These days, Diddy is a multi-hyphenate rap mogul, with a record label, fashion label, television network and alcohol business to his name.
But he's revealed that one of the "greatest" times of his life was a summer spent living in an Amish community in Lancaster, Pennsylvania.
During the two-month stay, he picked berries and learned to milk cows.
"It's one of the things that helped to make me who I am," he told US chat show host Jimmy Kimmel.
The Amish community in the US is renowned for shunning modern technology and preserving traditional ways of life.
They dress simply and live without phones or electricity, using horses for farming and for transport.
"It's a chance to really kind of get away and just - no electronics," explained Diddy. "It really teaches you how to just relate with each other."
The star, whose real name is Sean Combs, was brought up in New York. He ended up in Pennsylvania after his mother Janice contacted The Fresh Air Fund, a non-profit agency that provides free holidays to children from low-income communities.
Reminiscing about the traditions that he became involved in, the star said: "I had to milk cows, I'd pick berries. It was a lot of chores. They wake up and they do their chores.
"I remember we used to go to church and at the church, they used to just have these lavish meals. And it really kind of taught you family. I rode around in a horse and buggy everywhere".
"And now you've got a Bentley," joked Kimmel.
In fact, Combs is the second wealthiest artist in hip-hop, according to Forbes magazine, which estimates he's worth $825 million (£636 million).
In addition to his own hits, including I'll Be Missing You and Been Around The World, the star's Bad Boy record label has sold more than 500 million albums worldwide; and he's currently one of the judges on US talent show The Four.
But Combs said his Amish hosts were probably unaware of his success.
"I had no way to stay in touch with them," he said, adding: "I think about them all the time. And I'm just like, man, I wonder if they know, you know, what I grew up to be. But I don't think they did."
The 48-year-old said he'd still like to make contact with the family, telling Kimmel: "It would be great."