A few days ago, the XXL staff was discussing the history of New Orleans-based Cash Money Records, its unlikely ascent to cultural relevance, and its truly impressive ability to stay important and interesting over the span of twenty years in this industry. Twenty. The only boutique label that compares is Bad Boy Records, and I think we can all agree that they've had a few misfires since the Craig Mack days. The reason Cash Money is still relevant is actually pretty simple - they've stayed current. They've reinvented themselves in the face of a changing industry (in the ways that music is digested as well as purchased) and continued to re-establish themselves as a hub for great music with not only a wildly consistent output of music, but more importantly an always-evolving and diverse roster of artists.

Its unlikeliest current star (and truly, its biggest) is Drake, a.k.a. Aubrey Graham, a Canadian-born former child actor who appeared on the seminal young adult melodrama Degrassi before pursuing music full time. As the legend goes, Young Money founder and original Cash Money artist Lil Wayne was played some of Drake's music at some point in 2007, and immediately flew the young rapper down to Houston to record music and tour together. A little more than a year later, Drake released So Far Gone, an astronomically successful mixtape that sparked his career as a crossover superstar, inspired a Kanye-directed music video for its lead single, and eventually got him a Grammy nomination. All of this, from a mixtape. And in the four short years since his public debut, the guy really hasn't slowed down - he's scored sixteen platinum singles (including songs he was featured on) and two multi-platinum solo albums.

What's most incredible about his short career (again, only two albums) is that not only has he not released a bad single —not one brick in a litany of potential flops—but looking through his discography, he's never even put out a bad song. He's a good-music machine. So, to celebrate the now-26-year-old's career, and in anticipation of his upcoming Nothing Was the Same album, we put together a conclusive (in our opinions) list of Drake's 30 Best Songs to Date. Again, these are our favorites, so if you disagree, think "Started from the Bottom" should be No. 1, or "Fear" shouldn't be on the list at all, let us know in the comments section. Started… — Compiled by Dan Buyanovsky, Ralph Bristout, Eric Diep, and Emmanuel CM.

30. "Fancy" ft. T.I. and Swizz Beatz, Thank Me Later (2010)

By the time “Fancy” came around, Drake already established himself as the rapper who preferred designer suits over a pair of Timbs. We first heard Drizzy wax poetic about refined ladies on Thank Me Later. On production by Swizz Beatz and Noah “40” Shebib, Drizzy and Tip rapped about their ideal type of women who had class and a proper fashion sense. We would later get treated to the remix that included additional vocals by Mary J. Blige that stretched the longevity of the song. However, its now-famous rhetorical question ("Oh, you fancy, huh?") reassured us that it is all good to have an affinity for prestigious women. And just like Drizzy, we’re also down with girls paying for our dinners, too.—Eric Diep

29. "Houstatlantavegas," So Far Gone (2009)

Have you ever fell in love with a stripper? Many have and many soon will. Drake describes the life of a stripper/vixen in this record. The song illustrates a euphoric like state of mind where the lights are bright and the nightlife never stops. The rapper paints a picture of a woman stuck in a lifestyle she can't escape and entrapped in a cycle of repeated mistakes. The song is so smooth and mellow that it easily conceals the heart break the lyrics communicates. —Emmanuel CM

28. "Make Me Proud" ft. Nicki Minaj, Take Care (2011)

“I like a girl with a future and a past,” Drake kicks off “Make Me Proud,” his single that started an entire campaign of taking pride in a lady who stands out from the rest of the crowd. Nicki Minaj is also featured on the Take Care single, where she drops a few lines on how she’s “dominating every avenue.” Arguably, Nicki steals the show, but Drake wins for giving us a reason to say, “I’m so proud of you” many times over.—Eric Diep

27. “Closer,” Comeback Season (2007)

