The music and liquor mogul was once again at the top of Forbes' list, worth an estimated $700 million, an increase of $120 million from the previous ranking, mostly driven by his new multi-platform channel Revolt TV.
The list's major element of surprise was who followed Diddy: Dr. Dre. He edged out Jay Z, who has been a stationary number two on Forbes' list since its beginning in 2011.
"I don’t think it says anything negative about Jay Z," Forbes senior editor Zack O'Malley Greenburg tells ABCNews.com. "It just says something positive about Dr. Dre and what he’s been able to do with his headphone company."
That headphone company is of course Beats by Dr. Dre, which he co-founded in 2008 with Jimmy Iovine, Interscope chief.
Here's more about the success of Diddy, Dr. Dre and the others on the list.
1. Sean "Diddy" Combs category: $700 million
Sean Combs, 44, has made a large chunk of his estimated $700 million net worth through the "successful" launch of Revolt TV, of which he is a majority owner, Greenburg said. He adds, Revolt TV is "Diddy's answer to MTV."
"He wants to create an MTV for the next generation," with content that translates smoothly on cable, iPad, and other devices, Greenburg said.
Despite success in business, Combs isn't hanging up his music hat yet. He just debuted a single "Big Homie" two weeks ago, using his stage name Puff Daddy.
2. Andre "Dr. Dre" Young category: $550 million
Andre "Dr. Dre" Young, 49, is a producer and rapper whose most recent successes relate to his headphone company. Beats by Dr. Dre is only around five years old, but the company's annual sales reportedly exceed $1 billion and covers two-thirds of the headphone market, Forbes reports.
"He transformed something that plays audio into a fashion accessory," Greenburg said. The recent addition in January of subscription service Beats Music and, before that, Beats Pill wireless speakers have contributed to the company's transformation into a lifestyle brand, Greenburg adds.
Read More: Dr. Dre and Beats Music: Genius or Copycat?
3. Jay Z category: $520 million
The estimated $520 million net worth of Shawn "Jay Z" Carter, 44, (a.k.a. Mr. Beyonce Knowles) came from the $204 million sale of his clothing brand Rocawear back in 2007 and the $150 million deal with Live Nation in 2008, Forbes reported.
Greenburg said Jay Z is the most successful recording artist out of the people in Forbes' list.
"That enables him to tour a lot and make a ton of money on the road," Greenburg said.
4. Bryan "Birdman" Williams category: $160 million
Bryan "Birdman" Williams, 45, would have a higher net worth if he wasn't splitting his fortune with his brother, Ronald "Slim" Williams, after the two co-founded Cash Money Records two decades ago, Forbes reports.
The record label represents a slew of hip hop and R&B artists including Nicki Minaj, Drake, Bow Wow, Lil Wayne, Jay Sean, Busta Rhymes and Paris Hilton.
5. Curtis "50 Cent" Jackson III