The Most Ridiculous Celebrity Sports Bets in Recent History

50 Cent and Birdman aren't the only ones putting up seven figures on a game.

February 5, 2012

Complex Original

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Intro

With Super Bowl XLVI's kickoff less than 24 hours away, gamblers everywhere are scrambling to place their final bets on the big game. Currently, the Patriots are three point favorites, but fans can bet on everything from the color of Gatorade that'll be dumped on the winning coach to the number of times Gisele Bundchen will appear on the screen.

This is the time of the year where just about everyone looks to flip a buck on a quick bet and high-rolling celebs are no exception. The latest example being 50 Cent's $1 million challenge to Birdman on the Giants beating the Patriots. Birdman had previously said he'd put down $5 million on the Patriots and that he was looking for takers. But Baby and Fif's possible seven-figure wager is just the latest in the recent trend of celebs publicly betting money on everything from $1,000 on a game of one-on-one with Kobe Bryant to $1.25 million on a few rounds of golf. So, before you place your wagers on tomorrow's big game, check out A Recent History of the Most Ridiculous Celeb Sports Bets.

The Costliest Celeb Bet of All Time

Celeb(s): Pete Rose
When: 1987
Wager: $2,000-$10,000
Event: 52 Reds Games during the 1987 MLB Season

In a 2007 interview with Dan Patrick and Keith Olbermann on ESPN Radio, Pete Rose finally confessed to the worst kept secret in major league baseball: he was betting on his team's games. But what people probably didn't see was how bad his gambling problems actually were. "I bet on my team every night. I didn't bet on my team four nights a week. I was wrong," Rose said. "I bet on my team to win every night because I love my team, I believe in my team." So when the Reds caught an L, Charlie Hustle wasn't just feeling the agony of defeat, he was also feeling the agony of deplete in his wallet. If that weren't bad enough, his gambling is also what led to his lifetime ban from the sport. SMH. Some things ain't worth it, fam.

Even Mr. Las Vegas Has Off Days

Mr. Las Vegas Is On One

Celeb(s): Bob Stupak a.k.a. Mr. Las Vegas
When: 1/22/1989
Wager: $1M
Event: Super Bowl XXIII: Cincinnati Bengals vs. San Francisco 49ers

When you're nicknamed "Mr. Las Vegas," it's very likely that you know your shit. In one of the biggest reported Super Bowl payouts came when Bob Stupak—a casino owner and professional gambler—placed a $1 million bet on Super Bowl XXIII where he took the underdog Cincinnati Bengals over the seven-point favorites, the San Francisco 49ers. Unfortunately, the Niners ended up winning the game, 20-16. We gotta give it up to Stupak to living that "go big or go home" lifestyle.

MJ Stays Losing?

Celeb(s): Michael Jordan
When: 9/20/1991
Wager: $1.25M
Event: Golf

According to Michael & Me: Our Gambling Addiction . . . My Cry For Help!, author Richard Esquinas claimed that he and Jordan faced each other in a golf match at Aviara Golf Course in San Diego County that resulted in MJ losing a grand total of $1.25 million! But it didn't end there, over the course of their four-year relationship, Equinas took an additional hundreds of thousands of dollars from Jordan's deep pockets. Hey Mike, just a suggestion so hear us out, but maybe you should cut your losses before they hit seven figures. #gamblerproblems

B-Hop Invests In Himself

Celeb(s): Bernard Hopkins
When: 9/29/2001
Wager: $100,000
Event: Himself in his Middleweight championship bout vs. Trinidad

Before getting in the ring with Felix Trinidad, Bernard Hopkins was approached with an offer by GoldenPalace.com to earn some extra pocket change. In exchange for wearing a henna tattoo, the Web site would give him a cool $100K. Not one to turn away some easy cash, The Executioner agreed and used the money to bet on an upcoming fight where a boxer was considered a 4-1 underdog. That boxer was himself. In the aforementioned bout, Trinidad lost in the 12th round by TKO, which meant that Hopkins not only won the WBA Super Middleweight title but he also pocketed an additional $400,000 on his side bet. Who says you can't have your cake and eat it too...then have seconds?

Charles Barkley Saw The Pats Dynasty Coming

Celeb(s): Charles Barkley
When: 1/3/2002
Wager: $550,000
Event: Super Bowl XXXVI: New England Patriots vs. St. Louis Rams

Before developing into a dynasty in the 2000s, the New England Patriots were 14-point underdogs to the St. Louis Rams and "The Greatest Show on Turf" in Super Bowl XXXVI. Nowadays, the Patriots not being favored in a championship game seems foreign to us. Sorry, G-Men. But Charles Barkley took a chance on the Pats when he placed a bet in Vegas worth $550,000. New England ended up defeating St. Louis, 20-17. That's cool and all but this win doesn't make up for all the Ls dude took over the years.

Phil Proves That Nice Guys Can Finish First

Celeb(s): Phil Mickelson
When: August 2000
Wager: $20,000
Event: Baltimore Ravens 2000 season winning the Super Bowl

Before the start of the 2000-2001 NFL season, golfer Phil Mickelson placed a $20,000 bet on the Baltimore Ravens, who happened to be 28-to-1 underdogs to win the Super Bowl. The reason? "I liked their off-season player acquisitions." Much to everyone's surprise (except for the clairvoyant Mickelson), the Ravens ended up defeating the New York Giants, 34-7, in Super Bowl XXXV. Mickelson ended up taking home $560,000. #racksonracksonracks

Chuck Pucker's Up

Chuck Has to Pucker Up

Celeb(s): Kenny Smith and Charles Barkley
When: November 2002
Wager: Kiss Kenny's ass on Inside the NBA
Event: Whether or not Yao Ming Could Score 20 points during the 2002-03 season

Not one to turn down a bet, Charles Barkley had a wager with his TNT colleague, Kenny Smith, that Yao Ming would not score 19 points in a game And to sweeten the pot—we use that term very lightly—Barkley agreed to kiss Kenny's ass if he lost. Later that week, Sir Charles' worst nightmare came true when Yao dropped 20 on the Lakers. The following week on Listen Up! With Charles Barkley and Ernie Johnson, Barkley repaid his debt with a little twist: he kissed the rear end of a donkey that Smith brought into the studio. The only thing that could've made this moment even better is if Kenny threw th is on right afterward.

