When Hip-Hop’s Mentees Become The Mentors

Throughout hip-hop’s illustrious history, wisdom has been drip-fed from one generation to the next. Whether gleaned from the mishaps of other MCs, or through pivotal moments in which an OG has a chance encounter with a new-school rapper, the genre is only fully operational when today’s artists pay heed to what’s gone before them. After all, those who don’t know their history are, as the saying goes, condemned to repeat it. 

Jaz-O to Jay-Z 

 Jaz-O and Jay-Z, 1989 – Al Pereira/Getty Images/Michael Ochs Archives/Getty Images

Long before he was a living embodiment of the American dream, Sean Carter was just another Brooklynite with dreams of prosperity. Throughout his early career as an MC, Hov was wise enough to know that raw talent wouldn’t necessarily suffice, and so he deferred to those with greater experience. But where club promoter turned fellow Rocafella Records exec Dame Dash bolstered his promotional game and Big Daddy Kane would give him his first experience of touring, it was another MC from Marcy Projects that first took a young Jay under his wing. Signed to EMI at the time, Jaz-O was riding high in 1989 and had garnered a great deal of fanfare with his pioneering triplet flow. Cited by DJ Clark Kent as in his top 3 pens of all time, Jaz was set to be a star. But as it turned out, his own prestige would be dwarfed by the protégé that he met, after mutual friend Clyde “Nike” Harewood had maintained that Jaz was the superior rhymer of the two. 

“They was going back and forth, and they were like, ‘All right, let’s find out,’” Jaz reflected to Drink Champs. “So, he set up the meeting and that’s when me and JAY first met.  I rhymed first and then, he rhymed, and he was the first person that I ever heard rhyme [that reminded me of me]. So I was like, ‘Yeah, I gotta keep my eye on him.”

Shortly thereafter, Jaz would formally give Jay– then known as “Jazzy”– his inaugural chance to be a recording artist through a feature on “Hawaiian Sophie” from 1989’s debut album Welcome To The Jaz.

By the time that he’d drop his sophomore project the following year, the newly rechristened Jay-Z would be given two spots to show his prowess, mimicking his mentor’s flow on tracks such as “The Originators.” Once Jay established his own wave, Jaz would remain on the outskirts of the picture and famously wrote the hook for Reasonable Doubt’s “Ain’t No N***a” alongside sporadic production duties before the two would embark on a lengthy feud. 

Revisiting these early tracks, there’s no way that anyone could’ve known what sort of titan would emerge. But once Hov had cemented his place in the game and hashed out a profitable sound of his own, the Brooklyn icon and eventual president of Def Jam would look to uplift others. 

Best exemplified on 2000’s Roc La Familia: The Dynasty, Hov allocated a portion of his own platform to making careers for Roc-A-Fella artists such as fellow Marcy MC Memphis Bleek, Beanie Sigel and Freeway. In doing so, he ensured that each of these artists have Billboard-charting albums to their name. While in the case of his longtime hype man Memphis Bleek, his claim from fellow protégé Kanye West’s “Diamonds Of Sierra Leone” remix that “as long as I’m  alive, he’s a millionaire” shows the value that Jay-Z places on creating a better life for his mentees. 

Although he’s diversified into other areas in recent years and takes less of an active role in A&R, Jay has still helped a post-prison Meek Mill redefine his career, got Lil Uzi Vert out of his deal with Generation Now and, in a testament to his full circle approach, even signed Jaz-O to Roc Nation after years of beef. 

Described as playing a “big homie” role by Memphis’ Yo Gotti, Hov’s pedigree as the elder statesman is among the greatest in the game. Not least of all due to the fact that by giving him a chance to become more than just a producer, he helped spawn one of the industry’s true creative firebrands.

Jay-Z to Kanye West 

Kanye West and Jay-Z, 2015 – Larry Busacca/Getty Images

Pinpointing Jay-Z as his “big brother” and fellow producer extraordinaire No I.D as his “mentor” on 2006’s Graduation, Chi-Town’s finest was in awe when he first got to Roc-A-Fella. 

Kanye West proved himself as a bonafide hitmaker after he was given the opportunity to shine across Jay Z’s The Blueprint, and when that success bled over into his own career, he wasted little time in launching his own subsidiary. Launched in 2004, G.O.O.D Music– an acronym of Getting Out Our Dreams– quickly became a vessel for bold and uncompromising voices. From re-starting the career of Common on Be to providing the building blocks of John Legend’s superstardom with Get Lifted, Ye’spronounced ability to enter an artist’s career and enrich it meant that before long, would-be stars were flocking to Ye, trying to get his attention. 

