49. Playboy

Model: Big Bunny
Cost: $12 million*
Net Worth: $500 million* (Valuation)
If you’ve been following the Playboy news headlines recently, then you know that the media company has recently recreated its famous “Big Bunny” jet. Hugh Hefner’s estate sold off the old Big Bunny to the Slater Family, and they recreated the black-and-white Playboy plane using the former DC 9-30 jet as a model.

The original Big Bunny was a sight to see in the skies in the ‘70s, and people with Playboy nostalgia are glad that this vintage plane is going to be flying once again. Hefner’s estate has struggled with mounting debts, so this could be a sign that the company’s financial tides are turning.