Emmis Communications

As you can see, his signature gap-toothed look hasn’t wandered over the years. Trivia: Jeff Smulyan, CEO of Emmis Communications, IM’s parent company, was Letterman’s second boss after the future star graduated from Ball State University.

“Indiana has traditionally had a friendly business environment that is the backbone of the Hoosier economy,” says CEO Jeff Smulyan. “This is two steps backward and runs counter to what businesses are demanding.”