The 8 Greatest Tattoos That Were the Result of Losing a Bet

The initial heartbreak that comes with losing a bet can be pretty tough, but having a permanent reminder of that failure inked into your flesh can be damn near soul-crushing.

Here are our eight favorite stories of wagers that resulted in the loser having to get a tattoo of the winner’s choice.

Tattoo League loser forced to get Matthew Berry/Miley Cyrus tattoo.
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Some fantasy football leagues require the guy who finishes dead last to cough up an extra 25 bucks. Others make the guy at the bottom of the standings shave his ass or something to that effect. But a crew of fantasy dorks in Omaha take it one step further and make the loser of the “Tattoo League” get an ink job that is decided upon by the nine other guys in the league. Following the 2013 fantasy season, this poor guy had to get a tat of Matthew Berry impersonating Miley Cyrus riding a wrecking ball. Damn, son.

Broncos fan forced to get “Tebow Time” tattoo.
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In 2011, Juan Contreras and Josh Lucero decided to bet on whether or not Tim Tebow would win five games as the starting quarterback for the Denver Broncos. Contreras thought Brady Quinn was the man while Lucero thought Tebow was pretty much the second coming of Christ. If Lucero would have lost, he would have been forced to get a “Te-Blows” tattoo. But Tebow went 6-1, and it was Contreras who had to sport this gem instead.

Sad Oregon fan forced to get Ohio State tattoo after 2015 national championship beatdown.
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By the looks of his Twitter page, @Debellonia88 lives and breathes Oregon football. His backdrop features several Oregon players in a huddle, and a recent retweet of his is a breakdown of Oregon’s “Signing Day.” But his love of Ducks football is also responsible for his most recent tattoo: the Ohio State logo on his right leg that he was forced to get after betting his Ducks would win the first ever College Football Playoff Championship Game this year. They obviously did not. Not even close.

Dude gets awful Sopranos family tattoo on his back after betting they would die in the series finale.
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It’s never a good sign when the producers of a show called “America’s Worst Tattoos” give you a call, but in this case, David totally deserved his fate. The bet was that David would get a tattoo of America’s favorite mob family if they didn’t die in the finale. That’s it. As his friend put it, “This was a one-sided bet. Either he loses or gets nothing.” Geez. Here’s to hoping this guy opens up a sports book one day.

British man gets Andy Murray tattoo on his ass after winning a bet with his friends, but they all had to get his name tattooed on their bums.
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“Sopranos” David may take the cake for stupid bet, but this will probably go down as one of the strangest bets of all time. In 2013, William Hirons bet his “mates” that if Andy Murray beat Novak Djokovic in the Wimbledon final, he would get a tattoo of Murray on his left butt cheek. In return, every friend would have to get Will’s name inked into their posteriors. Murray won the match, but we’re still not sure who actually won this bet.

Red Sox fan gets Yankees logo tattooed on his ass after Yankees win 2009 World Series.
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Red Sox fan Cliff Stewart made a bet with a Yankees fan sometime post-2007 in which he would get a Yankees tattoo on his rear end if the Yankees would win another World Series before the Red Sox. It must have seemed like a genius bet at the time, as the Sox had won the Fall Classic in both 2004 and 2007. But New York won it all in 2009, and Stewart was forced to drop his drawers and take his punishment like a man.

Broncos fan gets Bill Belichick’s name tattooed on his back after Brady defeats Tebow.
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What is it with guys risking real estate on their bodies with Tim Tebow at the helm? If Tebow would have pulled off the miracle of miracles and beaten the Patriots in their 2011 regular season matchup, Broncos fan Brady Wagner would have watched his friend, a Patriots fan, get a Tim Tebow tattoo. That didn’t happen. In fact, the Patriots won by 18 points that day, so Wagner had to get New England’s head coach’s name inked into his lower back instead.

Guy gets tattoo of “unicorn surrounded by penises” after losing bet with tattoo artist.
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Suddenly, losing 200 bucks on the Super Bowl doesn’t seem like such a travesty. Some guy on Reddit offered up a free lesson last year titled “Don’t lose a bet to a tattoo artist.” The reason? You guessed it: You’ll wind up with a unicorn surrounded by colorful dicks inked into your skin. A similar bet allegedly took place five years earlier in which the guy receiving the unicorn and penises tat was also tased midway through the ink job. What the hell is wrong with you people?

Tramp Stamps are usually a bad idea, but these are beyond pathetic: The 17 Worst Tramp Stamp Tattoos You Will Ever See