TOP 10 Biggest Bosses In Rap

We take a look at the different reasons all these artists are bosses in their own right.

The current industry model, or lack there of, that we see today has created an immense shift in the climate of Rap music and Hip Hop as the culture which has resulted in a myriad of Cinderella-rivaling success stories and a new hierarchy of MCs. The best example one could use to describe the momentous shift the Rap game is experiencing would be the sort of position-less basketball/super-team trends we’ve seen developing in the NBA over the past decade. Without getting too in-depth, the main takeaway here really is this; just as a power forward needs to be able to have the mobility of a shooting guard in the NBA, a producer or rapper now has the ability to also play the role of label executive and beyond. To go even further, just as we saw an exciting off-season filled with mind-boggling trades, the industry is experiencing players move around as well.

his wave of change has pushed the industry into a new direction, where artists value and promote independence, more than large corporate label representation, and with the influence of social media and streaming platforms they’ve been able to increase their reach tenfold, too, skipping any barriers from connecting directly with a fanbase, that might have been there a decade ago. The environment in the rap game now is much more favorable for artists and producers to become bosses in their own right, and carve out their lane in the industry. The youth are learning how to make their mark too, although they’re not quite boss-level status like the artists on this list — for example, someone like Rich Chigga, who wasn’t even in the United States when his single “Dat Stick” went viral in 2016, and now, a year later, is in the middle of a massive tour. And to think he hasn’t even released a single project. Or what about the meteoric rise of Cardi B, from literally dancing as a stripper to making money moves as one of the hottest female MCs with a no. 1 single and dummy clout to flex.

With all these new kids on the block painstakingly making their claim to the game, one has to ask, who are the real deal, biggest bosses of the Rap game in 2017? We’re breaking it down for you. From every aspect, including net worth, entrepreneurial success to multi-hyphenate versatility as an artist, here are the 10 biggest bosses in the game.

Please note: we looked to artists to fill this list, rather than straight-forward management or label heads. Also, these are presented in no particular order.


Sean John “Diddy” Combs is the epitome of what a boss is, staggeringly so, he has been for more that twenty years now. Diddy’s resume is so impressive and decorated that it’s actually hard to really do him justice without losing breath. He’s received a ton of accolades throughout his career including three Grammy Awards and also wears the permanent crown for having the first rap song to debut at No. 1 on the Billboard Hot 100 chart.

There’s more, obviously. He’s appeared and/or starred in over eleven films and released six solo studio albums, in addition to the twelve RIAA Gold and Platinum certifications he has received as both an artist and a producer. But what is probably Diddy’s most boss-like quality is his ability to reinvent his brand to remain a constantly relevant force within the culture where others have faded away, and successfully navigate entrepreneurial ventures outside of the music industry. According to a report from, in 2007 when Diddy was tapped by British multinational Alcoholic beverage-maker Diageo to handle the marketing and promotion of Ciroc Vodka, the equal-share-venture was estimated to be worth $100 million, with profits split half-and-half between Diageo and Diddy. In the past couple of years, it’s been estimated that Ciroc sells around two million cases per year (upwards from a “measly” 40,000 cases in 2009), so we can only imagine what that check looks like. Beyond just Ciroc, Diddy’s beverage game includes DeLeon tequila checks, and Aquahydrate checks. Furthermore, he owns a majority of the fast-growing Revolt TV company that is carried by Comcast, AT&T U-Verse and Direct TV.

Keep in mind, that Diddy has done all of this while still maintaining his record label Bad Boy since 1993, which was once estimated to value $100 million, in addition to maintaining the Sean John brand since 1998 (still! The velour sweatsuits are making a comeback too, which could very well mark a resurgence of his fashion brand). All in all, in his two-decade spanning career Diddy has managed to diversify his income portfolio tenfold as well as elevate and change the lives of numerous artists he has worked with, all while making millions. $820 million to be exact, according to Forbe’s estimation. As for his prowess in business, Diddy gave his own perspective on it back in 2014: “I am that blend of art and commerce. So I pay attention to the business needs, the sensitivities of my partners and how to manage budgets, how to market a great product. But at the same time, I know how to use marketing and entertainment. I enjoy that creative process because it lets me go into that artistic side, not the celebrity side, that’s in me.”


