating synths, the final two minutes find Drake contemplating his legacy, how far he’s come, and what heights he has yet to reach.

The length of his dominant run atop hip-hop sets in when he transports us back to Houston. In the same city where, six years earlier, he was introduced to the lifestyles of hip-hop’s rich and famous, Drake is now the living legend who’s forced to eat his Alfredo pasta in the kitchen of VLive like a mob boss. Then, as if we weren’t aware, he takes a moment to remind us that this isn’t 2011, back when he still had his eyes fixated on the throne. “Please do not speak to me like I’m that Drake from four years ago / I’m at a higher place.”

Of course, the most profound statement comes at the beginning of his final verse, when Drake practically foreshadows the beef that would, five months out, threaten to end his reign. “I gotta keep watching for oppers, ‘cause anything’s possible, yeah / There’s no code of ethics out here, anyone will take shots at you, yeah.” More impressively, the next line suggests that even Drake knew he was too big to fail, as he shrugs off Meek’s future shots, rapping, “N****s think they can come take what I got / Let’s be logical, yeah.”

“1AM in Napa Valley” (“The Ride,” Take Care, 2011)

“The Ride” wasn’t the first time Drake grappled with the trappings of fame. By then, he’d mulled over the idea on a handful of songs. But, whereas on So Far Gone’s “Say What’s Real” and his 2010 loosie “Paris Morton Music” he remains optimistic while facing the pressures of celebrity brought on by his sudden rise, Take Care’s closing statement finds him trepidatious and jaded.

On “The Ride,” Drake delivers the first two verses in the second person, arguing that us mere mortals can’t understand how his success has him feeling so alienated. On the first, he details his current situation of fame and fortune, rapping from his new place atop the throne (“You won’t feel me until everybody say they love you, but it’s not love / And your suit is oxblood / And the girl you fucking hates you, and your friends faded off shots of / What you ordered to forget about the game that you on top of”), a position worthy of dinners at French Laundry in Napa Valley, where the maître d' treats you like a king and puts the cloth across your lap as soon as you sit down.

On the second verse, Drake takes listeners back to his pre-fame days, a time when he would steal his mom’s debit card and drive around in overpriced rental cars just to maintain an image. He looks back on his pre-rap stardom fondly with lines like “You know it’s real when your latest nights are your greatest nights / The sun is up when you get home, that’s just the way of life.”

And then, in the final verse, he switches back to the first person and, suddenly, he’s hostile, concluding the best album of his career with a warning shot. “You n****s getting older, I see no threat in Yoda / I’m out here messing over the lives of these n****s that couldn’t fuck with my freshman floater / Look at that fucking chip on your nephew's shoulder / My sophomore, I was all for it, they all saw it / My junior and senior will only get meaner, take care, n***a.

“2AM in Los Angeles” (“The Catch Up,” 2014)

After snatching the crown in September 2013 with his third studio album Nothing Was the Same, Drake operated on cruise control during the first half of 2014, ringing in the new year with back-to-back bangers (“Trophies” and “We Made It”), before offering up a pair of superb one-offs that spring (“Days in the East” and “Draft Day”). His official return, though, came on June 1, 2014, when hip-hop’s prince-turned-king posted “0 To 100 / The Catch Up” to OVO’s SoundCloud page.

Initially, “0 To 100” received all the attention and for good reason: it was the catchiest Drake song in recent memory and the best rap anthem of the year. Still, the second half of the two-part track, “The Catch Up,” resonated on a much deeper level, as Drake addressed rivals from his newfound place atop the throne.

It wasn’t the first time he declared himself alpha dog of the rap game, but it was the first time he was right. By then, the only question worth asking was where Drake ranked on the list of all-time greats, something he was beginning to wonder himself as evidenced by lines like “Headed where nobody too it / Who meeting me there? / They tell him that he’s talking crazy but he doesn’t care / Being humble don’t work as well as being aware.”

It’s easy to imagine Drake delivering the verse from his estate in the hills above Calabasas, looking out at the glimmering lights of Los Angeles while plotting the next act of his career. “'Cause I’m only 27 and I’m only getting better / If I haven’t passed you yet, watch me catch up now.

“3AM in New Orleans” (“Duppy Freestyle,” 2018)

In hindsight, “Duppy Freestyle” is almost single-handedly responsible for inspiring Pusha T to deliver his knockout blow on “The Story of Adidon.” Still, it’d be irresponsible to remember “Duppy” as merely a footnote to the most shocking diss track in recent memory. Sure, it pales in comparison to “Back to Back,” but “Duppy” is a strong song nonetheless.