Before there was a bottom to start from, Drake plotted and promised his mama that he’d make it on this serene cut off 2007’s underground favorite, Comeback Season. Here he’s vulnerable as ever, but not so much that he comes off ‘emo,’ as some like to call him. Instead, the record becomes the T.O. native’s therapeutic couch, as he reminisces and reflects on his journey to fame— a journey that he best describes as going from being “Urkel for some years” to now feeling “better bein’ Jaleel.” It’s interesting though, because for someone who at the time was tied to his Degrassi-past, Drake manages to lug in a seasoned champion-like bravado on “Closer,” firing assured lines like, “First place is often the worst place/But fuck it, I love it here I call it my birthplace.” All in all, definitely a gem within Mr. Graham’s rich catalog. —Ralph Bristout

26. "Over," Thank Me Later (2010)

It's wild to look back at the video for Drake's first true single, because Drake looks a lot younger, and also because you can feel that it was the moment he became a star. But if we're being honest with ourselves, he kind of looked like a fool here—pursing his lips, over-dramatizing lines, and even fluttering his eyelashes for good measure. Still, the song is a through-and-through coming out party for Young Angel and hearing it reminds me of the time I was in a club in the Lower East Side and this came on and a crew of like twenty people got in a circle and yelled at the top of their lungs, "I'm living life right now, and this is what I'ma do 'till it's over!" "Over" was YOLO before we cared to know what YOLO was. —Dan Buyanovsky

25. "Asthma Team," Comeback Season (2007)

Comeback Season Drake wasn’t too popular, yet people still calling him Jimmy Brooks from Degrassi. Then “Replacement Girl” came out and gained him some popularity, but it was “Asthma Team” that caught hip-hop fans ears. Going in over Evidence’s “Mr. Slow Flow” beat, he’s proves he’s not just an R&B rapper, but a MC who can full-on spit.—Emmanuel CM

24. "November 18th," So Far Gone (2009)

Before "November 18th," never had a track defined a period of my life so purposefully—not to say that I was living a life parallel to Drake's, but rather that I literally didn't stop listening to this song for six months. Before A$AP was embracing H-town culture and reinterpreting the region's screwed-up sound, Drake brought it to the mainstream with this ridiculously smooth and sexual So Far Gone standout.

By juxtaposing a Biggie sample with soft crooning about "fucking you like we're in Houston," this song made you realize why Drake was bound to be a crossover success—he was a guy who could sing to the ladies but knew how to rap, making him a rap fan's singer. Or a singer's rapper. Either way, this is the kind of song that makes you want to smoke blunt after blunt on a candle-lit rooftop, exhaling slow while sipping expensive red wine. Really, it's just impressive how good Drake is at setting a mood.—Dan Buyanovsky

23. "Ignant Shit" ft. Lil Wayne So Far Gone (2009)

Drake and Lil Wayne have this sort of unique bond on tracks that bring the best out of both of them. “Ignant Shit” appeared on So Far Gone and had the pair trading off stream-of-conscious verses for five minutes. You could tell the two have some influence on each other, especially considering both ride the beat effortlessly with potent rhymes.—Eric Diep

22. "HYFR" ft. Lil Wayne Take Care (2011)

We know, the video for “HYFR” is awesome. The song again displayed Drake and Wayne’s chemistry backed by T-Minus’ rock-influenced production. Drizzy opens the track with a quick-fast verse, before passing the mic to his brother Wayne who also manages to hold his own. The acronym (hell yeah fucking right) is as celebratory as it gets. Considering “HYFR” is arguably the best banger by Drizzy and Wayne, we can’t wait to see how their next collaboration would stack up.—Eric Diep

21. “Started from the Bottom,” Nothing Was the Same (2013)

Call this Nothing Was the Same appetizer, Drizzy’s 2013 version to The Notorious B.I.G.’s rags-to-riches anthem, “Juicy.” Here, Drake adopts the age-old tale of starting from the bottom and beating all the odds set against him. It’s his own personal anthem, and that’s the overall feeling of “Started From the Bottom.” This is Drake finally basking in the glory (“I wear every single chain, even when I’m in the house”)—soaking in all the success he’s garnered since ushering in his Comeback Season in 2007. This is undoubtedly one of his many gems.—Ralph Bristout

