In April, for example, he threw a porn actress from a roof into a pool while she was naked during an adult magazine photo shoot. She broke her foot and threatened to sue him.
He wasn't charged, but video of the incident and a sarcastic letter from Bilzerian's lawyer to the actress's attorney garnered heaps of attention.
The letter, signed by lawyer Tom Goldstein and posted online by celebrity news website TMZ, said the actress willingly signed up for the stunt. Goldstein suggested she gather up all her belongings and prepare to give them to Bilzerian if she sued, because he would likely win.
"Then he will probably blow it up with a mortar in the desert," Goldstein wrote.
Blowing things up in the desert is what may have landed Bilzerian in jail this week.
The 34-year-old dubbed the "King of Instagram" after amassing millions of followers was arrested Tuesday night at Los Angeles International Airport on a Las Vegas warrant accusing him of possessing bomb-making materials.
Bilzerian was released Wednesday and is scheduled to appear in Las Vegas Justice Court on Jan. 9 to face two felony counts. If convicted, he could face up to 6 years in prison and a $5,000 fine for each count.
His lawyer, David Chesnoff, had no comment except to say Wednesday that Bilzerian and Jeremy Guymon, who is also charged with possessing explosive materials, were looking forward to their day in court.
Bilzerian's popular Instagram account is consistently filled with photos of a playboy lifestyle: private jets, scantily clad women, piles of cash, guns, and Bilzerian shooting those guns in the desert.
The criminal complaint ties Bilzerian to an investigation of an explosion in a remote desert area near Vegas. The Bureau of Land Management called Las Vegas police detectives Nov. 4 after the agency discovered a field of debris from an explosion on BLM land near South Las Vegas Boulevard.
Las Vegas police spokeswoman Laura Meltzer said the investigation is ongoing and she couldn't say what evidence linked Bilzerian to the blast.