Backed by a saxophone loop that sounds like Kenny G is performing at an after-hours New Orleans jazz club, Drake’s opening words set the stage for his subsequent superb performance. “I’m in shock. The nerve. The audacity.” From there, he’s off and running, questioning Pusha’s disses on “Infrared” that degraded him for using ghostwriters by calling out Pusha’s boss, Kanye, for having Drake write verses on The Life of Pablo.

After sending shots at Pusha (“You’re not even top five as far as your label talent goes”), Drake targets Kanye’s insecurities as a wannabe fashion mogul by painting his ex-idol out to be a jealous parasite, rapping “I could never have a Virgil in my circle / And hold him back 'cause he makes me nervous / I wanna see my brothers flourish to they higher purpose / You n****s leeches and serpents / I think it's good that now the teachers are learnin'.

In the final frame, Drake directs his attention back to Pusha, once again berating him for exaggerating his drug dealing past before addressing his career decline by owning up to the signed Clipse-era microphone Drake bought years ago on eBay (“I once had a microphone of yours, but then the signature faded / I think that pretty much resembles what’s been happening lately”) and clowning Pusha for being older than his boss (“I really shouldn’t have given you none of my time / ’Cause you older than the n***a you runnin’ behind”).

Of course, the lyrics that will be remembered for the rest of Drake and Pusha’s careers come later, when the former mimics the latter’s flow and name-drops his fiancé (“I told you keep playin’ with my name and I’ma let it ring on you like Virginia Williams”), unknowingly walking into a bear trap that would culminate in an almost-career-ending reveal for Drake.

“4AM in Hidden Hills” (“Jorja Interlude,” More Life, 2017)

In 2012, Drake purchased a three-acre compound in Hidden Hills, California, a gated community located up the road from the Kardashian-ruled village of Calabasas. Since then, the 7,500-square-foot estate has doubled as a character in Drake’s music, featuring a home studio, where Nothing Was the Same and its successors were recorded; a pool, where naked women swim (“Furthest Thing”) and parties resemble Mardi Gras (“U With Me?”); tennis courts, where he beat a playing-left-handed Serena Williams (“Worst Behavior”); and a basketball court, where the Golden State Warriors practice (“Summer Sixteen”).

It’s obvious that Drake’s home doubles as a bachelor pad for his entourage, a man-child’s amusement park stocked with an endless supply of bikini-clad women, alcohol, and weed. So what happens when the parties end, his cronies head back home, and the booty calls go unanswered? You’re left with a 32-year-old Peter Pan.

With this in mind, it’s easy to imagine Drake recording “Jorja Interlude” isolated in his empty estate high above Los Angeles. He sounds as irritable as ever, and you can sense his fatigue as soon as he opens the track rapping “Told me I’m looking exhausted, you hit it right on the nose / I’m tired of all of these n****s, I’m tired of all of these hoes.”

“6AM in Las Vegas” (“Over My Dead Body,” Take Care, 2011)

On November 7, 2011, during the twilight of the pre-Instagram era, before scheduled release dates were abided by and hip-hop’s blockbuster albums arrived at the crack of midnight via streaming giants Apple Music and Spotify, Take Care sprung a leak. Drake’s sophomore LP hit the internet accompanied by insurmountable expectations, largely because every millennial hip-hop head had cemented it an instant classic as soon as he sent warning shots to rivals earlier that summer on “Dreams Money Can Buy” and “I’m On One.”

Alas, the first lines of Take Care were powerful enough to erase any sense of doubt. “I think I killed everybody in the game last year, man, fuck it, I was on though,” raps Drake, behind 40’s airy production, a distorted piano loop, and an eerie hook sung by Canadian singer-songwriter Chantal Kreviazuk.

From the jump, “Over My Dead Body” didn’t just feel like the perfect opener for his first classic album. It was also the beginning of the Drake Regime. Even he could sense it, opting to take a victory lap on track one, particularly near the end of the second verse when he delivers the final lines with complete confidence: “Feel like I been here before, huh? / I still got 10 years to go, huh?

Could you blame him? By then, Drake had been plotting his coronation for awhile; “Over My Dead Body” was just the first moment it was real.

