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Only Oumar Saleh knows what happened to the Russian.

Late in the first season of The Sopranos, we get introduced to rap mogul Massive Genius in “A Hit is a Hit.” Throughout the episode, Genius butts heads with Hesh Rabkin over unpaid royalties to his cousin, stemming from the Soprano family associate’s days as a label head for doo-wop and soul artists during the ‘50s and ‘60s. His part was fleeting; the last we see of him is his threat to take Rabkin to court, much to the mockery of Tony Soprano and his crew. However, Bokeem Woodbine’s portrayal of a pinstripe suit-wearing gangsta rapper represented more than a quick peek into the rap game from a mob show’s point of view. If anything, Genius was a microcosm of the series’ subversion of cliché, and inadvertently fostered a stronger connection with hip hop, just as the new millennium was approaching.

The year was 1999. The Sopranos arrived at a period where pop culture’s fascination with the cosa nostra was on the slide. While the ‘90s saw a plethora of acclaimed mob movies, by the time HBO first aired the pilot, it had become a trope as well-worn as the Western. At the same time, Mafioso rap faced a similar trajectory. After Kool G Rap pioneered it, it became a mid-90s staple (thanks to Ghost and Rae, and Nas and AZ), alongside genre classics like Casino and Carlito’s Way. Rap music was amidst the shiny suit era; Puffy and his jiggy peers owned radio and MTV. For it to regain relevance, Mafioso rap had to veer away from the glitz and glamour.

Enter The Sopranos. David Chase’s small-screen epic stands out because of its multi-layered, modern take on traditional mob stories. Set in New Jersey, it’s a Shakespearean saga of family ties, fragile egos and the dying embers of the American Dream that avoids many of the usual pitfalls that come with illustrating the criminal underworld. Instead of highlighting the corny stereotypes of late-’90s jiggy rappers, Genius is depicted as an astute intellectual with an appreciation for the Godfather trilogy. Even when rocking a gaudy leopard print-fedora, Genius is painted as a shrewd operator who more than holds his own when dealing with Hesh and the Soprano clan.

James Gandolfini’s hulking mob boss Tony Soprano is also emblematic of the series’ admirable commitment to three-dimensional characterization. As the head of the family, Soprano is an intimidating mammoth of a man who is as awe-inspiring as he is deeply flawed. He is a walking contradiction whose inner desires of becoming a better person are in perennial conflict with his basest impulses towards brutality and isolation, yet we still feel compelled to root for him despite his many terrible deeds.

Large swathes of the rap community are not immune to the veneration of Tony and The Sopranos either. Predictably, East Coast luminaries such as Nas, Cam’ron, Rakim and Redman have paid tribute, but the show’s impact isn’t limited to the Tri-State Area. Royce da 5’9’’, Gucci Mane, Tha Dogg Pound and UGK have also dropped references, and North London’s Nines has a wavy UK trap anthem named after the skipper. The irrepressible Freddie Gibbs calls himself “Freddie Soprano” in multiple tracks where he likens himself to mafiosos on the hustle. And parallels can be drawn between Soprano’s earliest sessions with Dr Jennifer Melfi and Jay-Z’s earnestly confessional 4:44. In the album, Hov references the hurt he caused his loved ones despite never really owning his actions, mirroring Tony who’s unsure of why he’s seeing a shrink and initially shows his contempt for therapeutic treatment on more than one occasion.

In the hook to “Violent,” Dave East raps, “I looked up to Tony Montana, Tony Soprano,” To compare the two icons is lazy as Soprano is the polar opposite of the cartoonishly two-dimensional Montana, but it’s important to note their source material. Both are seen as predominant influences of today’s Mafioso rap, but it’s The Sopranos’ willingness to sidestep stereotypes that has allowed it to usurp Scarface in my book. Montana’s tale has been rapped about ad nauseum, but what used to be seen as a relatable take on grinding and the come-up now smacks of nothing more than simplistic, fluorescent violence that defines Brian de Palma’s 1983 film. This shift in gears was reflective of the revival of Mafioso rap since the turn of the century, and it seems that artists from the LOX and Rick Ross to Benny the Butcher and Gibbs took heed of an important lesson: for Mafioso rap to evolve, it had to become The Sopranos.

“The theme song to The Sopranos / Plays in the key of life on my mental piano”‘The Dynasty (Intro),’ Jay-Z

Just Blaze’s triumphant production on the The Dynasty opener was symbolic of Jay-Z’s intent to take over the world with Roc-A-Fella Records at the dawn of a new millennium. The Roc were expanding beyond Hov, who had a large shadow cast over him following his stabbing of Lance “Un” Rivera and his infamous beef with Nas; other artists in La Familia such as Beanie Sigel, Memphis Bleek and Freeway began their rise to prominence. In this intro, Jay namedrops his acts with the driven optimism of a confident crew leader who knows that the world is still his but can’t seem to shake this constant urge to “get himself a gun”, triggering comparisons between his heated feud with God’s Son and the ambient violence that follows Soprano during the mob war between New Jersey and New York.

“Why am I here? That question overwhelms me / I am a gangsta, Dr. Melfi couldn’t help me”‘Hypnotic,’ Memphis Bleek feat. Beanie Sigel & Jay-Z

“Uh, I ain’t the type to take a selfie / I’m the type to need a sitdown with Dr. Melfi”‘Blue Chinese,’ Meyhem Lauren & DJ Muggs

Reading both bars back-to-back reminds me of Tony’s flippant attitude towards Dr Melfi’s sessions. He would storm out of her room in one episode exclaiming that “this is bullshit!”, but then bear his soul about the emotional cruelty his mother inflicted on him growing up in the next. Whatever Dr Melfi would later think of Tony’s intentions, their scenes together exposed us to the inner vulnerabilities of a man who eventually embraced therapy while lamenting the absence of the “strong, silent type like Gary Cooper.” Despite its roots as an ego-driven genre founded on ‘machismo’, rap has been an outlet to those contradictory feelings in recent years with the likes of Jay-Z, Mac Miller, Future and Drake earning rave reviews for tapping into themes of introspection and sensitivity. 

