4. Sean Combs
Sean Combs (aka P. Diddy, aka Puffy, aka Puff Daddy, aka Puff) has made billions from Ciroc, his brand of vodka. He’s also been pretty successful as a producer and rapper, and has worked with groups like Danity Kane, along with veteran artists like Mary J. Blige. Combs has even rapped about how much money he has in a variety of songs. So, why would he have such a hard time tipping waiters appropriately? Apparently, Combs was out with 14 of his friends, and racked up a pretty huge tab. However, he only left a $40 tip. That’s far from a decent tip for a person who can practically make millions in his sleep.