Kanye West is undoubtedly one of the most critically acclaimed musicians of the 21st century. But it's not only his musical career that's been entertaining to follow. From famously interrupting and ruining Taylor Swift’s 2009 MTV Video Music Awards acceptance speech because he believed Beyonce had been snubbed, to claiming that his utterly strange support of Donald Trump was “God’s practical joke on all liberals," the Chicagoan has cultivated a public persona of being brash, arrogant and bizarre. But let's face it, the man's a born entertainer and this audacity absolutely spills into his music. Since 2004, when he strode into the rap scene with his first project, College Dropout, it's been mostly back-to-back hits. To avoid a sophomore slump, though, Kanye knew he had to build off the foundation he laid on his debut. Which is exactly what he did in 2005 with his exquisite follow up album, Late Registration.

Call him what you will -- Hov, Jigga, or simply Jay-Z -- we’re talking about one of the most influential voices in the world today. Jay-Z's gimlet-eyed focus has turned him into the quintessential black capitalist, an entertainment business mogul with a career pathway strewn with Grammy awards, advertising sponsorships, record labels, and philanthropic endeavors. In 2019, he was named by Forbes magazine as the first hip-hop artist billionaire, thanks to investments in clothing, champagne, cognac, the ride-hailing service Uber and his Roc Nation entertainment company. But none of this would have been possible without his music. Born Shawn Carter, he grew up in Brooklyn's tough Marcy Houses projects and broke onto the scene with his 1996 debut album, Reasonable Doubt. His profound talent as a lyrical marksman was immediately apparent as was his commitment to tell the stories of black men trapped, and too often killed, by the cruel system in which he was raised. But after national success with his debut, could he prove himself on the worldwide stage with his 1997 sophomore album, In My Lifetime, Vol. 1.?

Kanye West Jay-Z Album

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LYRICISM

Jay-Z's sophomore project In My Lifetime, Vol. 1 helped solidify his reputation as a true wordsmith. Showcasing his uncanny storytelling abilities he effortlessly raps about his rapid upward trajectory, the conflicting emotions of sudden stardom, and becoming the hottest new artist in Brooklyn. On the first track, “Intro/A Million and One Questions/ Rhyme No More,” he dives right into calling out the doubters and detractors:

"A lot of speculation
On the monies I’ve made, honies I’ve slayed
How is he for real? Is that N***a really paid?
Hustlers I’ve met, dealt with direct
Is it true he stayed in beef and slept with a TEC?
What’s the position you hold?
Can you really match a triple platinum artist buck by buck
But only a single goin’ gold.”

Never mind that Reasonable Doubt, Jay-Z’s debut album, only achieved modest success on the charts and sold less than 500,000 copies in the first year -- it doesn’t stop him from bragging openly about his newfound riches: “Can you really match a triple platinum artist buck by buck/ but only a single goin’ gold.” He even audaciously compares himself to the then King of New York, Notorious B.I.G., who had only recently been murdered. Reminding everyone of his “triple platinum artist” status, Jay-Z wastes no time swooping in to claim the title for himself.

While his debut was all about exposing his mafioso style and bad boy mentality, by contrast In My Lifetime is an up-close-and-deeply personal story that showcases Jay’s talent for mining the emotional landscape. In “You Must Love Me” he opens with a verse to his addict mother, who was struggling with her own demons when her son began selling drugs: “All you did was motivate me: 'Don’t let ’em hold you back!’/What’d I do?/Turned around, and I sold you crack.” It’s a harrowing account of a miserable childhood of violence, drugs, and a sadly marginalized life. Through it, he continues to rap, “You must love me,” which rings out like a sombre and beautiful echo. On another track, “Imaginary Player,” he appears eager to show his young followers that business acumen and rap can coexist:

“You got show dough, little to no dough
Sell a bunch of records and you still owe dough
I got 900 and 96 plus 4 mo’ dough”

Jay’s distrust of record companies was well documented even early on, leading him to form his own lucrative label with Dame Dash in Roc-A-Fella Records. In the clever bar above, he warns artists who are languishing in dead-end record labels, making money only from performances and not from album sales. In many ways, In My Lifetime served as one of the first manifestos on how to break free of the shackles of poverty and achieve success. And when it’s narrated by one of the greatest storytellers in rap history, you listen.