In short, Rihanna does numbers. She was very recently awarded the crown as No. 1 artist in the 25-year history of Billboard’s Pop Song Charts — despite only entering the charts in question mid-way through their creation. She has eleven No. 1s on the Hot 100 chart, a record she shares only with Katy Perry, and thirty-one top 10 appearances. She has been awarded Gold and Platinum certifications from the RIAA sixty-seven times, with her latest body of work, ANTI, going double platinum back in April, while her smash single from the project “Work” has been certified six times platinum in June. This barely scratches the surface of her career, which has garnered eight Grammy Awards, twelve Billboard Music Awards, twelve American Music Awards and eight People’s Choice Awards.

Beyond simple doing impressive numbers with her music and reach as mega-pop-star, she’s seen immense success in the beauty and fashion industries respectively, all the while her extremely loyal Rihanna Navy championing behind her. In the span of about three years, Rihanna managed to rake in millions from the release four fragrances, including the 2011 “Reb’l Fleur,” which was estimated to gross $80 million according in its first year on shelves. As for her stake in fashion; well, it goes without saying she’s influencer when it comes to trends and styles in general, and thus she’s been tapped by major fashion houses including Armani, River Island and Manolo Blahnik. She made history in 2014 when she was announced as the new face of Dior, making her the first Black woman to be the face of the brand. She was announced as the Creative Director of sportswear brand Puma in 2014, signing on for a multi-year partnership, that ultimately has let Puma’s light shine its brightest in recent memory, bringing back their ‘cool’ factor. She has her own line with the brand too, FENTY, which itself has been wildly successful, ranging the gamut from sneakers to clothing.

She established a beauty and styling agency in 2015, dubbed Fr8me, based in LA. The agency specializes in assisting artists with booking commercials, editorial shoots, ad campaigns and red-carpet appearances. In 2017 she took beauty a step further, establishing her own cosmetics company, Fenty Beauty, under LVMH’s Kendo brand, with the brand doling out a reported $10 million in order to partner with RiRi.

Not to mention that through it all, Rihanna has maintained a stronghold of her musical career and subsequently has her own label, Westbury Road Entertainment, and of course, she has a stake in Jay-Z-led Tidal. Her networth is estimated at a cool $230 million in 2017.

Jay Z

Jay-Z’s stakes have changed over the course of years in the industry, but if anything, they all show his business acumen — from Def Jam, Roc-A-Fella Records, to Roc Nation, TIDAL and the Brooklyn Nets. He’s paired a stealthy businessman approach with an El Jefe reputation within the music industry itself, going so far as to remind of this fact, when he dropped 4:44 on our headtops.

The album went platinum in six days due to an exclusive distribution partnership with Sprint, a boss ass W in its own right, but 4:44 isn’t nearly as much about the numbers as it is about the theory and ideology within the release. Between the releases of Jay Z’s Blueprint 3 album and 4:44 there is an eight year gap, with Magna Carta Holy Grail smack dab in the middle. That’s hard to believe, given the fact that we are talking about the same guy that has thirteen solo studio albums, and more than 55 million records sold worldwide.

With the somewhat surprise release 4:44 in June, Hov did two things; first, he brought the crown back to his head as one the most, if not the most, elite lyricists. And second, he sonned the industry with insight and advice for the youth, while also letting the industry in on very personal thoughts and experiences (a showcasing of honesty unlike anything he’d done previously). The lead single from the album, “The Story Of OJ,” is the best example of how easily Jay-Z can push buttons and set the entire game on fire. He effortlessly touches on some of the most tumultuous topics in current events, targeting social justice issues and providing valuable rhetoric aimed one foul swoop. He attacks colorism and racism with his explicit yet effective hook. He speaks directly the underrepresented and impoverish with lines like, “I told him, “Please don’t die over the neighborhood / That your mama rentin’ / Take your drug money and buy the neighborhood / That’s how you rinse it”

Beyond simply bossing up with the release of 4:44 this year, Hov leads by example. Despite the fact that we do tend to reeceive a lot of negative reports on TIDAL’s efforts, since Hov bought the company, and Sprint invested $200 million in January, the company’s estimated worth has increased ten times what Jay paid, to $600 million. He’s also maintained steady growth for his companies Roc Nation and Armand de Brignac champagne (which he acquired in 2014).

