But a Bieber tattoo? That was unexpected, Berry said.
"My reaction was 'whoa, crazy, crazy,'" Berry said, uttering one of his familiar catchphrases. "It was unreal, some of the stories."
There are uplifting tales too, like the cliff diver who was temporarily paralyzed and managed to still draft his fantasy football team from his hospital bed one week later. He's since regained the ability to walk and credited fantasy sports in aiding with his recovery.
"There is no excuse to missing draft day," Berry said. "If a guy can draft a week after he's paralyzed, I think anyone can find a way."
The book is full of stories but not the fantasy sports advice Berry is known for. After a stint as a Hollywood writer, where Berry penned several "Married With Children" episodes, Berry gave up the career to focus on fantasy sports writing full-time.
He catered to readers at his own site, sprinkling stories about his personal life into columns. Berry's willingness to talk openly about his personal likes and dislikes got the attention of fantasy sports fans who were looking to be entertained just as much as they were trying to figure out who to start in any given week.
Berry's first-person style is modeled after radio host Howard Stern's. Berry is a longtime listener.
Berry considers himself a regular guy. He likes superhero movies, football, Bruce Springsteen music and Las Vegas.
"If I think it's interesting, then I think other people will find it interesting," Berry said.
ESPN bought his fantasy sports website six years ago. He's now a staple on the cable sports brand. He appears on TV programming, he co-hosts a podcast and he writes a weekly column, often with stories about his personal life.
When fans see Berry in public, they thank him for stories about his wife, his twin daughters and his parents. His mother Nancy is the mayor of College Station, Texas.
"It's never, 'hey, thanks for having Arian Foster in his breakout year. I got him in the fifth round, thanks to you,'" Berry said.
So when Berry was approached about writing a book, he decided to eschew traditional fantasy advice. Instead, he discussed the crazy lengths fantasy owners will go to win in between tales about his life.
There's a story about a Red Robin restaurant employee who participated in his football draft while at work. He wore the Red Robin mascot costume and drafted with a cheat sheet taped to the bill.
There's a story about an Army serviceman who managed to draft while his Afghanistan base was being bombed. Berry was skeptical, until he was forwarded an Associated Press story that indicated the bombing took place at the time of the ESPN live fantasy football draft.