“7AM in Amsterdam” (“Do Not Disturb,” More Life, 2017)

Across every Drake project, the final track is his closing statement, a space that finds him at his most introspective. Drake treats each outro like a public service announcement—reflecting on how far he’s come while looking ahead to the heights, if any, he has yet to reach. The shoulder chip noticeably absent on Views returned on More Lifes curtain call, “Do Not Disturb.” The heart-wrenching sample (courtesy of Boi-1da) brought back “The Ride” vibes, setting the stage for Drake to come correct.

Over three-plus minutes, Drake reflects on the backlash following his last release, but not before reminding us of his spotless resume (“I’d probably self-destruct if I ever lose, but I never do”); he foreshadows the personal news that would accompany his next album rollout; then, finally, he teases his return (“Takin’ summer off, ’cause they tell me I need recovery / Maybe gettin’ back to my regular life will humble me / I’ll be back in 2018 to give you the summary”).

“8AM in Harlem” (“Tuscan Leather,” Nothing Was the Same, 2013)

How do you follow up one of the best album openers in hip-hop history? Take a Whitney Houston sample, inject it with steroids cut from the same cloth as the chipmunk-soul sound popularized in the early-2000s by Kanye, Just Blaze, and the Heatmakerz, then rap as if your life depended on it—for three consecutive verses.

"Tuscan Leather" starts with 40’s hall-of-fame production. While similar to the chirping vocal loops the Harlem-bred Heatmakerz trademarked on the Diplomats’ “I’m Ready,” 40 raises the stakes: sampling one of the most recognizable songs from the biggest female pop star of the ‘80s—Whitney Houston’s “I Have Nothing—speeding it up and reversing it, before flipping it three different times to create three distinct beats.

Of course, production this monumental would’ve been all for naught if Drake hadn’t brought his A-game. And boy, did he ever. Drake matches every 40 switch-up with a completely different flow and mood. On the first verse, he’s confident, on the second, he’s defiant, and on the closing frame, he’s introspective (“Wanted to tell you accept yourself / You don’t have to prove shit to no one except yourself”). It all amounts to arguably the best song in Drake’s discography, one that makes every hookless freestyle of his inferior by default.

“10AM in Jackson Hole” (“March 14th,” Scorpion, 2018)

When Scorpion dropped, album closer “March 14th” was taken to be a defensive response to Pusha-T’s “The Story of Adidon.” However, according to many producers involved in the making of “March 14th,” the song was written and recorded well before Pusha outed Drake for hiding a child. In fact, according to Drake, “March 14th” is actually responsible for “The Story of Adidon,” given that he played Kanye an unfinished recording of the track while visiting West in Jackson Hole, Wyoming.

If this is true, it’s too bad we’ll never know how “March 14th” would’ve been received had it been how Drake revealed his kid to the world, even if, instead, we were blessed with one of the most jaw-dropping diss songs in hip-hop history. Still, if you can forget everything you knew before you first heard “March 14th,” and listen to it now, it resonates on an entirely different level.

Just imagine the alternate reality where, on the closing track to the biggest commercial album of his career, Drake drops his son on us in the opening lines, rapping, “Yesterday morning was crazy / I had to come to terms with the fact that it’s not a maybe / That shit is in stone, sealed, and signed / She not my lover like Billie Jean, but the kid is mine.”

“11AM in London” (“Draft Day,” 2014)

Four and a half years ago, Drake had a 100-percent approval rating, Johnny Manziel was fresh off becoming the first Heisman winner to rock an OVO tattoo, the money sign was being tossed around like a gang sign on every Instagram post by the 6 God and his minions, Kansas freshman and Toronto native Andrew Wiggins was a poor man’s Zion Williamson, Chance the Rapper was largely unknown, and hip-hop talking heads were still trying to make JAY-Z vs. Drake a thing.

All of these forces collide on “Draft Day,” a slick-talking flex with more pop culture references than any song in the Drake canon. Released on April 3, 2014, while he was in London for the final leg of his third headlining world tour, the track signaled the beginning of an eight-month stretch where Drake dominated 2014 without ever releasing an album.

Over a sample of Lauryn Hill’s “Doo Wop (That Thing),” Drake opens the track sounding as confident and loose as he ever has, rapping, “Sometimes I laugh with God about how you can’t stop me / I’m his darkest angel, probably, but he still got me.” From there, he’s off and running, sending stray shots at then-up-and-comer Chance, directing subliminals at Hov, and touching on everything from his Sprite endorsement and love for Jennifer Lawrence to dining with Qatar royals and eating raw oysters. The verse may be braggadocious, but Drake’s charisma has you rooting for him the entire time.

