Rappers have come a long way over the years. They started out at fringe artists making controversial music that opened the eyes the world to the plight of inner cities. The mainstream was kind of afraid of them. But the kids listened anyway, and so giant record labels made them rich. Now they mostly make songs about drinking expensive liquor and driving fancy cars. And of course, they’ve become some of the smartest business people around, having learned to make money off of anything and everything. Thus, even if you lament the current state of hip hop music, you still have to respect the business acumen of the genre’s movers and shakers. So today we’re doing just that—showing our respect for hip-hop’s movers and shakers by doing this list of the richest rappers in the world.

Enjoy!

Net Worth: $25M

He may be 36 years old, but Rick Ross is just starting to hit his stride in terms of making money. His fourth studio album, Teflon Don, was his most commercially successful one to day, and the critics loved it too. Moreover, he released it on his own label—Maybach Music Group. (Yes, apparently he named his record company after a luxury automobile.) And of course, lets not forget his other sources of income—an endorsement deal with Reebok and an significant investment in Wingstop franchises.

Yeah, he looks like a dude who frequents Wingstop.

Net Worth: $30M

T.I. lost most of his lucrative endorsement deals with companies like Rémy Martin Cognac and AXE body spray after being convicted of possessing three unregistered machine guns. However, by the time he went to jail in 2009, he’d already made a killing. And of course, his pre-incarceration album Paper Trail was a huge hit, making him a few bucks.

Net Worth: $45M

Hey, remember when Andre 3000 was part of one of the best acts in hip-hop? Yeah, that was nice. But alas, Outkast is no more, and now Big Boi is the only one making music. Of course, Big Boi isn’t on this list, and he doesn’t have a lucrative endorsement deal with Gillette, so maybe Andre 3000 was right to focus on his acting career.

Net Worth: $55M

Most of Nelly’s money comes from record sales. He was, you’ll recall, one of the top-five selling artists of the 2000s, which means he still has a pretty decent cash flow. However, Nelly’s had a few endorsement deals (with Ford, for example), plus a few acting gigs.

Net Worth: $60M

Busta made a lot of money on his endorsement deal with Pepsi. Of course, judging by his current physique, I’d say the deal also included a lifetime supply of the sugary beverage. But hey, with all that money he can afford angioplasty down the road. He’s also still making serious money with his music. In 2010, a collaboration with Chris Brown on “Look at Me Now” made him a pretty penny, and did his excellent work on DJ Tiesto’s dance track, “C’mon (Catch ‘Em By Surprise).”

Net Worth: $65M

At some point, ever rapper has the same epiphany, and it does something like this: “wait, I have to bust my ass in the studio and on the road just to make $10M, while movie starts make $10M working 2 or 3 months on a movie? I need to get in on that.” So, yeah, that’s what Christopher “Ludacris” Bridges did. From 2004-06, he appeared in one film a year. Then from 2007-11 he appeared in two films a year. So his acting career has really taken off. Of course, he’s also still doing well in the music business, having learned the lesson that every other famous rapper has earned: it pays more to “collaborate” and get writing credits on hit singles than it does to produce entire albums of your own.

And of course, then there are the endorsements: he reps for TAG body spray and Conjure Cognac, and he’s co-owner of Soul headphones.

Net Worth: $75M

Swizz Beats actually started his own label, Full Surface, long before he ever made an album of his own. And Kanye West called him the greatest hip-hop producer of all time. So, that’s something. As for other sources of income, he’s got big endorsement/designer deals with Kidrobot and Reebok, as well as a lucrative deal as a spokesperson for Lotus and Microsoft’s Bing serch engine.

Net Worth: $75

From about 2005-2008, almost every song you heard on the radio sounded the same. And that’s because, during that period, almost every song you heard on the radio was either co-written or produced by Timbaland. Nelly Furtado, Justin Timberlake, Madonna, Flo Rida, Pussycat Dolls, Jennifer Hudson, Bjork, Jay-Z, 50 Cent, Dr. Dre, New Kids on the Block, Keshia Chante, Drake, Katy Perry, Akon—they’ve all worked with Timbaland. And that’s why he’s filthy rich.

Net Worth: $77.5M

Pharrell hasn’t had any huge megahits himself as an artist, but as part of the Neptunes he has produced a few…you know, like #1 songs “Slave 4 U” by Britney Spears and “Hot in Herre” by Nelly. And then he’s also won a few Gammys for his work on Justin Timberlake’s Justified and the Ludacris song “Money Maker.” And…blah blah blah…Jay-Z…blah blah blah Snoop Dog. You get the idea: he’s a major producer.