Forbes estimates his net worth to be $810 million in 2017.


As if 431 consecutive weeks on the Billboard Hot 100 chart wasn’t enough of an indicator that Drake is a boss, these days you can catch him reporting live from court side of the Raptors game with a Pinot Grigio in hand, chopping it up with Matt Devlin and Leo Rautins. I mean the guys is literally the definition of “Best Life.”

Although we constantly see him posted up in the lap of luxury, living between beautiful homes in Toronto and California, he’s still of a business mindset. OVO is quickly turning into some 2009 Young Money conglomerate-type shit, as Drake and all of his affiliates are dominating their respective arenas right now, even if their numbers aren’t Drake-level, the clout and respect they’ve all earned is in place. That’s the true essence of Drake’s power as a boss, his ability to craft an impeccable team. That team will continue to dominate this year, since each member is expected to release a new commercial album, with dvsn already knocking theirs out.

OVO won’t be slowing down anytime soon, considering they announced a hefty expansion of their partnership with Warner Bros. Records back in May and are virtually immersed into every aspect of the culture. OVO Sound Radio is basically the most coveted on Apple Music, when it comes to exclusive releases and mixes. Drake’s partnership with Apple, which extends beyond just OVO Sound Radio, is said to be worth $19 million. In 2013, he inked a deal with the Jordan brand (reportedly worth $10 million), and now his sneakers are being re-sold for insane prices.

Drake has worldwide fame, and it shows, as his Summer Sixteen tour grossed $84.3 million. He’s in tune with innovators of every genre, and ensures he’s on them before it’s too trendy. He can make an Afro-Pop smash with international phenom Wizkid and then turn around and recruit Grime legends like Gigs and Stormzy for one of the biggest albums playlists of 2017, More Life. Added hats off to the guy for co-signing countless sensational artists like Sampha and Jorja Smith, while constantly looking out for his home city of Toronto too.

Forbes estimates his 2017 networth at $90 million, which may not yet be the heights of Diddy and Hov, but he’s well on his way, at half their age too.

Rick Ross

Young Renzel is hands down the Don of the 305. When you think of Miami, you probably think of legend Trick Daddy and of course, none other than Rick Ross. Born in 1976 in Clarksdale, Mississippi (but raised in Carol City), Leonard Roberts II began his rap career under the stage name Teflon Da Don although that was changed to the current moniker by the 2000s, between deals at Suave House Records and Slip-n-Slide records. By the mid 2000s he’s was on his way towards an epic run as one of the hottest MCs to rise out of Florida in the last 20 years. Although he may not actually have kingpin roots like the man he borrows his rap name from, he’s definitely hustled to get to his current position.

Fast forward to 2006, and the releases of Rick Ross’ debut album Port Of Miami yielded a Billboard 200 No. 1. His 2008 sophomore follow-up Trilla debuted at the top of the Billboard 200, quickly paving the way for his third album Deeper Than Rap and more importantly, one of his biggest business ventures, Maybach Music Group aka MMG, in 2009. By 2011, Ross had released five studio albums and several well-received mixtapes, thus with a solid foundation underneath him as an artist, he sought out to expand his MMG imprint. He signed two of the biggest artists of our generation, Meek Mill and Wale, both still flagship artists for the label. Today, he continues to expand the roster, recently announcing signings of Bruno Mali (a Miami native himself) and Jeff Chery — both are up and comers, and prove Ross’ loyalty to Florida and the hip-hop game in general.

