Team: Rahal Letterman Racing
Years of Ownership: 1996-present
Championships Won and Playoff Appearances: 2004 Indy 500 Winner

Everyone knows that racing is cool, including one of the kings of late-night talk show television, David Letterman. The CBS funny man hit the throttle in 1996 when he took a minority stake in Team Rahal Racing. In 2002, the team saluted Letterman by entering the Indy 500 as Rahal Letterman Racing and two years later the name became permanent. The very next race after the change, they won the Indy 500. Boom.