Will Smith talks about ‘lying on the floor in a jail cell’ when he hit ‘rock bottom’

Move over Jada Pinkett Smith, it’s Will Smiths’ turn to get it all out. The artist sat down with the one and only Oprah Winfrey for Apple TV+’s The Oprah Conversation: Will Smith, airing today. And in a clip from the show shared with Entertainment Tonight, it’s clear Will didn’t hold back, as he discussed losing everything right before Fresh Prince of Bel-Air. In addition to the government seizing his cars and home, he ended up in jail, what he describes as “rock bottom.” He also opened up about how he feels like he has failed “every woman” he has ever been with.

© Will Smith

Will met with Winfrey ahead of his memoir, Will, which will be released on Nov. 9. During the intimate conversation, she told him, “I realized…you basically lost everything,“ “The government seized your cars, it took your home, you ended up in jail. You describe it in two words actually, ‘rock bottom.’ What was at the root of that downfall, Will?”

“When it rains, it pours. So getting into the fight at the radio station, Charlie punching the dude that landed me in jail, so the money is gone, the car is gone. I am laying on the floor in a jail cell and I am like, ‘You’ve got to be kidding me!” Will replied. “I won a GRAMMY eight months ago. Like, what is happening?“ he recalls. ”And it‘s just the spiral when it starts going the other way. It’s like, sometimes you just have to get out the way and wait until the downward spiral stops.“

The Pursuit of Happiness star also admitted to his belief of “failing every woman I interact with.” “I want to tell the truth. I want to let people have it. I‘ve carried, most of life, the sense of failing every woman I interact with. I haven’t talked about that publicly,” he said.

Will shared two pictures yesterday on Instagram ahead of the episode. “How it started / How it’s going” he captioned the pic.

Winfrey took to Twitter to share her excitement for the conversation and praised Will‘s book. “ His new memoir is inspiring, fun, and fantastic. #WillTheBook is EVERYTHING. It was a real joy for me to talk to him about his words, his new movie @KingRichardFilm, his life, and so much more,” she wrote with a picture of them posing together.

The Oprah Conversation: Will Smith will premiere on Apple TV+ on Friday, Nov. 5.