“Once you get into this family, there’s no getting out / This family comes before anything, it’s a thing of honor, since time immemorial”‘Burden of Proof,’ Benny the Butcher

Aside from Jay-Z, the one rapper whose oeuvre has been inspired most by The Sopranos is Benny the Butcher. The Griselda spitter’s admiration extends beyond his music and aesthetic, having formed a collective of rhymers from his hometown of Buffalo called the ‘Black Soprano Family’ of whom he calls a “gang full of Tony Sopranos who call all the shots”. While gangsters taught Benny “so much about loyalty”, it’s ironic that the show heavily depicts the breakdown of social code in many facets of modern America. The once-sacred values of honour and omerta are now gone, which irritates Soprano to no end as he was desperately trying to keep a dying code alive in the same way that Benny and many rappers place huge stock on the ‘G code’. ‘Burden of Proof’ pays homage to those tenets, as The Butcher is welcomed into the capital-F Family in a formal induction akin to time-honoured ceremonies.

“Got some models comin’ to the top floor at the Waldorf / Feel like new Sopranos ’cause we way above the law now”‘Goin’ Dummi,’ Future

From local New Jersey police to detectives doubling as private eyes, various scenes throughout The Sopranos show law enforcement being in the mob’s picket. Though not the FBI agents that frequent Satriale’s for the veal parm subs, but a cordial bonhomie is shared between them and the crew nonetheless. Tony even has a New Jersey state senator under his thumb who gets him out of skirmishes ranging from a speeding ticket from an honest cop to getting his son AJ out of custody without charge. Mafioso rap long celebrated looking down at the law, but trap poets like Future just wanted the perks that came with being that much of a boss.

“Hammers unloading ammo if his army ain’t in harmony / He kill his own famo like Tony Soprano”‘Documentary of a Gangsta,’ Rakim

In early promos and adverts, The Sopranos promised to ‘redefine family’. And while the structure and dynamics of family were already well established in plenty of Mafia works, the irony is that several key moments in the show involve Tony Soprano having to dispose of those dearest to him in both families. His best friend Sal ‘Big Pussy’ Bonpensiero was dumped in the ocean for snitching to the feds. He spared his cousin Tony Blundetto a torture session at the hands of Phil Leotardo with a single shotgun blast. Most memorably, he suffocated his heir apparent Christopher Moltisanti after a car accident which made him realise that his nephew would remain a burden to others as well as himself. Soprano’s army was never truly in harmony at any point in the series, a factor which led to their eventual demise by the series’ end.

“Some of you new rappers, I don’t understand your code / You have your man shoot you, like in that Sopranos episode”‘Carry on Tradition,’ Nas

In just one episode, The Sopranos may have done more to unravel the desperation of aspiring rappers than any WorldStarHipHop exposé could hope to achieve. During the second verse of his scathing critique of “these new rappers”, Nas shouts out the episode where a budding MC, played by Treach, was so hungry for street cred that he hired gentle giant and Soprano soldier Bobby Bacala to shoot him “in the fleshy part of the thigh”. The Hip Hop is Dead standout packed a bigger punch back in 2006 when it was first released, but it’s message to those “doing anything to get in the game” remains relevant in today’s era where clout is currency.

“Baby Tony, top of the family like Johnny Sacrimoni”‘Palmolive,’ Freddie Gibbs & Madlib feat. Pusha T & Killer Mike

“No Soprano, I run New York like Johnny Sac”‘Do Wrong,’ Cam’ron

While it’s a trite exercise to compare Tony’s Soprano and Montana, I’m almost certain that Johnny Sacrimoni was loosely inspired by Alejandro Sosa. Johnny Sac didn’t possess the omnipresent authority that the suave Sosa had over his cocaine empire, but he embodied the cultured Mafioso that was the antithesis of Soprano’s more brazen style of leadership. He was all about calm pragmatism over unnecessary conflict. And while he does crumble under the weight of the crown following Carmine Lupertazzi’s death, his run as one of the series’ more Machiavellian minds ensured that he gained a cult following among rappers who preferred his vision to Soprano’s.

“Thinkin’ I was the last one Allah would lay his blessings on / I was trying not to end up like Tony in the restaurant”‘Universal Soldier,’ Jay Electronica feat. Jay-Z

“You probably don’t even hear it when it happens, right?”Bobby Bacala, ‘Soprano Home Movies,’ Season 6, Episode 13

By the finale, aptly titled “Made in America,” the spectre of death loomed large over Tony even though he had gained the upper hand against New York. In spite of the mob war, Tony’s children were embarking on hopeful futures, while his wife Carmella was about to take another shot at a career in real estate. The family was never more content. Jay-Z, who coincidentally runs an annual festival bearing the same name as the series’ climax, reflects on his past as a dope boy before putting himself in Tony’s shoes. Over Jay Electronica’s sombre beat, he basks in the Lord’s blessings even with the gnawing fear that he can cut to black like that scene in that restaurant. Rap’s preoccupation with dying is well-documented, but it’s the concept of purgatory that arguably elicits more fear than the notion of the afterlife itself, irrespective of their actions in the mortal realm.

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