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Via @realjohngreen, “Very sad to hear of the death of Maya Angelou. She was a brilliant writer who used her platform with care and thoughtfulness. Godspeed.”

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.

More than 100 judges from the likes of Esquire, Bon Appetit, and Vanity Fair narrowed the field of finalists, including these from IM’s 2013 issues.