David Letterman on ‘The Tonight Show,’ c. 1978

As everyone knows, David Letterman is retiring. On May 20th, after 33 years on late night TV, Dave will host his the final Late Show with David Letterman on CBS. When its previous incarnation, Late Night with David Letterman, debuted on February 1st, 1982, on NBC, it may have seemed to some viewers that he appeared out of thin air, but Dave had already worked a number of jobs in the entertainment industry, including stints as a TV weatherman; a joke writer for Good Times star Jimmie “J.J.” (“Dyn-O-Mite!”) Walker; and as a cast member on Mary Tyler Moore’s short-lived comedy-variety series, Mary. After several high profile appearances on The Tonight Show, NBC gave him his own morning talk show in 1980. Though The David Letterman Show crashed and burned that same year, the network gave Dave another chance, and, thus, Late Night was born.
 

Looking sharp on ‘Mork & Mindy’,1979

Letterman also appeared on a few game shows in the 1970s, including one called The Riddlers, which he hosted. In 1977, a pilot episode was produced, but the networks passed on it, so the show went unaired. The pilot did eventually see the light of day, though, when it appeared on the Game Show Network’s Halloween special in 2000.
 

 
The celebrity panelists assembled for The Riddlers all made the rounds back in the day and will be recognizable to anyone who digs ‘70s game shows (including Michael McKean, then known as one-half of Lenny & Squiggy from Laverne & Shirley). On this episode of The Riddlers (they’re all pretending like it’s not the first), the familiar are facing off against a group of unknown dance instructors…Huh? Don’t ask me. I can tell you that the show revolves around riddles (duh), which alternate between clever and Match Game-style bawdiness.

As for Letterman, this is the Dave we would come to know and love—repeatedly insulting the panelists, and biting the hand that feeds (right out of the gate, he makes fun of the game show format), inducing quite a few laugh-out-loud laughs with his now-patented dry wit and heavy-on-the-sarcastic tone. The celebs ain’t half-bad either (unsurprisingly, McKean is the funniest), and neither is The Riddlers, but it’s just as well it didn’t get picked up. Dave just might have become the next Wink Martindale, and the world would have been deprived of “Stupid Pet Tricks” and Larry “Bud” Melman. I shudder to think.

For our purposes, there’s no need to explain the rules of The Riddlers, so if you really want an outline before you watch the thing, go here. Otherwise, follow along at home and enjoy this rarely seen side trip on David Letterman’s road to a career in what he has mockingly called “show bidness.”

 
Be sure to check out WFMU’s excellent—and thorough—2010 blog post on Dave’s pre-Late Night years.