“12PM in Oakland” (“Two Birds One Stone,” 2016)

While performing in the Bay Area days before his 30th birthday, Drake took to OVO Sound Radio to announce his forthcoming project, More Life, and release a string of new records: instant radio hit “Fake Love,” brooding 21 Savage collaboration “Sneakin’,” and scathing diss “Two Birds One Stone.”

On the track, Drake sends various shots at G.O.O.D. Music, first insinuating that Pusha T exaggerates his drug-dealing past (“But really it's you with all the drug dealer stories that's gotta stop, though / You made a couple chops and now you think you Chapo”), before mocking Kid Cudi’s struggle with mental illness. The Boy stoked the fire, to say the least.

In hindsight, it’s ironic that the song which led to Pusha T vocalizing Drake’s parents’ marital issues on “The Story of Adidon,” finds Drake discussing their divorce, as he does on “Two Birds and One Stone, rapping, “More blessings for Sandi and him, more life / My parents never got it right / God bless 'em both, I think we all alike / We all wide awake late at night / Thinking on what to change if we do get to do it twice in another life.”

Eerily, two years later, Drake was the one left wondering what could have been had he not poured gasoline on an already simmering fire between him and Pusha T.

“1PM in Scarborough” (“Summer Sixteen,” 2015)

On January 30, 2016, moments after announcing an April release date for Views, Drake dropped promotional single “Summer Sixteen.” Compared to previous warning shots delivered leading up to the release of Thank Me Later (“9AM in Dallas”), Take Care (“Dreams Money Can Buy”), and Nothing Was the Same (“5AM in Toronto”), “Summer Sixteen” was a call to arms. It finds Drake on the offensive, sending direct shots at recent victim Meek Mill and not-so-subliminal subliminals at up-and-coming Toronto artists, specifically Tory Lanez.

Produced by 40, Boi-1da, and CuBeatz, “Summer Sixteen” is all hammering bass and Drake venom, perfectly encapsulating the icy vibe of a frigid winter in Toronto. The 6 God delivers both verses cooly yet villainously as if he’s riding shotgun while parading around back streets of the rougher side of Toronto, specifically Scarborough, a West Indian community located in the city’s east end, which he shouts out in the opening lines with reference to Pitfield Road.

The song's first half serves as Drake’s closing argument in his ongoing case against Meek Mill, as he follows the previous summer’s one-two punch of “Charged Up” and “Back to Back” by dancing on his enemy’s grave. After the beat switches up midway, Drake turns his attention to the Six, reminding the city’s stable of rising talent who they’re indebted to, rapping, “All you boys in the new Toronto want to be me a little / All your exes know I like my Os with a V in the middle / You would love it if I went away or didn’t say nothing else / How am I keeping it real by keeping this shit to myself?

As always, no enemy or doubter was left unscathed.

“2PM in West Hollywood” (“Dreams Money Can Buy,” 2011)

Before he would take shots at the throne on “I’m On One,” before he became the first artist to craft a drunk-dialing masterpiece with “Marvins Room," and before Take Care became one of the most significant rap albums for a generation, Drake marked his return with “Dreams Money Can Buy,” a one-off loosie posted to his OVO blog page on May 20, 2011. More than anything, it was a warning shot, both to his rivals and doubters: the question was no longer if, but when Drake would lay claim to hip-hop’s top spot.

40’s production embodies the bristling ambiance that would go on to define Drake’s forthcoming magnum opus, as the Boy assesses his ascension into the upper echelon of the rap game. This isn’t the rookie who sounded uncomfortable on Thank Me Later; instead, he’s frosty, delivering both verses as if he’s comfortably reclined while his driver speeds down Sunset Boulevard in West Hollywood, the site of Marvin Gaye’s famous studio, Marvin’s Room, where Drake, while away from Toronto, had bunkered down to begin recording Take Care.

“3PM in the Cayman Islands” (“We Made It Freestyle,” 2013)

Immediately after releasing Nothing Was the Same, Drake embarked on his third headlining tour, Would You Like a Tour?, spending the rest of 2013 promoting the very album that made him king. Then, two weeks after the tour wrapped in Philadelphia on December 18, 2013, he returned with his first post-Nothing Was the Same offering, “We Made It.” Leaked on December 28, the loosie soundtracked whatever debauchery you participated in on New Year's Eve that year, most likely looking like an idiot while yelling “WE MADE IT!”