In this respect, many of those that Kanye would mentor came to him in an unsolicited manner– and, where a more insular artist would brush them off, Kanye immediately placed them on his radar.

Among them, Kid Cudi first accosted Kanye West in a Virgin Megastore. 

“I had no pitch,” Cudi recalled, “I was just this kid that was like, ‘Can you sign me?’”

A few years after that, Big Sean cornered his “hero” at a Detroit radio station after a tip-off from a friend. 

Although artists such as Consequence and Mr. Hudson didn’t exactly set the world alight under his banner, Cudi and Big Sean’s positions as two of the industry’s leading stars are a testament to Ye’s ability to accentuate an artist’s talents in the early days and light the way to longstanding careers in the same way that Jay did for him. As a result, his mentorship is so sought after that Travis Scott ate a taco covered in sour cream– which would normally, in his words, “make me throw up”–  so as not to ruffle any feathers during their first encounter. 

Expanding on the kinship that the Houston native had developed with Kanye, Travis would later reveal that he’d actually stayed at Ye’s during the recording of the now seminal Rodeo. 

Despite the fact that he’s never actually been a G.O.O.D signee as an artist and opted to ink a publishing-only deal with Very Good Beats in 2012, it was in this period that the near-paternal dynamic between Laflame and Ye was first fleshed out. 

Lilly Lawrence/Getty Images

“He’s like my stepdad,” Travis told Billboard. “We always had that relationship where we cook up ideas. We [talk] all the time about random [stuff]: life and how we can do better as people and as rock stars. Our goal is to help people figure out who they want to be.” 

Fuelled by a shared desire to enhance their own understandings and other artists’ careers in the process, Travis’ spell of learning from Ye has paid off to the extent that, when the pair looked to sign Sheck Wes in 2018, they did so as a joint venture between G.O.O.D and Travis’ own Cactus Jack Records stable. In modern times, Travis stands tall as hip-hop’s biggest commercial draw. But if it weren’t for the early patronage and instructions from Ye, there’s a good chance that this may have never materialized.

Always receptive to drive and innovation in either music or the design world, Kanye has become the go-to sensei for hip-hop’s outsiders, and it’s safe to say that we haven’t seen the last of Yeezy in the role of advisor and facilitator of dreams. 

Birdman to Lil Wayne 

Lil Wayne and Birdman, 2020 – Gerardo Mora/Getty Images

Moving from the Southside of Chi-Town to the dirty south, another artist who has taken the entrepreneurial flair of his mentor and ran with it is none other than Cash Money’s former flagship artist and later CEO of Young Money, Lil Wayne.

Initially granted a recording contract at the tender age of 12, the adolescent who would go on to become hip-hop’s reigning king during a mid-2000’s stretch, was given his shot by Brian “Birdman” Williams. Seeing potential in him from a prodigious age, Baby stepped in as both a boss and a paternal figure to his fellow Louisianian.

“I just wanted to help him because I didn’t want him to live my life,” Birdman told Ebro Darden in 2018. “I just saw some young bro with some talent and I wanted to help him. And that’s what I did.”

Allotted a spot among the Hot Boyz, Wayne was free to hone his craft in a low-stakes situation. But when Juvenile and some of the other lynchpins of the label’s early days started jumping ship, Weezy would soon become Cash Money’s most profitable star. 

By 2005, Tunechi was awarded his own Young Money imprint, and with that, he began to create his very own hit factory. From Drake, to Nicki Minaj and Tyga, Wayne scanned the length and breadth of North America to assemble a roster who’d go on to become superstars under his umbrella.

John Shearer/BBMA2017/Getty Images

“This man believed in me after so many never called again or just didn’t see it to begin with,” Drake said of Lil Wayne in August 2020. “Most selfless artist ever, never held any of us back, always pushed us forward… 20k packed into an arena and he had a whole set of his show dedicated to introducing us FOR YEARS. All praise and credit due to the GOAT.”

Always eager to ensure that there is chemistry between himself and the artist that could translate across both collaborations and their day-to-day lives, a reflective piece from Interview Magazine saw Drizzy recall how Weezy brought him out to a Houston tour stop, based off nothing more than a few tracks that he’d heard on a burned CD. And even then, there was no formal talk of a deal. 

“The first meeting wasn’t really anything pivotal. It was cool. I think he saw that I was a good kid, or trying to be a good kid, and I was just staring at one of my idols. I stayed on the road with him for a while, about a week and a half. And I think it was the last night before I went back home, we finally got into the studio and made some music,” Drake explained.