And in addition to MMG, Rick Ross is the proud owner of several Wingstops — it’s unclear the total number, but it lies somewhere between 10 and 25 locations. These spots are estimated by Forbes to bring him in $7 million in revenue per year. In other words, Rick Ross’ career sums up the foundation of what the proverbial “American Dream” is. He essentially started out from nothing, hell, he was even a Corrections Officer for a few years, and was rumored to have been homeless at one point too, but he still managed to become one of the biggest recording artists and build a record label that looks out for its own beyond just churning out music. His latest move has been purchasing a Checkers location that’s near and dear to his heart, continuing to “Buy Back the Block.” It is these sorts of moves that earn Ross a spot on this list, despite his networth not being quite up to par with the likes of Diddy– Rozay’s is reported to be around $30 million. Although, like Diddy, Ross too has a stake in the beverage game, with constant promotion of his Belaire Rose brand, which Ross got on board with in 2013.

So next time you bump some Meek or pick up a hot 10 Pc. Lemon Pepper wings with fries from Wingstop, just remember that it’s all powered by Young Renzel aka Rick Ross aka the boss.

DJ Khaled

So here’s a hypothetical for you. Say it’s your son’s first birthday and you decide to throw him a party, what are you going to do? Does it involve gifting him a $100,000 Rolex watch, or throwing an extravagant blowout at Liv Lounge complete with dancers and celebrities? If you are DJ Khaled, then the answer appears to be a yes. After all, your son did executive produce your platinum-selling album, Grateful. In all honesty, DJ Khaled’s entire existence is boss AF.

Love him or hate him, there is no denying his impact, work ethic, and determination, all proven boss-factors. From his larger than life Snapchat persona and catchphrases, to his mega singles (six of which received platinum certifications this year), Khaled has worked incredibly hard for the success he receives today, and he’s got the receipts too, from his very early beginnings as a record store employee, to hosting a radio show in Miami in the late ’90s.

He really got his start as a a radio personality for Urban radio station WEDR “99 Jamz,” and managed to literally work his way up the ranks and seize every single opportunity possible in order to level up. Whether it was DJing for the legendary Bronx Rap group Terror Squad or producing for Fabolous and Fat Joe, Khaled was always “up to something” as he frequently denotes, still to this day. In 2006, DJ Khaled released his debut album Listenn…. the Album, an effort the streets welcomed, peaking at No. 12 on the Billboard 200. For the next ten plus years, Khaled would become known as the hitmaker curator, and release a slew of anthems including “All I Do Is Win” and “I’m On One.” While most know DJ Khaled for his work in the booth and pulling those studio strings, many overlook the fact that he is just as much an entrepreneur and an executive.

He is, of course, the CEO of We The Best Music Group, while he also maintained a stint as the President of Def Jam South from 2009 to 2012. He’s continued to strengthen his We The Best brand, not only making it a catchphrase in its own right, but getting a radio show for it on Beats 1 and a deal with Apple. He basically re-branded and re-invented himself through his constant use of Snapchat, which led to many new opportunities, including his 2016 book release The Keys. He’s also close with fellow boss Diddy, becoming the face of the new Ciroc Mango, and generally, promoting Ciroc. Additional deals with brands like Champ Sports and Mentos help bring his earnings to $24 million in 2017, according to Forbes.

Nipsey Hussle

Just as his name would suggest, Nipsey Hussle is all about his hustle. Since as early as 2005, he has been crafting street classics and building an empire, one brick at a time. It’s almost unbelievable to think that Neighborhood Nip still hasn’t released his debut album (that’s another essay, another day). After a brief stint at a major, he decided to venture off to form his own record label, All Money In, of which he remains the CEO, and continues to sign West Coast-based acts. All of his releases since 2010 (among them, The Marathon, The Marathon Continues, Crenshaw and Mailbox Money) have been through his label, while he continues to think up unique and creative ways to get his fans extremely involved in supporting his independent movement.

One such way was via his “Proud to Pay” initiative. The initiative was a call to action for Nipsey fans to shell out the big bucks– the first effort he released via Proud to Pay was Crenshaw mixtape, selling at $100 for a hard copy (as well as some added goodies, including a meet & greet and concert tickets), with online versions still free.99. It worked– he reportedly made $100,000 because of it, with Jay-Z himself supporting the movement, and purchasing 100 Crenshaw hard copies. It was enough to earn him a ranking on Forbes’ 2015 Hip-Hop Cash Kings list, too. He would take things a step further with Mailbox Money. The rapper announced another Proud to Pay campaign, except the price tag was steeper– the hard copies would sell for $1,000 a piece, with only 100 copies being made. Again, he profited, despite also offering it as a free download, he quickly sold 60 copies (we’re unsure if all 100 were sold, ultimately), but just those 60 would earned him a cool $60,000.

