Price: $30.38 million
Out of its original planned production line of 25, only 10 of these Spiders were ever made due to lack of demand. But a man named Eddie Smith thought it was one of the coolest cars in the world.
In 1968 he purchased a 275GTB NART Spider for between $8,000 and $14,500 ($59,000-$107,000 in 2019) and refused to sell it, even to Steve McQueen after the actor crashed his own NART Spider according to Car and Driver.
Eddie Smith passed away in 2007, leaving the car to his son, Eddie Jr. He put it up for auction in 2013, where it fetched $25 million at auction ($27.5 million with fees). He gave the proceeds away to charity.