With a whole host of his artists now flourishing entirely independently of him, and with Drake now acting as the benefactor for his own crop of up-and-comers through the OVO Sound hit factory, Weezy took the faith and trust that Birdman showed in a young NOLA native– albeit leaving some of the unscrupulous business tactics to the side–  and applied it to the careers of Nicki and Drake. In turn, creating worldwide crossover stars. For Weezy, the fact that both Aubrey Graham and Onika Maraj came up from his guidance to become household names is even more gratifying than his own storied career. 

“Probably better to know that I have a part of what’s going on with Nicki and Drake, and anyone—I’ve had Tyga, anyone,” Wayne told Sovereign Brands’ Brett Berish during a 2020 Instagram Live. “Someone that I know for a fact that we started from the bottom. I started from the ground and I helped them get to where they got. It’s like a seed you only have to water once and it never stops growing.”

Dr. Dre to Eminem

Dr. Dre, 50 Cent and Eminem, 2020 – Leon Bennett/Getty Images

By the late 1990s, Andre “Dr. Dre” Young was on precarious ground, seven years removed from The Chronic, and releasing a series of dubiously-received singles. Things started to turn around after, as the story goes, an Interscope assistant received a demo from a hungry young rapper after his set at the 1997 Rap Olympics. Said assistant would pass said demo on to Jimmy Iovine, who would, in turn, play it for Dr. Dre. Said hungry young rapper, was of course, Eminem.

“I’m looking at Dre like, dude I see you on TV all the time,” Eminem reflected on HBO’s The Defiant Ones. “You’re one of my biggest influences in life… This is the greatest producer, I’m at his fucking house recording. I just wanted to make sure that for every beat he plays me, I have a rhyme ready for it.”

Since ascending to the top of the mountain, Eminem has been eager to throw a ladder down to other aspiring MCs. Working from the Interscope-backed Shady Records, Em has had varying success as a mentor, but when he scored, he scored big. 

Five years after signing, Shady found his own ward who had similarly been deemed radioactive by much of the industry. Dropped from Columbia with just a European-only EP to show for it, Em took a young Curtis “50 Cent” Jackson under his wing and created a charismatic star that’d waste little time in putting the rap game in a chokehold.

Although 50 has since left the Interscope family, the G-Unit kingpin, much like fellow Shady protégé Obie Trice, has been candid about the fact that his fealty to Em is unwavering. Without his patronage, there is no career to speak of: “It’d be pretty tough for us to have an argument as I hold him in the kind of regard that I hold my grandparents in. He provided an opportunity to take care of myself when I couldn’t at that point. I actually couldn’t make it happen without the assistance I got from him.”

Eminem’s unending love of hip-hop meant that it wasn’t enough for him to give himself to the genre, but provide the channel for other legends to emerge.

Gucci Mane to Young Thug

Gucci Mane and Young Thug, 2016 – Prince Williams/WireImage/Getty Images

Although every artist that we’ve discussed up until this point arose from the 90s and 2000s, that doesn’t mean that modern artists aren’t striving to put others on too.  

A staple of the ATL and a trailblazer in his own idiosyncratic ways, Young Thug is an artist who has benefited from the wealth of experience that he’s been privy to. Infamously signed to 1017 by Gucci Mane without Guwop even hearing a track, Thugger would be put on the map via a 2014 collab tape Young Thugga Mane Laflare. 

“He taught me everything,” Jeffrey told The Fader in 2016. “Most definitely he taught me don’t never stop. He was rapping every day, all day and all night. He’ll be mad at me if I’d leave the ‘yo [the studio]. He’d be like, ‘Man, you dead broke and you goddamn running around and I’m up a whole lot of millions and I’m working every day. How the hell that look?’”

After acquiring Guwop’s unwavering work ethic, Thug would find another mentor in the form of Birdman. Describing him as “like a real father figure,” the pair and friend-turned-foe Rich Homie Quan seemed almost inseparable during the Rich Gang era and even now, Thug’s Young Stoner Life label and Cash Money have a working relationship. 

In the transition from artist to A&R, Thug has shown the same sort of willingness to gamble that made his mentors into industry power brokers. After spotting the raw potential in Lil Baby, Thug reportedly incentivized him to take his rap career seriously, despite not even signing him to a YSL deal.

“He literally paid me to leave the neighborhood,” Lil Baby revealed. “[He said], ‘Bruh you can rap, you got it. You could be next. You gotta leave the ’hood… I’ma pay you to come to the studio.’” 

Nonetheless, Thug also has taken many artists more directly under the YSL wing, setting up comfortable launching pads for artists like Gunna, Lil Keed, Lil Duke and others.

Through Thug’s mixture of benevolence and brotherly love to his fellow MCs, we see that the journey from mentee to mentor is alive and well. 

Prince Williams/Wireimage/Getty Images