Flashback: David Letterman on Our July 1997 Cover

Be sure to see what celebrities and comedians (not mutually exclusive categories, per se) are saying on Twitter about David Letterman’s impending departure in 2015. In the meantime, we present in homage the July 1997 cover of Indianapolis Monthly here says a lot.

As you can see, his signature gap-toothed look hasn’t wandered over the years.

And from the “Did You Know?” files, this:

Jeff Smulyan, CEO of Emmis Communications, IM‘s parent company, was actually Letterman’s second boss after the youngster graduated from Ball State University in 1969. “He was the midday guy,” Smulyan says of overseeing Letterman’s early work at WNTS-AM in Indianapolis, where Smulyan was general manager at the time. Previously, Letterman worked at local television station WLWI, which became WTHR-TV.

“When he took the job, he said ‘I’m gonna try to make it in Hollywood,'” says Smulyan. “The guy who replaced him was Rick Cummings, the first employee here at Emmis. David also bought shares in Emmis and was on the board for a while before it went public. We don’t see each other often anymore, but I always thought he was the most brilliant, funniest human being who ever lived. I just think he’s incredible.”

Inset photo: July 1988 cover of IM featuring Jeff Smulyan