Number 8: Brough Superior
One of the first bikes that Jay Leno bought to start his collection was 1939 Brough Superior. He acquired this one in the 80s and paid $5,000 for it. Back then it was a lot of money, but Leno was aware of its potential, and this bike now has estimated worth of about $500,000. Even back in the day, this motorcycle could go over 100mph mark.