Through it all, then, he continues to perfect his hustle, extending his business reach and most importantly, building his community of Crenshaw up at the same damn time. There are videos, from as early as 2008 of Nipsey Hussle speaking facts on business ventures like property development and investment. He recently opened The Marathon clothing store in Crenshaw, after having a t-shirt shop in the same plaza years ago, and as of late he has been heavily consumed in more exotic business ventures like investing in Cryptocurrency and more. Moral of the story, here, is that this guy continues to make a way for himself to acquire capital, independently, and outside-the-box.

They say that if you’re loved where you are from, then you really are a boss, as is the case for Nipsey Hussle, who represents Crenshaw to the fullest. While his networth might not be able to rival anyone else on this list, we salute him for staying true to his city and his ability to take risks. Peep this documentary on the opening of The Marathon clothing store to get more insight to Nipsey Hussle’s rise and unprecedented support and love for his community.

Now all we need is Victory Lap.

Gucci Mane

There are a handful of names in the Hip Hop industry that need no introduction, and Radric Delantic Davis, better know as Gucci Mane, is one of them. During his nearly 15-year run Gucci has managed to release eleven studio albums, countless mixtapes, many of which were released while he was in prison, and establish several record labels including 1017 Brick Squad.

But the true reason Gucci Mane is on this list is the magical year and a half he has had since his release from prison, which he’s used to set himself up for years to come. Truth be told, two and a half, call it three years of incarceration can take its toll on any artist and the rebuilding efforts upon release are often daunting, but not for Gucci Mane, who made it seem all too easy. He released 41 mixtapes between the years of 2013 and 2017, even though he was incarcerated the majority of those years. Additionally, it is estimated that he made $1.3 million dollars in 2014, and again, he was behind bars the full 365 days of that year. These feats alone are rather impressive.

What’s even more impressive, than his dominance behind bars, has to be his efforts as a newly rehabilitated citizen. On his first day as a free man Gucci Mane literally set the streets on fire with his single “First Day Out The Feds,” which was streamed 1.1 million times in the first 24 hours of its release. In the year since his release from prison he has release five projects and received five platinum and gold certifications from the RIAA. He’s also became an author with the release of The Autobiography of Gucci Mane. To top it off, he signed what we can only imagine is a lucrative deal with BET to air his anticipated wedding with Keyshia Ka’ior and a resulting mini TV series. Last week, his most recent album Mr. Davis came in with a solid No. 2 debut on the Billboard 200, and moved the equivalent of 70,000 units.

It doesn’t stop there, though, as one of Gucci’s most-boss habits is the simple fact that he literally never stops working. Gucci Mane announced on October 24th that he had the title for his next album El Gato the Human Glacier, while announcing his goal of earning $10 (mo’) million dollars before he takes a honeymoon with his wife. There’s another key takeaway and learning lesson here: announce your goals, write them down, put them out into the universe, in order to help you fully realize them. Gucci knows what’s up.

Gucci’s networth is reportedly estimated to stand at $20 million.

2 Chainz

College Park, Georgia is like a mecca of sorts for Southern music. Many an influential artist has come out of College Park, one of whom is making a strong case to be considered the best, 2 Chainz, aka Tity Boi. 2 Chainz’s come-up is very unique, he was constantly in motion to better himself.

It all started with the rap duo founded by 2 Chainz, Playaz Circle, and a record deal with Ludacris’ DTP Records. The duo’s 2007 debut Supply & Demand garnered them the most recognition, helped along by their Lil Wayne-assisted street classic, “Duffle Bag Boy.” This was the start of what has proved to be a long and fruitful relationship with Weezy F. Howeveer, by early 2010, then-Tity Boi left DTP Records, in a move to prioritize his solo career, which also marked his name change to 2 Chainz, and the release of his first solo mixtape, T.R.U. REALigon.

