Josh Mankiewicz

There's J.Lo on the Grammy's red carpet. Whatever the internet was back then, she broke it. And right next to her, Sean Combs. To the world, he was the dapper hip-hop gentleman. At the same time, he was bad boy in chief with a reputation for flexing his power to get what he wanted.

There's J.Lo on the Grammy's red carpet. Whatever the internet was back then, she broke it. And right next to her, Sean Combs. To the world, he was the dapper hip-hop gentleman. At the same time, he was bad boy in chief with a reputation for flexing his power to get what he wanted.

One example. In 1999, Combs and two employees stormed into the office of Steve Stout, an executive at Interscope Records.

One example. In 1999, Combs and two employees stormed into the office of Steve Stout, an executive at Interscope Records.

Combs and his crew were accused of punching and kicking Stout, beating him with a phone and a champagne bottle. John Combs was arrested on charges of felony assault. Stout also sued him in civil court.

Combs and his crew were accused of punching and kicking Stout, beating him with a phone and a champagne bottle. John Combs was arrested on charges of felony assault. Stout also sued him in civil court.

Combs and Stout settled the lawsuit. And in the criminal case, Combs pleaded to a lesser charge. and was sentenced to one day of an anger management class. It may not have been enough. Much more serious charges were coming.

Combs and Stout settled the lawsuit. And in the criminal case, Combs pleaded to a lesser charge. and was sentenced to one day of an anger management class. It may not have been enough. Much more serious charges were coming.

A sensational criminal trial, one of the biggest in New York City. Hip-hop megastar Sean Combs facing serious prison time. Except this isn't 2025. This was more than two decades ago. It started the night after Christmas, December 1999.

A sensational criminal trial, one of the biggest in New York City. Hip-hop megastar Sean Combs facing serious prison time. Except this isn't 2025. This was more than two decades ago. It started the night after Christmas, December 1999.

Natanya Rubin was 29 then. She owned a beauty salon in New York City, and she was an aspiring singer, one who had recently given up clubbing in favor of church. Until some friends invited her to an event at a club. On her way out the door, she hesitated.

Natanya Rubin was 29 then. She owned a beauty salon in New York City, and she was an aspiring singer, one who had recently given up clubbing in favor of church. Until some friends invited her to an event at a club. On her way out the door, she hesitated.

Natanya believes that decision to swap her flats for taller heels is why she's able to be here talking with us today about what happened that night inside Club New York. What's the scene in there?

Natanya believes that decision to swap her flats for taller heels is why she's able to be here talking with us today about what happened that night inside Club New York. What's the scene in there?

Celebrities were there too, including Sean Combs and Jennifer Lopez, and Combs' protege, Jamal Shine Barrow, who had an album coming out under the Bad Boy label. Natalya says she was near the bar when she saw Combs and his entourage roll past. Someone bumped someone else. A drink spilled. Egos collided.

Celebrities were there too, including Sean Combs and Jennifer Lopez, and Combs' protege, Jamal Shine Barrow, who had an album coming out under the Bad Boy label. Natalya says she was near the bar when she saw Combs and his entourage roll past. Someone bumped someone else. A drink spilled. Egos collided.

Natanya witnessed an angry exchange between Combs and another rapper who went by Scar.

Natanya witnessed an angry exchange between Combs and another rapper who went by Scar.

Natanya says that's when Combs and his buddy Shine began backing up to the front door.

Natanya says that's when Combs and his buddy Shine began backing up to the front door.