20. "5AM in Toronto,” Nothing Was the Same (2013)

This is Drake is at his best. He’s confident, braggadocios and could give less than a two fucks about his adversaries (“Niggas make threats, can’t hear ’em over the laughter”). He’s on his King James shit, as he properly puts it in rhyme, and it’s these moments that not only wins over with his fans but the naysayers as well. With no hook, Drizzy goes in for the kill bar for bar poking fun at his opponents (“I ain't got time for a nigga who's time is comin’”), bragging about his earnings (“I made Forbes List, nigga”) and even finds time to promote those oftly popular owl sweaters (“Owl sweaters inside her luggage”). You gotta love it.—Ralph Bristout

19. "Free Spirit" ft. Rick Ross, N/A (2011)

Okay, not going to lie—after hearing this boozy, droopy would-be single off Take Care for the first time, all I wanted to do was date a girl who I'd have such an intense effect on that she'd tattoo my name on her body. It didn't happen (yet), but this song is still fucking groovy. Drake and Ross have this intangible chemistry that helps them make these songs—"Diced Pinapples," "Made Men," "Aston Martin Music"—that sound like they're just always smoking cigars and leaning back in a studio somewhere on a remote Caribbean island. "Free Spirit" strengthens their creative brotherhood and cements them as a modern day Rat Pack—or at least Dean and Frank.—Dan Buyanovsky

18. "9 AM In Dallas," Thank Me Later (2010)

What a tone Drake set when he dropped this track a few days before Thank Me Later dropped in stores. If he wrote this at 9 a.m. in Dallas just because ... this is scary.—Emmanuel CM

17. "Lust For Life"," So Far Gone (2009)

There was absolutely no better way to open the digital opus that was So Far Gone than with this. Atop a somewhat somber yet trippy backdrop, anchored by drumming 808s, we get look inside the mind of Aubrey Graham as he exhibits a dichotomy between achievement and attempt. He knows he’s on the right path especially when he rhymes lines like, “It’s funny when you’re coming in first,” but at the same time he’s self-conscious (“…but you hope that you’re last.”). All in all, it’s this combination that makes “Lust For Life” such a satisfying listen.—Ralph Bristout

16. “The Motto” ft. Lil Wayne Take Care (2011)

Drake channeled the Bay Area for this Take Care single and went on to quickly become one of 2011’s biggest records. With his YMCMB capo riding shotgun, Drizzy stamps the fact that he’s the fuckin’ man and popularizes rap’s infamous YOLO phrase in the process. The song would peak Billboard’s Hot 100 chart at No. 14 and garner a double platinum plaque.—Ralph Bristout

15. "Lord Knows" ft. Rick Ross Take Care (2011)

In this unlikely collaboration between Drake, Rick Ross, and legendary producer Just Blaze, the trio really embraces grandiosity—one thing Just has always been wont to do. This is Drake at his most braggadocios, and at his most superfluous—his verse starts out as what seems like a sixteen but goes on for a full three minutes. In the context of modern rap/pop songs, that's a ridiculous amount of time to rap for without pausing for a chorus, but he's Drake, and Drake makes and plays by his own rules.

In the epic verse, Drake spitefully shouts out the women he doesn't trust, praises Hugh Hefner and Michael Jordan as role models, and finally likens himself to Bob Marley and Jimi Hendrix—he's nothing if not wildly confident. Ross comes in for a lofty, scene-stealing sixteen—you imagine him doing the Birdman hand-rubbing thing while recording it—and drops the ultra-bossy line, "Only fat nigga in the sauna with Jews."—Dan Buyanovsky

14. "Dreams Money Can Buy" N/A (2011)

Drake had many free singles that hit the web, but none compared to the lushly-produced “Dreams Money Can Buy.” Shortly after Thank Me Later, Drizzy released this gem that had him boasting about riches, taking your girl, and making you feel really bad about it. Drake scoffing at everyone else’s (lack of) wealth is his finest hour.—Eric Diep

13. "Look What You've Done" Take Care (2011)