Then, before our very eyes, we began to see the reign of 2 Chainz unfold. Chainz, who already had a healthy amount of mixtapes under his belt as Tity Boi, would go on to lock in an unprecedented amount of features — an amazing strategy, that ultimately made it so his name was simply unavoidable between 2011 and 2013. He would sign a deal with Def Jam Records in 2012, and released his debut album Based on a T.R.U. Story that same year, debuting at No. 1 spot on the Billboard 200 — proving all his hard work paid off (or, at the very least, creating a nice fanbase). The next several years 2 Chainz utterly crushed it, releasing several projects including his collaborative album with Lil Wayne, ColleGrove and what may be his best album yet, Pretty Girls Like Trap Music. The album is already gold, and Chainz has already announced his next one is well on the way.

His work ethic then, is perhaps only rivaled by Gucci Mane. In our digital cover story, he explained it — how he stays in the studio from dusk til dawn, and actually does work at improving himself. In the midst of his constant music releases, he’s also managed to make an estimated $2 million off the infamous “Dabbing Santa” sweatshirt, for his brand CEO Millionaires, in addition to establishing his record label The Real University that is home to artists like Cap 1, Skooly, Fresh and C White (he’s putting on for Atlanta too, creating opportunities for those around him in his city).

As you can tell, there’s literally no stopping 2 Chainz– when he broke his leg in the middle of his Pretty Girls Like Trap Music Tour, he continued to tour by performing in a (pink) wheel chair. 2 Chainz possesses the type of determination, vision and innovation that any boss needs to run shit and quite frankly, how can you not salute that?

Chance The Rapper

Before we even get into this breakdown, we honestly have to pull one of those “going to just leave this here,” moments, with what is quite possibly the most precious and inspiring videos on the Internet. A few days ago, Chance The Rapper aka Lil Chano From 79th, tweeted a series of videos featuring him and his photo-bombing daughter opening the three Grammy awards he won this past year. In the video, Chance appears to get emotional, and rightfully so, because what a magnificent journey it has been for him.

To think that this entire journey started with Chance The Rapper and his manager Pat Corcoran, in a Hooters over four years ago is almost surreal. At the time, Corcoran was a DePaul University student working on the booking side of things, securing gigs for collective These Days, which was comprised of Vic Mensa, Donnie Trumpet and more. Chance The Rapper was still in high school, and began to trend worldwide after he released his 10 Day mixtape, infamously the creation of a 10-day suspension from school. It was a slow build prior to the tape, but the tape pushed his budding career up a notch. Chance had everyone from Childish Gambino to L.A. Reid reaching out to him, soon enough. He and Corcoran went on countless label visits and sat through a number of meetings for record deals before realizing that this was not the route they wanted to take.

Ultimately, the journey makes a true turning point after the release of Chance’s critically-acclaimed mixtape Acid Rap, when he and his team began planing for his third full-length mixtap Coloring Book. Chance was now in a position to exercise the influence of his weight in the game, and he did just that, with Coloring Book released exclusively on Apple Music, and debuting on the Billboard 200 based purley off streams– unheard of at the time. He would go on to win Best Rap Album at the 2017 Grammys, earning him another record, as the first stream-only album to win a Grammy.

His story is gratifying in so many ways, from the ground-breaking nature of his work, to his constant humility, genuine generosity and innovation. Not to mention all that he’s doing for his city of Chicago, giving hope to city dwellers, where there otherwise might be none. Whether he is donating $2 million to Chicago Public schools or urging the youth to express themselves, or else, throwing The Magnificent Coloring Day Festival for his city exclusively, before turning it into a world tour. Beyond this, he’s made sure to keep his pockets healthy, as any boss would, by locking in campaigns with Kit Kat, fashion giant H&M, and a constant round of festivals and tours. The rapper reportedly earned $33 million in 2017 — without ever selling a hard copy of an album. That’s millennial, if ever there was.

Chance is the people’s champion, a new type of boss.

Who do you think is the biggest boss on this list, though? Shout them out in the comments.

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