P. Diddy – Rolls-Royce Phantom Drophead Coupe, Estimated $440K

Now an established business going by his real name Sean Combs, this person became well-known under his performing name P. Diddy. Worth $855M in 2019, Diddy is among the wealthiest rap moguls in the entertainment business. He’s a heavy investor and has, among other luxury items, a collection of expensive rides. This includes a ’58 model Corvette, a Lamborghini Gallardo Spyder, and a Maybach 57. They also include a Rolls-Royce Phantom Drophead Coup which cost $533K at the time Diddy bought it in 2015 and was the most expensive Rolls-Royce. Flaunting his opulent way of living, Diddy held a wildly over-the-top New Year’s Eve party in Miami in 2018.