In addition to his music skills, though, Pharrell is also one of the most stylish men alive (at least if you listen to the folks at Esquire), and that makes him an endorsement magnet. So, yep, that’s why he’s rich.

Net Worth: $80M

In the 1990s, LL Cool J endorsed FUBU, and FUBU became one of the biggest clothing lines on the planet. So that really helped his financial outlook. Then he transitioned from rapping to acting, and that improved his financial outlook even more. Today the guy is as big a star as ever, and of course the ladies still love Cool James.

Net Worth: $90M

Kanye is kind of a douche, but he’s a talented douche and, consequently, a very rich douche. Though he lost some major endorsements after the whole Taylor Swift thing, he still makes some money from Nike (for whom he designed the Nike Air Yeezy II), and he still has his own high-end women’s clothing line and his own label (G.O.O.D. Music). Oh, and he still makes very popular music.

Net Worth: $95M

In September, Lil’ Wayne surpassed Elvis Freaking Presley to become the male performing artist with the most entries on the Billboard Hot 100 chart with his 109th song. Of course, not all of those were his songs alone, and therein lies Lil’ Wayne’s genius: he makes money by being on everyone else’s records, too. Also part of Weezy’s genius: cross-promotional marketing—by which I mean the fact the he name-drops his own products (like Trukfit skateboards) in his songs. Plus, he’s also got big endorsement deals with companies like Mountain Dew. So, yeah, Lil’ Wayne is doing just fine.

Net Worth: $100M

If you told me 20 years ago that Ice Cube, one of the original gangsta rappers, a guy who made a song called “Fuck tha Police” with the group N.W.A., would be in family comedies called Are We There Yet and Are We Done Yet…I wouldn’t have believed you. But here he is today with 28 film credits as an actor and 19 as a producer or writer. So, while he doesn’t really much street cred anymore, he does have an excellent credit rating.

Net Worth: $110M

Now here’s a former gangta rapper who’s managed to transform his image without losing his cool. I don’t know how he did it, but he did. I mean, the guy is still a huge proponent of week and porn, and yet he also endorses everything from Norton Antivirus software to EA Sports’ FIFA Soccer 13. Oh, and he still makes hit songs. I’m pretty a marketing student could do a PhD thesis on this guy’s career.

Net Worth: $115M

Birdman’s own records weren’t that successful relative to other acts on this list, but, you know, he did start Cash Money Records with his brother back in 1991. Then they signed Lil’ Wayne when he was just 9-years-old and rode that train all the way to the top. Eventually they were bought by Universal, which made Birdman (Bryan Williams) and his brother Ronald a lot of money.

Net Worth: $120M

Eminem obviously has his own label, Shady Records, and he has a few endorsement deals (most notably with Chrysler). But most of Marshal Mathers’s fortune comes from record sales and royalties. After all, he was the #1-selling music artist of the 2000s, and he kicked off the 2010s with a bang with Recovery, 2010′s top-selling (but kind of boring) album.

Net Worth: $250M

In 2007, 50 Cent signed one of the biggest celeb endorsement deals of all time: $100 million to shill Vitaminewater. Of course, even without that deal, he’d still sit at #4 on the list, even though he hasn’t had an album since 2009. The guy is just one of the kinds of endorsements.

Net Worth: $270M

He was an original member of seminal rap group N.W.A., then he co-founded Death Row Records with Suge Knight, and they signed acts like Snoop Dogg, 2Pac, MC Hammer, and, of course, Dr. Dre himself. Then he became a producer and propelled Eminem to stardom, and now his name is on the most popular headphones in the world. Oh, and those headphones—Beats by Dre—they were just sold to HTC.

Actually, I’m surprised this dude doesn’t have more money.

Net Worth: $475M

If there’s anybody out there who could supplant the #1 guy on this list, it’s Jay-Z. Not only does he still sell tons of records, and not only did he co-found Rocawear, and not only does he own bars and clubs and serve as a spokesperson for, like, everything. This guy is also basically the King of New York—the coolest dude in the coolest city in the world. He became a minority owner of the New Jersey Nets by investing $1 million back in 2005. Now, with a cool new location (Brooklyn), a state-of-the-art arena, and a sick new look, they are on the verge of becoming the coolest sports franchises in the world. And it’s all because they are Jay-Z’s team.

So on paper, Jay-Z may only be worth $475M. But he’s going to make so much more than that in the next few years as his brand gets bigger and bigger.

Net Worth: $550M

Though Jay-Z may soon overtake him, Diddy is still the richest rapper in the world. He is the first real hip-hop mogul, with interests in everything from music and fashion (Sean John) to booze (Ciroc Vodka), marketing, cable television, and technology. Does he still have the same street cred as Jay-Z? No, not quite. But there’s no way he cares.