John Legend ,  Net worth: $45 Million – Boeing 757,  Estimated $28 Million

The Legend Experience was a dream come true for a handful of John Legend fans in 2015 who were able to join the star and climb aboard the private Boeing 757 for a tour around the U.S. and Europe. While a once in a lifetime opportunity, this was no charity event. Fans had to dig deep into their pockets to be able to afford the trip. This  Boeing 757 price today is about $ 100 million for a brand New jet. For some, however, the experience was a priceless opportunity, so cost was not an issue. On Valentine’s Day,  Legend and his wife, Chrissy Teigen, took the private jet again for a quick Valentine’s Day dinner in a French restaurant.