Generations are a myth. The idea that everyone who was born around the same time has a common worldview or set of characteristics was born sometime in the 1860s, but didn’t really take off until the early 1990s. It’s a theory that was (and is) mostly loved by marketers looking for easier ways to sell stuff, but doesn’t really hold up to examination.
Despite that, generations can be a useful tool in some contexts. Nowhere, perhaps, more than in a genre of music that combines marketing and arguing like no other: rap. When looking at the landscape of rap music today, it becomes clear that the mainstream is dominated by two artists who were born within eight months of each other, who began rocketing to fame as the late aughts turned into the 2010s, and who have been at the center of the game ever since: Drake and Kendrick Lamar.
Drake and Kendrick, despite their early collaborations, could in some ways not be further apart. The hitmaker versus the critical darling; the trend-hopper versus the individualist; the constant stream of music versus the one-album-every-five-years timeline.
Yet despite these differences, they have remained the two dominant voices for over a decade. So the question: which one is the greatest rapper of their generation?
The achievements of both artists are so large in scope as to basically be unfathomable. From May 2009 to August 2017, Drake had at least one song on the Billboard Hot 100 chart every single week. That record-setting run of being on the charts for over eight years straight is unsurprisingly still unmatched. He also has the most charting songs of any artist ever, giving heft to his boast to have “more slaps than the Beatles.” His list of chart records is exhaustive enough that Billboard felt the need to lay out the ones he hasn’t yet broken.
Drake is not just a singles artist, though. His album sales are equally daunting. With the exception of 2021’s Certified Lover Boy and his 2023 collaboration with 21 Savage Her Loss, all of his albums have gone platinum or multi-platinum, as have three of his mixtapes (admittedly, with Drake the album/mixtape line is extremely slippery).
When it comes to spotting trends, Drizzy is also a master. He gave key early-career boosts to countless artists including Migos, iLoveMakonnen, The Weeknd, dvsn, and many, many more.
None of this would matter if the music wasn’t worthwhile. But it is. Drake has mastered the art of writing lyrics that concisely capture a mood. He has inspired countless listicles about which of his lines would make a perfect IG caption (Buzzfeed’s ‘76 Drake Lyrics For When You Need An Instagram Caption’ and the Knot’s ‘70 Drake Lyrics To Quote In Your Wedding, Couple & It’s All A Blur Tour Instagram Captions’ are only the tip of the iceberg). His pithy, concise, pointed couplets have come to be the language in which many fans see themselves and their lives. It’s not for nothing that he has become a master of the internet meme.
Musically, he is as experimental as any artist who’s sold 170 million albums could be. He’s not afraid of radical changes in sound (2022’s dance music left turn Honestly, Nevermind) or of putting out full-length collaborations with artists like Future and 21 Savage in lieu of solo releases. He’s as likely to put out a collection of Soundcloud loosies as he is a proper album.
And after a decade-plus of stardom, he’s arguably more popular than ever. Drake’s current It’s All a Blur Tour has been making headlines not just for the amount of bras thrown onstage, but also because of the earth shattering earnings. As of this writing, anticipation is building for his upcoming album For All the Dogs. If there’s no better way to put Drake’s popularity, consider this: he managed to generate headlines by announcing a poetry book.
Stylistically, it’s hard to argue that there has been a more influential rapper this century than Drake. He may not have invented an approach that darts back and forth between rapping and singing to the point where the line between them is nearly non-existent. But he certainly popularized it, and turned it into the lingua franca of a whole generation of rappers who need help from Auto-tune to come close to Drizzy’s sense of pitch and melody.
Kendrick Lamar’s accomplishments are equally staggering. His introduction to the mainstream came via an alignment with Dr. Dre, putting him in the elite leagues of artists like Snoop Dogg and Eminem.
If you weren’t, as the phrase goes, “outside” in 2012, it’s nearly impossible to understand the anticipation and hype that surrounded Good Kid, M.A.A.D. City. Kendrick’s major-label debut absolutely took over the rap world when it was released, and it was rightfully hailed as an “instant masterpiece.” Lamar managed to create the rare classic that was both popular and critically acclaimed. It managed to be a concept album with hit singles, a combination that had barely been seen since the days of Pink Floyd. Tracks like “Money Trees” (which eventually racked up over a billion streams on Spotify) featured catchy hooks that kept live audiences’ attention, while the album’s narrative inspired by Lamar’s own adolescence kept listeners coming back to catch the details.
Everything about the album rewarded repeat listens. What appeared to be a hook enticing listeners to booze-fueled good times on “Swimming Pools (Drank)” was, on reflection, a crushing depiction of alcoholism. The whole album was sort of like that moment writ large: multiple interpretations, multiple meanings, and another layer waiting for you as soon as you figured out the previous one.
Despite how lauded Good Kid, M.A.A.D. City was, it was Kendrick’s follow-up that would really catch the zeitgeist. Released just seven months after a teenager named Michael Brown was killed by police officer Darren Wilson in Ferguson, Missouri, To Pimp a Butterfly came out into a political climate roiling with clashes over police violence, and debate over the use of a then-still-new catchphrase, “Black Lives Matter.”