The track was the perfect celebratory send-off to the then-defining year of Drake’s career, arriving at a moment when his approval rating was at 100 percent. Never one to shy away from beating his chest, Drake takes bravado to the extreme on “We Made It,” yet you never doubt his sincerity for a second, even as he ratchets up the douchebaggery on cringe-worthy lines like “She said she working for Walgreens but not at the store at the head office / The head was so good it makes sense why you work at the head office.” In typical Drake fashion, he makes you feel like the coolest motherfucker alive without having to put forth much of an effort.

“5PM in Weston” (“Weston Road Flows,” Views, 2016)

Five minutes into Views, you could sense that something was off with the album. After kick-starting his previous two LPs with stellar openers, “Over My Dead Body” and “Tuscan Leather,” Drake went left with “Keep the Family Close,” a song that was more whiny ballad than earth-shattering intro. Drake remains bitter and lethargic until track six, which amounts to one of the most nostalgically gorgeous cuts in his catalog.

For an album that doubled as an ode to his hometown, there was no song more fitting to open the LP than the Mary J. Blige-sampled “Weston Road Flows.” It all starts with 40, whose dreary production captures what it feels like to drive through a cold weather city during December, those freezing, early winter days when daylight is fleeting and the sun sets before five o’clock.

Backed by 40’s atmospheric beat, Drake reflects on his hometown for four straight minutes, sounding as comfortable as ever and for good reason: for a rapper who’s made a career off ‘90s R&B samples, this was as polished as any in his catalog. In short, “Weston Road Flows” is the sound we thought we’d get as soon as the album’s cover displayed Drake sitting alone atop the CN Tower; even if it was only for a song, the feeling is everlasting.

“7PM in Brooklyn,” (“Pound Cake / Paris Morton Music 2,” Nothing Was the Same, 2013)

If you remain unconvinced that Drake knew Nothing Was the Same would serve as his official coronation, look no further than the tracklist. You think it’s coincidental that the album’s only rap feature is none other than the GOAT? Or that Drake randomly slotted the JAY-Z-assisted “Pound Cake” as the first half of the LP’s two-part closer? Please. It was all part of Drake’s calculated master plan, which would culminate with a torch-passing moment on Nothing Was the Same’s curtain call. Five years on, it still remains a moment.

When the two rap giants linked up on “Light Up,” a deep cut off Drake’s 2010 debut, Thank Me Later, it felt like a disingenuous teacher-mentors-student learning lesson, as JAY-Z gave the rookie advice on the wicked ways of showbiz, rapping, “Drake, here's how they gon' come at you / With silly raps for you trying to distract you  / In disguise, in the form of a favor.” Three years later, though, Drake was no longer looking up at his idol; by 2013, he had firmly cemented his place at the big boy table, a reality he reaffirms while bodying Jay on the outro’s first half.

Yet, while “Pound Cake” is the more iconic of the two parts, the closer’s second half, “Paris Morton Music 2” is when Drake ascends the throne. He opens his sprawling, 32-bar verse, informing listeners that he’s done apologizing for passing up his idols before he revisits every critique that’s been thrown at him by his predecessors.

The highlight of the track, though, comes in the last sequence, when Drake, after reflecting on meeting Lil Wayne for the first time in 2008, ends the biggest album of his career with a Peak Drake, unapologetic humble-brag: “And I just spent four Ferraris all on a brand new Bugatti and did that shit ’cause it’s somethin’ to do / Yeah, I guess that’s just who I became, dawg / Nothing was the same, dawg.”

“8PM in Mississauga” (“Club Paradise,” 2011)

For someone who’s recorded the bulk of his last five full-length projects either at his home recording studio in Los Angeles or 40’s S.O.T.A. Studios in Toronto, it’s fascinating to scan the credits of Drake’s debut Thank Me Later. With recording sessions taking place everywhere from Jamaica to Hawaii, and on buses “somewhere in New Orleans” and “somewhere in Lexington,” it’s no longer surprising why the LP feels like a rushed, pre-packaged attempt to capitalize on his sudden rise.

