Every superhero needs a sidekick. Batman has Robin. Robin Hood has Will Scarlet. Matt Damon in Good Will Hunting has Ben Affleck. Mr. Burns has Smithers. The list goes on. This trope lends itself nicely to hip-hop, a genre where self-mythologizing counts almost as much as mic skills, and most rappers attempting to cement themselves as superstars end up trying to prove their influence and impact by introducing the world to their protege, usually a lesser talented friend from back in the day, usually to disastrous (or at least very goofy) results.
When Busta Rhymes — once a Tribe Called Quest hanger-on himself — became a pop star, he brought along a dude named Spliff Star. When Cam’Ron and the Diplomats crew were in striking distance of taking over hip-hop, they did so with Freekey Zekey, a terrible rapper but amazing personality who I once saw walk on stage wearing a bathrobe while kissing his muscles. There are more — Murphy Lee (sidekick to Nelly), Trife da God (sidekick to Ghostface Killah), Chevy Woods (sidekick to Wiz Khalifa) — but the point is that the road to hell is paved with good intentions, and good intentions cause rappers to hire their friends to sneak their weed through airport security in exchange for occasionally getting a verse on the single.
Of all the sidekicks, the weed carriers, and otherwise unfairly denigrated figures in hip-hop, Memphis Bleek stands head and shoulders above the rest. For over two decades, he has played second fiddle to Jay Z, catching flack from rap fans, his labelmates, and even Jay himself, and keeping his head held high all the way through it. He is the most lovable loser in hip-hop, and his reputation as Jay Z’s hapless understudy obscures his own talents.
According to hip-hop lore, Memphis Bleek was some kid who grew up in the same Brooklyn housing project as Jay Z, who Jay mysteriously plucked from obscurity as he was recording his 1996 debut album Reasonable Doubt. The reality is a bit less random. In an interview with the vlogger DJ Vlad, Bleek explained that in addition to hailing from the same neighborhood, his mother was best friends with Jay’s sister, positioning Jay Z — who was older, and unlike Bleek, no longer selling drugs to get by — as a default “older brother” figure in his life, someone who’d visit him and implore him to get out of the streets. When Bleek was in high school — in the interview, he estimates that he was around 14 or 15 — he showed Jay that he could rap by freestyling for him, earning his respect in the process.
Shortly thereafter, Jay Z took him to a studio where he was recording Reasonable Doubt, handed him a piece of paper with the lyrics to a track called “Coming of Age” written down, and, per Bleek, told him, “As fast as you can remember this piece of paper [is] as fast as you’ll be on.” The track took the form of a dialogue between a street-hustler statesman, played by Jay, and an energetic young upstart, played by Bleek, in which Jay condescendingly teaches Bleek how to sell drugs. In addition to being one of the best tracks in Jay Z’s catalogue, it inadvertently ended up setting the tone of Bleek’s entire career.
Since that moment, Jay Z has taken Bleek under his wing much in the same way that Donald Trump takes people under his wing, subjecting him to a string of indignities that can only be communicated in the form of a bulleted list. They include:
Being forced to record a sequel to “Coming of Age” in which Jay Z reads Memphis Bleek’s mind and talks about how he has the power to murder Bleek at any moment.
Having to title his debut album Coming of Age, further connecting him to a series of songs in which Jay Z teaches him how to sell drugs, then develops psychic powers, and announces to the listener that the non-psychic Bleek is disposable.
Failing to record any hit songs because he’s clearly being forced to rap over beats that Jay Z didn’t want on his own albums.
Getting made fun of by Jay Z in the hip-hop tour documentary Backstage for not being able to handle the pressures of fame, while wearing a jacket with his own name on it.
Jay Z showing up on “Change Up,” off Memphis Bleek’s second album M.A.D.E., to declare that the beat Memphis Bleek just rapped on is “bullshit.”
Showing up in Jay Z’s documentary about his fake retirement, Fade to Black, to take Outback Steakhouse orders for everybody in the studio.
Ceding an entire song of his 534 album, “Dear Summer,” to Jay Z, and having it end up being his most-streamed song on Spotify.
Eventually declaring bankruptcy and disclosing that he only had $100 to his name.
It should be said that Memphis Bleek recorded some great music when he wasn’t busy taking Jay Z’s guff. His albums, especially the aforementioned 534, are full of hidden gems, and it’s easy to imagine a world in which his style — hard-edged, gruff, passionate, and direct — could have made him an underground hip-hop hero in the vein of his frequent collaborators, Brownsville yell-rappers M.O.P. Instead, he was trapped in the liminal space between indie and mainstream, taking lumps from his mentor simply because he was good at being Memphis Bleek while sucking at being Jay Z 2.0.
In the past couple of years Memphis Bleek has stepped back from rapping, focusing instead on promoting other artists while working more or less full-time for Jay Z’s cognac brand D’ussé. It’s not exactly a glamorous life, but it’s one he seems happy with: he’s now married and has a kid, and when he does make public appearances it’s usually to set the record straight about New York hip-hop history, chronicling the early exploits of his former label Roc-A-Fella, or simply cutting up with old friends.
In my mind, the totality of Memphis Bleek can be summed up in a single YouTube video. Specifically, this one. It’s from a couple years ago and finds Bleek and his own protege, the dextrous rapper Manolo Rose, in the studio with the legendary New York hip-hop radio DJ Funkmaster Flex, freestyling. The focus is on Rose, the new talent who Bleek is introducing to the world, but after he finishes rapping, Bleek takes a turn at the mic.
He starts out rusty, not as agile or aggressive as he once was, but he makes it through the track without embarrassing himself. It’s by no means a great freestyle, but it’s not terrible either, it mainly just is. But as the beat ends, Bleek demands that Flex run the beat back so he can rap some more. In music and in life, Memphis Bleek keeps going.