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.

  • Super Bowl XLV, Green Bay Packers vs. Pittsburgh Steelers (2011)

    Stakes: $1 million
    Outcome: Packers win
  • NBA Finals, Miami Heat vs. Dallas Mavericks (2011)

    Stakes: $2 million
    Outcome: Mavericks win

    After LeBron James took his talents to South Beach in 2010, Birdman went all in on the Miami Heat in the NBA Finals. He ended up losing a lot of cash money—2 millies to be exact.

    Brayn Bedder, Getty Images
  • Super Bowl XLVI, New England Patriots vs. New York Giants (2012)

    Stakes: $5 million
    Outcome: Giants win

    You can always count on Tom Brady and the New England Patriots in the big game, right? Not versus the New York Giants in the Super Bowl. Brady's second SB loss to the G Men in 2012 cost Birdman a whopping $5 million.

    Dana Droppo
  • Floyd Mayweather Jr. vs. Canelo Alvarez (2013)

    Stakes: 1 lb. of weed
    Outcome: Mayweather wins

    In typical Snoop Dogg fashion, the Cali legend bet a pound of weed on the 2013 bout between Floyd Mayweather Jr. and Canelo Alvarez, with a man he simply named, Lui. Of course, Mayweather won, and Snoop secured the bag.

  • NCAA Men's Basketball Final Four, University of Kentucky vs. University of Wisconsin (2015)

    Stakes: $6,000
    Outcome: Wisconsin wins

    In 2015, The Game and Drake put up chips on the Final Four matchup between the University of Kentucky and the University of Wisconsin. The Badgers ended up beating the perennial powerhouse, and Chuck wasn't shy about boasting of his come-up on social media.

     

  • Canelo Alvarez vs Miguel Cotto (2015)

    Stakes: $100,000
    Outcome: Canelo wins

    In 2015, JAY-Z lost six figures betting with Oscar De La Hoya on a boxing match that featured his Roc Nation Sports client, Miguel Cotto. Jigga donated the money to a charity of De La Hoya's choice.

    Robert Kama, Getty Images
  • Floyd Mayweather Jr. vs. Manny Pacquiao (2015)

    Stakes: $250,000
    Outcome: Mayweather wins

    Diddy bet Mark Wahlberg $250,000 that the fast talking, lavish-life living, undefeated champ, Floyd Mayweather Jr. would be the last man standing in his bout with Manny Pacquiao, in 2015. He was right.

  • Floyd Mayweather Jr. vs. Manny Pacquiao (2015)

    Stakes: $1.6 million
    Outcome: Mayweather wins

    Everyone seemed to want in on the "Fight of the Century" between Floyd Mayweather Jr. and Manny Pacquiao, including resident Money Team MC, 50 Cent, who bet $1.6 million on the bout.

    Paul Zimmerman, Getty Images
  • NBA Finals, Golden State Warriors vs. Cleveland Cavaliers (2016)

    Stakes: $60,000
    Outcome: Cleveland wins

    French Montana and Drake put a friendly wager on the 2016 NBA Finals. In the end, Drizzy had to come up off 60 bands when the Cavs pulled off the improbable victory.

  • Super Bowl 50, Carolina Panthers vs. Denver Broncos (2016)

    Stakes: $75,000
    Outcome: Broncos win

    Migos rode with Atlanta native Cam Newton in Super Bowl 50, wagering 75 racks on the game. Unfortunately, it didn't end well for either party.

    Paras Griffin, Getty Images
  • Super Bowl LI, Atlanta Falcons vs. New England Patriots (2017)

    Stakes: $50,000
    Outcome: Patriots win

    There were a lot of sick Atlanta Falcons fans after Super Bowl LI. Offset's pockets were 50 stacks lighter following the epic collapse by the Dirty Birds, having placed multiple bets, including $10,000 with Blac Youngsta.

    Bennett Raglin, Getty Images
  • CFP National Championship, University of Alabama vs. University of Georgia (2018)

    Stakes: $0
    Outcome: Alabama wins

    Drake and Quavo put a non-monetary wager on the 2018 College Football National Championship and when the Georgia Bulldogs lost, Drizzy came a callin'.