What's a Bromance Worth?

Celeb(s): 50 Cent
When: 5/5/2007
Wager: $1M
Event: Floyd Mayweather vs. Oscar De La Hoya

50 Cent and Floyd Mayweather's bromance has been going on for a few years now. The G-Unit general has made cameos on Floyd's episodes of 24/7, they buy each other extravagant gifts, and spend a lot of down time together. So, when it came time for Money May to face Oscar De La Hoya, Fif not only showed his support by rapping during Mayweather's entrance but he also bet $1M on his friend. 50's faith paid off when Pretty Boy Floyd won by split decision.

Rap's Heavyweight King Puts a Milli on the Champ

Rap's Heavyweight King Puts His Money on the Champ

Celeb(s): Rick Ross
When: 5/7/2011
Wager: $1M
Event: Manny Pacquiao vs. Shane Mosely

Ricky Rozay doesn't fuck with Floyd Mayweather and has been known to give Manny Pacquiao shout-outs on wax. So, when it came time to Pacman to face Shane Mosley, Ross visited the Filipino boxer at his gym and reportedly bet $1M on the fight. Manny cruised to a win by unanimous decision and the Boss had another thing to grunt about in 2011.

The Dumbest Celeb Sports Bet Ever

The Dumbest Celeb Sports Bet of All Time

Celeb(s): Bow Wow vs. Kobe Byant
When: 7/11/2011
Wager: $1,000
Event: One-on-One: Kobe vs. Bow Wow

Now what idiot celeb is dumb enough to bet a stack on themselves in a one-on-one game against Kobe Bean Bryant? Yes, that would be Bow Wow. Not only did he lose, Bow Weezy failed to even score a point against the 5-time NBA champion. Somehow we think this was more of a promotion ploy for his next album (release date Nevuary 2013) more than anything else. Nice try, Shad.

Snoop Loves the Kids

Celeb(s): Snoop Dogg vs. Donnie Wahlberg and Dana White
When: June 2010
Wager: $20,000
Event: 2010 NBA Finals: Los Angeles Lakers vs. Boston Celtics

When it comes to dedicated celeb sports fans, Snoop Dogg is up there with the best of 'em. From his 1967 Pontiac tricked out with a Laker paint job and interior to his regular appearances at Lake Show home games, the Doggfather reps pretty hard. So, Snoop let his money do the talking when he bet both Donnie Wahlberg and Dana White $20,000 that his Lakers would win the 2010 NBA Finals against the Boston Celtics. The money won would go to a charity of the winner's choice. It was a close one but Lake Show won the 2010 NBA Finals in a thrilling seven-game series. Seems like there were no real losers on this one.

Young Mula, Baby!

Celeb(s): Birdman
When: 2/6/2011
Wager: $1M on Green Bay Packers
Event: Super Bowl XLV: Pittsburgh Steelers vs. Green Bay Packers

They don't call dude the No. 1 Stunna for nothing. When Super Bowl XLV rolled and and Weezy's favorite team was in the big game, Baby put a milli down on Green Bay. Aaron Rodgers & Co. held on to win 31-25. Baby money? We don't think so, Jay.

Birdman Takes His Loot to South Beach

Celeb(s): Birdman
When: June 2011
Wager: $2M
Event: 2011 NBA Finals: Miami Heat vs. Dallas Mavericks

After putting up a $1M on the Packers in Super Bowl XLV, Birdman decided to up the ante just a few months later when he bet $2M on the Heat in the 2011 NBA Finals vs. the Dallas Mavericks. Things were looking pretty good with the Heat up 2-1 in the series then Dirk & Co. came alive and went onto win the series 4-2. If you think losing $2M would cause Baby to go sulk in one of his Maybachs, you're wrong. Birdman and Wayne were out partying with the Mavs that night. #helluvalife

Money May Lives Up to His Name

Celeb(s): Floyd Mayweather, Jr.
When: 1/14/2012
Wager: $1M
Event: AFC Divisional Playoffs: Denver Broncos @ New England Patriots

When it comes to degenerate athlete gamblers no one is seeing Floyd Mayweather, Jr. right now. The boxer—who lives in Las Vegas—regularly posts winning receipts onto his Twitter. He'll bet a couple hundred grand on everything from a half of regular season college basketball to NFL playoff games. While everyone was riding the Tim Tebow bandwagon heading into the divisional playoff game between New England and Denver, Mayweather felt pretty confident that Timmy was out of miracles. So confident that he put seven figures on it. We only have one issue with Mayweather and these receipts—we've yet to see a slip for his losses. Just don't end up on this lis t, homie.

Fif Goes With the Home Team

Celeb(s): 50 Cent
When: 1/22/2012
Wager: $500,000
Event: 2012 NFC Championship: Giants @ 49ers

The rapper who claims he runs New York bet 500 stacks on the G-Men as they faced the San Francisco 49ers in the NFC championship. Thanks to some clutch plays by Eli Manning and a couple epic fails by Kyle Williams, 50 cent added to his fortune. After this win, Fif decided to challenge Baby to a $1M bet on the Super Bowl and a fan to the most pause-worthy wager we've ever heard of. Reason No. 1,456 to root for the G-Men tomorrow.