Will Smith | Bentley Azure | $370,000

Will Smith started rapping at the early age of 12. He idolized staples such as Grandmaster Flash but dashed his rhymes with a pinch of comedy that would eventually become his trademark. Years later, Smith transitioned into acting; in The Fresh Prince of Bel-Air, Smith played on his rapper persona. He also deserves credit for appearing in Men in Black, where he fought aliens. His success in music and film has allowed him to focus on investments, and the most notable is his Bentley Azure, the most expensive car in Will Smith’s collection.

This gem is an ultra-exclusive convertible powered by a turbocharged V-8 providing 50 horsepower. However, due to the fast-changing times, this beauty has somehow lost its allure. For men of refined taste like Smith, driving this beast from a bygone era is a privilege most people don’t have.