Whether it happens at the biggest casinos in Las Vegas, a neighborhood sports bar or a backyard barbecue, gambling on sports is big business. Over the years, some of your favorite rappers have either secured or parted with some major bags betting on athletic events.

When it comes to a safe bet, Floyd Mayweather has been a guaranteed pay, as a number of rappers have collected coins in Vegas by placing bets on the undefeated boxer. Easy money. But sometimes things gets personal.

Drake recently won a bet with the Migos' Quavo over the outcome of the 2018 College Football National Championship game between the University of Alabama and the University of Georgia. 'Bama ended up winning in overtime, but Drizzy only took home bragging rights—Huncho claims it was just a friendly bet and no money changed hands. Still, both rappers have a history of chancing some major coin on sports.

While Drizzy has been known to bet big money on the teams he favors, others take their wagers even further. When it comes to rappers who seem to have no problem betting the GDP of a small third-world country on a big game, Birdman has proven over and over that he’s willing to risk it all. Snoop, on the other hand, accepts a whole different type of green as payment for debts.

They definitely aren’t the only ones. JAY-Z, 50 Cent, Diddy, French Montana, Migos, Snoop Dogg and more have all publicly taken wins and losses trying to make a quick come-up gambling on sports. It's a tricky game.

With so much money switching hands over what goes down on the gridiron, ring or hardwood, XXL decided to follow the paper trail and revisit some of hip-hop's most memorable—and high-stakes—sports bets.