14. Hugh Hefner
Hugh Hefner, legendary “Playboy” founder, not only brought the magazine to global heights but also reveled in luxury with opulent parties alongside Playboy Playmates. While boasting magazine earnings of up to $45 million, he led a lavish lifestyle, culminating in a modest $1 million annual salary and almost free residence in the iconic Playboy Mansion after selling his empire.
Despite selling Playboy for millions, Hefner’s wealth was surprisingly modest at his death at 91. Living in the Playboy Mansion for a symbolic rent, his fortune from 2009 divorce filings revealed $43 million, contradicting the opulent lifestyle funded by significant monthly expenses, hinting at a financial discrepancy between perceived wealth and actual assets.