Knowing this, Drake relocated from Los Angeles back to his native Toronto, intent on capturing the sound of So Far Gone with Take Care. While “Dreams Money Can Buy” remains the best song left off his sophomore offering, “Club Paradise,” the final scratch which leaked two months prior to the project’s November release, is the one that would’ve fit best on Take Care.

Named after his favorite strip club in Toronto, the track is an ode to his hometown and is the moment Drake realizes that he’s no longer the homecoming hero he hoped to be. He’s melancholy about his growing fame, nervous about fucking up the double cheek kiss at New York Fashion Week, and longing for “that ignorant Young Money Miami Beach shit.”

“9PM in Miami” (“Paris Morton Music,” 2010)

In July 2010, one week after handling hook duties on Rick Ross’ “Aston Martin Music”—a record that was originally his own—Drake dropped his solo rendition, “Paris Morton Music.” Over Miami Vice-style J.U.S.T.I.C.E. League production which captured the neon lights and oceanfront highways that make night driving on Ocean Drive unforgettable, Drake laid to wax a breathless, one-and-a-half minute verse that’s arguably the best of his career. On the precipice of superstardom, just weeks removed from releasing his No. 1 debut album, Thank Me Later, Drake is as relatable, candid, and vulnerable as ever.

“Paris Morton Music” strikes the perfect balance between Confident Drake and Insecure Drake. One second he’s pondering the side effects of fame and longing for simpler times; the next he’s asking who else has fleets on their keychains and courtside seats for the Heat’s forthcoming LeBron-Wade-Bosh era.

Right after boasting about how debating Ferrari prices over lunch has him—at 23-years-old, no less—amidst a midlife crisis, he’s wrestling with insecurities stemming from his middle-class upbringing (“It take a certain type of man to teach / To be far from hood, but to understand the street”), before he goes back to rapping with a chip on his shoulder (“I never threw away that paper with my GRAMMY speech / Because I haven’t hit the pinnacles I plan to reach”).

“10PM in Chattanooga” (“30 for 30 Freestyle,” What a Time to Be Alive, 2015)

The song that best captures Drake’s mindset and mood in the ensuing aftermath of summer 2015’s ghostwriting rumors is not the track that crowned him winner of the Meek Mill beef by TKO (“Back to Back”), nor the then-biggest song of his career released in the wake of the fued (“Hotline Bling”). Instead, it came two months later via “30 for 30 Freestyle,” the closer to Drake’s joint mixtape with Future, What a Time to Be Alive, released in late September 2015.

Passing over Chattanooga on a “bumpy flight on a summer night,” Drake sounds exhausted yet re-energized. Assisted by 40’s trademark atmospheric production, he waxes poetic for three straight minutes, offering up an off-the-cuff verse that doubles as a personal therapy session. Over lush piano chords and muted synths, Drake opens the track by sarcastically congratulating Meek, Funk Master Flex, and co., for unsuccessfully destroying his career.”

Then, after touching on everything from PND’s white Porsche and his own Mercedes Pullman, to a dinner of scallops that were to die for and violence amongst Toronto’s youth, Drake throws more darts at critics by being the first to say what we all were thinking.

“11PM in Atlanta” (“Say What’s Real,” So Far Gone, 2009)

Eight songs into his breakthrough mixtape So Far Gone, Drake shows why he’s more than just an R&B rapper on “Say What’s Real.” The track serves as the moment he truly arrived, as he lets loose four minutes of hookless rapping over Kanye’s “Say You Will” beat. Taking a page out of his mentor Lil Wayne’s playbook, Drake hijacks the song and makes you forget about the original, proving that no one does emotional vulnerability better—not even Kanye.

Why do I feel so alone?” might as well be the first words he ever uttered. From there, the breathless verse sounds as if Drake’s conversing with you during after hours in an Atlanta strip club. On the cusp of superstardom at the time—months before he would blow up with his first hit, “Best I Ever Had”—he grapples with his success, spewing on about his diminishing trust of strangers.

But the highlights of the slow-burning track come later, as Drake sounds more self-aware than most rookies when he raps, “Don’t ever forget the moment you began to doubt / Transitioning from fitting in to standing out.” Then ends his first legendary confessional by plotting his next move. “I got new shit, I’m getting better still... And I think this got this making-of-a-legend feel.

If you ever forget how long Drake’s been running laps around the rap game, do yourself a favor and listen to “Say What’s Real,” then remind yourself it was recorded a decade ago, back when the biggest pop star alive was merely a 22-year-old, up-and-coming prodigy. 

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