7. David Letterman and Regis Philbin

Complex Says: When Regis Philbin retired, David Letterman presented him with this lovely red Vespa as a gift. Unfortunately, Philbin had no idea how to ride it, and promptly crashed it on the Late Show with David Letterman set. Luckily, the talk show host suffered no serious injuries--other than possibly to his dignity. Also, either Letterman is really tall, or Philbin is really short.