Regarded as one of the finest hip-hop albums of the century, Kanye’s sophomore work Late Registration also touches on thorny subjects such as poverty, drug trafficking, racism, the toxic college fraternity culture and the blood-diamond trade. By doing so, Kanye proved, especially in 2005, that he was one of the only mainstream rappers willing to tackle political issues. In “Diamonds,” he raps about the links between the jewellery trade and Sierra Leone's civil war. In “Crack Music,” he exposes the oppression of black militancy by drug use, while in “Roses,” he takes on America’s healthcare crisis. Not a natural storyteller, Kanye’s lyrics show flashes of brilliance occasionally. But no one can ever accuse him of not using his platform to shine a spotlight on controversial topics -- which is more than you can say about his peers.

Late Registration is peppered with skits and acapella monologues to relay various tales, including one about Kanye joining a black fraternity, where a proletarian ethos rules: no need for fancy cars or trophy girlfriends. However  Kanye is expelled from the fraternity after getting caught breaking the rules: making beats for money, taking showers, and buying new clothes. It’s Kayne’s attempt to debunk the myth that the American dream is attained only through materialism. “Gold Digger” is unquestionably the best-known song on the album. Featuring the sensational voice of Jamie Foxx, Kanye delves into a narrative about the dire life of an African American man being financially manipulated by his wife, a.k.a. the gold digger.

“I know there’s dudes ballin’, and yeah, that’s nice
And they gonna keep callin’ and tryin’, but you stay right, girl
And when you get on, he’ll leave yo’ ass for a while girl”

Then comes a superb plot-twist: after being faithful and sticking with his wife through all their trials and tribulations, the husband betrays her with a white woman. The gold digger needs a rich man, the rich man needs a trophy wife. It’s life in hip-hop ville, according to Kanye. “Addiction” is an underrated gem on the album, and in it, Kanye explores the existential dilemma of finding satisfaction through life’s vices:

“What’s your addiction? Is it money? Is it girls? Is it weed?
I’ve been afflicted by not one, not two, but all three”

He continues:

“Why everything that’s supposed to be bad make me feel so good?
Everything they told me not to is exactly what I would
Man, I tried to stop man, I tried the best I could
But you make me smile”

Kanye’s music is his conduit to relay stories about his life, his addictions and his obsessions. And Late Registration is full of relatable stories. He may well be a better producer than a rapper, never having delivered anything as lyrically intricate or smooth as our man Jay. But Ye, even back in the 2000s, was savvy enough -- and you can't deny his passion and determination -- to know that storytelling brings people together.

Kanye West Jay-Z Albums

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PRODUCTION

Kanye’s production skills are second to none. Late Registration is proof of his talent. The early 2000s saw work from many memorable producers but Kanye was one of the first to use samples and orchestral melodies behind his drums to provide upbeat and soulful tempos. Aside from Dr. Dre and Scott Storch, he was one of the earliest to introduce the piano to the genre, which has since become one of the most used instruments in hip-hop. It's often said that Kanye is one of the best producer-songwriters in music history and this album was probably where that legacy first took root.

In My Lifetime showcases textbook, New York-style beats from the late 90s. Puff Daddy’s production team, The Hitmen, handled this album and included beat masters such as DJ Premier, Ski, Buckwild and Prestige. With the expertise of this top-tier production ensemble, the album possessed a vastly more polished sound than its predecessor. It even featured a series of cleverly placed samples that included Biggie Smalls on “Face Off” and Benjamin Lattimore on the intro track. In retrospect, it’s clear that this was the pivotal moment when Jay-Z began honing his musical techniques and decided to transition from using standard drum beats to more sophisticated ones.

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IMPACT

In My Lifetime Vol. 1 and Late Registration are undoubtedly two of the most prominent hip-hop albums in the past thirty years. For Jay-Z, it was his first opportunity to start a global dialogue about his impoverished beginnings, paired nicely with some bragging about his jiggy and newfound lavish lifestyle. But at its core, it was an album that spoke to the streets and all of the young people living there who endure so much. Go ahead, dream, Jay-Z tells them, because you too can straddle both extremes.

For Kanye West, Late Registration was proof of his brilliance and his role on this earth: to transform the production-scape of rap albums forevermore. People also learned that he’s an artist willing to start necessary dialogues by going to places many rappers are too afraid to deal with. The world got their first taste of the full Kanye West package with Late Registration, hailed an “undeniable triumph” by Rolling Stone magazine and adored by millions. Let us know which album you think is best.