Crazy Lucky

Remarkable Stories from Inside the World of Celebrity Icons

By: John Mason

Narrated by: John Mason

“It’s never your typical day at the office when Michael Jackson attends a meeting in person, headphones on his ears and a Walkman in his hands. Little did I know then that he was listening to the first demos for what would become Off the Wall, Thriller and Bad…”

Most lawyers aren’t like John Mason. Then again, most lawyers don’t do what he does. For decades, John Mason has been a confidante, meditator, gladiator and last line of defense for some of the most visible (and talented) artists in the world; from Brian Wilson and Roy Orbison, to Reba McEntire and the Jackson Five, to Quincy Jones, Shakira, and his dear friend of over forty years, Olivia Newton-John. In Crazy Lucky, he tells their stories from his perspective, and shows us what it means to truly have someone’s back.

A butcher’s son with humble origins, John Mason was a talented guitar player in his own right before choosing to become lawyer. Since then, he has guided his clients through devastating business bumps and craters, multi-million dollar lawsuits, divorces, child custody issues, and stalkers, while also helping to navigate breakdowns, illness, physical and mental abuse, and a wide variety of legal issues with not just hundreds of millions of dollars, but careers, on the line. Many (if not most) entertainment lawyers work through managers and agents to help celebrities achieve specific goals. Mason, on the other hand, serves as a lynchpin to his clients’ inner circle, a steady presence in what is often a privileged, but harrowing lifestyle.

Crazy Lucky is a career retrospective packed with never before heard stories. A rollicking journey for anyone interested in entertainment history, Crazy Lucky shows what it takes to represent the interests of some of the biggest names in the world, in critical, career-defining moments.

©2025 John Mason (P)2025 John Mason

Amazingly true stories of how the industry was shaped. Never met any one like him and likely never will.

John is such a down to earth lawyer beyond compare. His empathy for his clients stands out so supremely as the his most important mission. In a world of narcissistic celebrities, John always comes back to the core values that bond us as humans. The world of music has been lucky to have this cool hand and honest arbiter. And I’m lucky to have called him friend for twenty five years

John Mason had a charmed career and wrote a wonderful book . Thank you

Listening to John’s voice tell his own story was heartfelt. I felt like I was in the rooms

Solid and Insightful

For decades, John Mason has been a towering figure in entertainment law. Despite the book’s title he is neither crazy nor lucky but a brilliant legal mind and highly skilled negotiator with a fierce desire to protect his clients and those he loves. “Crazy Lucky” is a must read for anyone interested in learning the insides of a unique industry during transformative and turbulent times.