He made a demo tape, and after being turned away from every label, he formed his own, Roc-A-Fella records. He released his first album in 1996 and went on to produce an unrivaled string of multiplatinum hits, making hip-hop history.
In his personal life, he's been involved for three years with superstar Beyoncé. He doesn't discuss their relationship but told Walters that she's a "great person."
And when asked if he thought Beyoncé was "bootylicious," he said "yeah, yeah, yeah."
The secret to his success? Jay-Z says it's "truth."
"That transcends race, age, anything. People understand truth ... and you can see that in my music."
Generally, the list of most-fascinating people excludes those who have died, but this year an exception was made for the "Crocodile Hunter," through his remarkable and fascinating widow, Terri Irwin.
When Terri visited Australia in 1991, fate stepped in. She described the moment when she first saw Steve Irwin in a reptile park, catching a crocodile, as "amazing."
"I fell then and there … love at first sight. I thought then, 'Oh, this guy, this is the one for me. He's amazing.'"
It was instant animal attraction, and within the year, they were married. For their honeymoon, naturally, they went on a crocodile expedition, inviting a camera crew along. That honeymoon became the first episode of Animal Planet's "The Crocodile Hunter."
Work, life and love intertwined seamlessly. They had two children: Bindi, now 8, and Bob, now 3, and included them in the show. Steve's family's zoo grew to be a major conservation center, and a second home for the children. On screen and off, Steve seemed invincible.
Barbara Walters asked Irwin if she ever worried about her husband's dangerous work.
"Neither of us ever worried about the wildlife," Terri Irwin said. "I worried about any time we were apart. We felt, if we were together, we would be OK."
This September, Terri and Steve weren't together. She was traveling with the children and he was filming off the Great Barrier Reef, when a sting ray's barb pierced his heart. Steve Irwin was killed at the age of 44. Shocked fans watched his memorial service, which was broadcast around the world.
Terri Irwin told Walters that she had lost her prince.
"You know what I'll miss the most -- and it's very selfish -- he was fun. Steve was fun. He taught me that it's OK to play ... in the rain," she said, choking up. "And splash in my puddle. And let the kids … get dirty. He didn't sweat the little stuff. He saw the big picture. And he had fun! Now I'm going to work really hard at having fun again."
She could have made the list most any year, but this year was tailormade for her, since she was reputedly the inspiration for the hit film "The Devil Wears Prada."
In the world of fashion, everything changes, except for Anna Wintour and her power. For two decades, the 57-year-old Wintour has reigned over the Vogue magazine empire. But when it comes to fashion, Wintour told Walters that style doesn't necessarily mean couture:
"Jeans and T-shirts can be equally fashionable as an Oscar de la Renta ball gown," she said.
Wintour was born in London, her father the editor of a major newspaper. When she was 25 years old, she arrived in America, eventually landing the top job at Vogue.