Plaxico Burress seemed destined for success in the NFL. The wide receiver was drafted by the Pittsburgh Steelers in 2000, giving them several productive seasons before signing a free agent contract with the Giants in 2005. In New York he approached superstardom, playing on the 2007 squad that downed the mighty Patriots in Super Bowl XLII and even making the game-winning catch. But unfortunately, that highlight would be among his last due to a 2008 incident that would be tragic if it weren’t so ridiculous.

While in a crowded nightclub, Burress managed to shoot himself in the right thigh while fiddling with a gun in his pocket. To add insult to literal injury, the gun was illegal, which meant a potential 15-year prison sentence. The Giants immediately suspended Burress without pay for the boneheaded move, and he wouldn’t play another down for the team. 

He ended up serving 20 months, eventually finishing out his career with the New York Jets and back with the Steelers. But he found himself in hot water once more in 2015 for failure to pay over $50,000 in taxes. This earned him five years’ probation, with the possibility of going back to jail if he fails to pay up — but that would really be shooting himself in the, er, foot.

By sheer numbers, Darryl Strawberry’s Major League Baseball career looks like one that any player would envy. He played 17 seasons beginning in 1983, was a member of four world championship teams, and logged 335 home runs and 1,000 RBIs. Of course, there are other numbers as well. During those 17 seasons, there were two domestic violence arrests, three drug-related suspensions, and one tax evasion conviction. 

As if his personal problems weren’t enough, Strawberry was diagnosed with a cancerous tumor in 1998, which was removed. He was set to attempt a comeback in 1999, but was derailed by an incident of drug-fueled prostitute seeking while training with the Yankees’ AAA club in Tampa. Authorities said Strawberry yelled something unintelligible at an undercover officer before circling the block and approaching said officer to offer $50 for sex acts. Compounding his bad decision was his cocaine stash, which was cleverly wrapped up in a $20 bill. 

Despite his forlorn expression in his mugshot, he was given only a four-month suspension, and returned to help the Yankees earn yet another championship. But that season would be his last, as during the offseason he tested positive for cocaine. Strawberry apparently finally learned his lesson, as today he runs a ministry dedicated to helping drug addicts.

Freakishly gifted wide receiver Randy Moss spent most of his career with the Minnesota Vikings, and though his physical gifts were obvious, he had a hard time shaking a reputation for being a bit of a pothead. He’d been in trouble over the weed before entering the NFL in 1998, and it didn’t help when cops found a joint in his car after an incident in 2002. Of course, this was after he’d pushed a traffic officer’s car a half block down the street with his own car, which was a bit more serious.

He was eventually only charged with a pair of misdemeanors for the traffic incident and another for the weed. However, the incident didn’t keep him from continuing to partake of the ganja throughout his long career, which the NFL just kind of grudgingly tolerated as long as he kept making mind-bending catches.

Ex-Raiders and current Browns tackle Desmond Bryant wasn’t exactly a household name in 2013, and his arrest may have gone under the radar of the general public if not for one detail. Sure, it was a pretty funny story — Bryant randomly showed up at a neighbor’s at the crack of dawn, shirtless and stinking drunk, and caused some kind of commotion. But it wasn’t the details of the offense that the whole Internet wanted to discuss — it was what the hell was going on in his mugshot.  

Speculation has been endless. Is he lying down? Being punched in the back of the neck? Turning into a walrus? The possibilities were endless, and before the hapless Bryant knew it, Jimmy Kimmel was using him as a punchline and “Dezzing” had become a meme. 

A mortified Bryant, who incidentally is a Harvard graduate with a major in psychology, quickly bolted from Oakland to sign a free agent contract with the Browns, which fortunately had been in the works anyway. At his introductory press conference, he said: “I think in time I’ll be able to show you guys… that’s really not indicative of me. It was an accident. I’ve moved beyond that and hopefully everybody else will be able to.”