TPAB gave that movement a soundtrack. Almost immediately, protestors began chanting the hook to “Alright,” a song that had been inspired by Lamar’s visit to the location of Nelson Mandela’s prison cell. The album as a whole became, as one article put it, “a timestamp for the Black Lives Matter movement.”
The album wasn’t only important for its politics. The sound and the musical approach of the record proved as influential as its stances on contemporary issues and Black history. The album’s use of musicians like Terrace Martin, Robert Glasper, Kamasi Washington, Thundercat, and Robert “Sput” Searight, along with producer Flying Lotus, gave new prominence to an exciting, experimental hip-hop-influenced jazz scene.
Rather than resting on his laurels as the newly-anointed voice of his generation, K-Dot continued growing and changing. His third album DAMN was both more experimental and more commercial. More commercial in that it featured melodic tracks like “Loyalty.” And more experimental in its structure—speculation that it told a story backwards led the artist to issue a version of the album with the tracklist in reverse. DAMN continued Lamar’s combination of critical and commercial love: it famously both went triple platinum and won the Pulitzer Prize.
After another long break (during which his cousin Baby Keem became one of the hottest rappers in the game), Kung Fu Kenny returned with Mr. Morale & The Big Steppers. Initial reviews were more mixed than previously—for every critic hailing it as a masterpiece, there was another who, while acknowledging its brilliance, noted that the rapper seemed to be “venturing into grumpy uncle territory” with his complaints about social media and so-called cancel culture.
But a few critical complaints didn’t stop Kendrick. His Big Steppers Tour, a giant production featuring dancers, a puppet Kendrick, and narration by Helen Mirren, was the highest-grossing rap tour of all time.
All of this acclaim, for both artists, didn’t come out of nowhere. By the time Drake and Kendrick hit the Billboard charts, they had years of experience under their belts.
Lamar had put out a handful of early mixtapes starting in 2004, when he was still a teenager. Six years later, he began getting serious onstage experience by going on tour as hype man for TDE’s Jay Rock (you can read an account I wrote of that time, with memories from Tech N9ne and E-40, among others,here).
Kendrick began his career under the name K. Dot, but switched to his given name on 2009’s The Kendrick Lamar EP. His follow-up, 2010’s Overly Dedicated, got some attention, including most notably from Dr. Dre, and things were off to the races from there.
Drake began releasing songs in 2006. By that point, he was already a show biz veteran who had been appearing on the TV show Degrassi: The Next Generation since 2001.
Their early-career influences are readily apparent. The first song of Kendrick’s first mixtape uses a Vol. 3 Jay Z beat. Drake was quick to give credit to Ye, at least early on, for “a lot of inspiration.” K-Dot, as someone so closely associated with Compton, obviously took a lot as well from the gangsta rap innovations of his city—something he telegraphed by giving MC Eiht of Compton’s Most Wanted a prominent spot on Good Kid, M.A.A.D. City. While their musical evolutions have been varied, you can still see these formative influences in pretty much everything both artists do.
How do you even begin to compare Drake and Kendrick Lamar?
Both artists are so wildly successful that it’s difficult to match them against each other. They have each sold pretty much unfathomable amounts of records, though by that metric Drake is certainly the winner: over 70 million albums for Kendrick, 170 million albums (and 184 million singles) for Drizzy.
As mentioned above, Drake’s influence can be heard every time a rapper uses the word “melodic” in an interview. Kendrick, as a more sui generis artist, has proven harder to imitate. But his influence shows in other ways: in the growth of the jazz scene that To Pimp a Butterfly popularized; in the expanding influence of Baby Keem; in the college courses that teach Lamar’s music; in the ways other rappers have brought contemporary political issues into their songs.
More important than even the huge sales numbers is the creativity of both artists. It’s here that Kendrick has the biggest advantage. Drake experiments with plenty of different styles. But each Kendrick album is an entirely different experience. It has its own sound, its own concerns, its own vocabulary. It’s that approach, the idea that you never know what you’re going to get, that keeps fans coming back despite the years-long wait between projects.
Kendrick has ricocheted from coming-of-age stories to political manifestos to melodic, impressionistic storytelling to big, messy, post-therapeutic outcries. Yet all of it has remained fascinating, and distinctly him.
It’s this following-his-muse quality that has built trust between Kendrick and his audience, enough to keep them going through even the periodic difficult or off-putting moments on his latest project. And it’s this quality of doing exactly what he wants, and doing it to the highest standard, that makes him the greatest rapper of his generation, a once-in-an-era talent who we should be grateful to have working while we can experience it.
We don’t know what’s next with Kendrick, and if recent history is a guide we’ll have to wait a while to find out. He has been occupied with business ventures (and CashApp commercials) for his company pgLang, and the only songs he’s appeared on this year have been by Beyoncé and his cousin. But experience tells us that whatever he does next will be different, driven by a restless intellect searching for new ways to express himself. That alone should keep all of us listening.