There's no doubt that "Marvin's Room" is Drake's masterwork, but this song is Take Care's emotional highlight, on which he conversationally raps to his mother, his uncle, and caps off the gut-wrencher with a voicemail left on his phone by his late grandma. From So Far Gone and on, he worked hard on perfecting the grounded-ness and sincerity in his lyricism, and here it's just spot-on. In keeping with the title of the album, he took extra time to work on the record—both sonically and conceptually—and with "Look What You've Done" you can really feel the time he took to properly and poignantly dissect his feelings toward his closest loved ones.—Dan Buyanovsky

12. “Uptown” ft. Lil Wayne & Bun B So Far Gone (2009)

Mr. Hardly Home But Always Reppin’, Drake comes out playing no games. Going back and forth between singing and rapping, you can see Drizzy’s versatility on this song. Reppin’ Toronto, Drizzy Drake’s bravado is in full display in his first two verses, then you have two southern kingpins end the song in Bun B and Lil Wayne—it’s nothing short of amazing.—Emmanuel CM

11. “Trust Issues" N/A (2011)

In this throwaway from the Take Care sessions, Drake reinterpolates his earwormy hook from DJ Khaled's "I'm On One" and turns it into a chopped-not-slopped ballad that only he could pull off. Looking at the timeline of his releases, this had to be a precursor to "Marvin's Room," where he got the formula down—a slow start, some confusingly dark and self-referential singing, capped off with a swaggy, Drizzy Drake-y rapped verse—before putting out the best song ever of all time. The craziest thing about this song isn't the over-the-top but somehow relatable paranoia he dives into head-first, but the fact that it was released in June—the middle of summer—but it made us feel like we were outside smoking cigarettes and hopelessly braving the unrelenting winds of a cold, cold Toronto winter.—Dan Buyanovsky

10. “Best I Ever Had" So Far Gone (2009)

Before Drake took on the role as Young Money’s leading star, he had everybody bumping his first single “Best I Ever Had.” The song—which featured the line “sweatpants, hair-tied, chillin’ with no makeup on”—had women’s appreciation written all over it. Drake had the honor of getting “Best I Ever Had” named the “Hot Rap Song” of 2009 by Billboard, and that popularity would eventually allow Drake to earn his stripes as the versatile R&B/hip-hop artist we see today. Plus, we can’t forget the video, directed by Kanye West, featuring coach Drizzy and his well-endowed team face off against a group of skilled girls. It’s one of those career-defining moments that can’t be forgotten.—Eric Diep

9. “Light Up” ft. Jay-Z Thank Me Later (2010)

Here we have the king of the rap game in Jay-Z, and its chosen child Drake team up for an absolute classic. On it, Drake describes the work he put in to get to the Hollywood limelight and become a hip-hop legend, and you have Jay describing the pitfalls to the younger rapper. A mentor to mentee conversation made into a four-minute record. It’s beautiful stuff. —Emmanuel CM

8. "Forever" ft. Eminem, Kanye West & Lil Wayne So Far Gone EP (2009)

“Last name ever, first name greatest/Like a sprain ankle, boy, I ain’t nothing to play with.” With that opening line, Drake was already cementing his place in hip-hop before he even dropped an album. On a track with superstars Kanye West, Lil Wayne and Eminem, Drizzy didn’t at all sound like a slouch. In fact, some may say he out-shined them, especially when he gets in the zone during his one-word rhymes.—Eric Diep

7. "The Calm" So Far Gone (2009)

Every once in a while, we get to see this side of Drake. No singing, no hooks, no catchy lyrics—just raw emotion; truth put on paper and turned into a record. Here we have Drizzy in a zone completely opening up about his family, the pressure of success, his love life, and his friends. The quote from 40’s mother, "Don't ask permission, just ask forgiveness" is perfectly fitting.—Emmanuel CM

6. "The Resistance" Thank Me Later (2010)

Drake really opens up about how fame has affected his relationships with his past friends and significant others. The young MC describes the dreaded statement most celebrities encounter, “you’ve changed.” The rapper even questions whether he took the right path, describing the disconnect he’s had in his relationships. It’s a powerful song with a powerful message—what’s the cost of living your dream?—Emmanuel CM

