Raise your glasses, because hip-hop’s biggest mogul, Diddy, is turning 42!

It’s difficult to find the words to describe the extraordinary level of achievement that businessman Diddy has garnered over the span of his career. On top of his well-known label, Bad Boy Entertainment, showcasing many of the hottest artists over the past two decades, Diddy’s brand has expanded to include his clothing line, Sean Jean, fragrance lines for men and women, and his premium vodka, Ciroc.

PHOTOS: Celebs who Give Back

Ever the giver, Diddy recently contributed a substantial amount to the Boys & Girls Club of Harlem to help save the organization from closing. He also recently launched his new line of Sean Jean at Macy’s in New York City. 

PHOTOS: Hip Hop Heartthrobs

He has won three Grammys, released six albums, and has transformed his name countless times — from Puff Daddy to Sean Combs to P. Diddy. At 42, the mogul is estimated to be worth $500 million and is the closest to becoming the first Hip-Hop billionaire.

The rapper is also a family man, and prides himself in being a father to his five children, and stepfather to one.

Happy Birthday, Diddy!