5. "The Ride" ft. The Weeknd Take Care (2011)

Give your favorite rapper a hundred tries and he wouldn't come up with a better album closer than Take Care's "The Ride," Drake's best collaboration with sort-of protege The Weeknd. It plays like the end of a crime saga where the good guy wins, but in a way that he's not too happy about. This song is all mood, and like most of The Weeknd's music it lives in a world of too much sex and too many drugs, but Drake grounds the track with a genuine tone and true realizations about sex, money, and integrity.

Drake's become famous (and is often ridiculed) for lamenting his fame—as if it's actually something to feel bad about—but this is his most potent opus, making you realize that the only thing harder than getting to the top is trying to stay there, all while keeping your head on straight. Still, despite the reflections it ends up a relatively positive affair as he looks ahead with the line, "My sophomore, I was all for it, they all saw it/My junior and senior will only get meaner/Take care…"—Dan Buyanovsky

4. "Fear" So Far Gone EP (2009)

On “Fear,” Drake gets a chance to vent about struggles and misconceptions that come with being a rapper very much involved in the industry. He's conveying that its not just glitz and glamor, but rather cruel politics and shady characters. He gets into painful details about his emotional stress from fame and money.—Emmanuel CM

3. "Successful" ft. Trey Songz & Lil Wayne So Far Gone (2009)

One of the lines that paints a vivid picture on this So Far Gone gem is when Drake rhymes “I know that it’s coming, I just hope that I’m alive for it.” This account along with the song’s most endearing moment, where he touches on his family turmoil (“And my mother tried to runaway from home/But I left something in the car and so I caught her in the driveway…”), are what makes “Successful” such a yearning yet brilliant song. This was the Toronto-bred MC’s proper introduction into the game. The rest as they say, was history.—Ralph Bristout

2. "Say What's Real" So Far Gone (2009)

Some say that 808's and Heartbreak helped birth Drake's post-Comeback Season style, and if you listen close to some of the slower tunes on So Far Gone it's kind of hard to argue, but on "Say What's Real," Drizzy raps over Kanye's "Say You Will" and more than makes it his own. On it, he started to fully identify with his earnest emotional side with one hand to the sky and the other hand firmly and confidently grasping his nuts as if asking listeners, "yeah I'm emotional, so what?" He even throws in a few barbed disses here, "Lost some of my hottest verses down in Cabo/So if you find a Blackberry with a side scroll, sell that motherfucker to any rapper that I know/'Cause they need it much more than I ever will/I got new shit, I'm getting better still." Truuuuu.—Dan Buyanovsky

1. "Marvin's Room" N/A (2011)

When Drake first teased his sophomore album, Take Care, with "Dreams Money Can Buy," the ravenous music world got a taste of where Drizzy was headed with his new project—a softer, more thoughtful, and less-aggressive-but-still-confident direction. It wasn't until the release of "Marvin's Room," though, that we flipped our collective shit for what Drake was about to do to our lovelorn brains. The song starts out with a desperate voicemail left by who you assume is his ex-girlfriend, then fades into some pensive singing about his current role in said ex's life, and ends with a sung/rapped verse that really just sums up being a male in the 21st century.

When I first heard him rap, "I think I'm addicted to naked pictures and sittin', talking about bitches that we almost had," I felt like he'd personally divulged my collegiate experience in one line. Then when I heard him sing, "I had sex four times this week, I'll explain," I was quickly prompted to update my Facebook status to "I had sex no times this week, I'll explain." My honesty unfortunately going in the wrong direction, but the point was that Drake was getting us to divulge things about ourselves because he was laying it all on the table.

If nothing else, this song explains a lot about Drake and the way he's utterly consumed by an assured self-awareness, yet still plagued by a sinister self-pity. Sure, his worldview is fucked, but who among us can't relate to looking at pictures of an ex and wanting to drunkenly tell her, "I'm just saying, you could do better"?—Dan Buyanovsky