In Honour of The Late Show’s 20th Anniversary — One of David Letterman’s Oddest Moments

When Johnny Carson, signed off from The Tonight Show for the final time in May, 1992, it marked a seismic shift in the late night landscape. The king was retiring, and the rumoured heir to the throne – David Letterman – got unceremoniously bumped from the gig in favour of Jay Leno. Letterman, as a result, took his act to CBS, debuting The Late Show with David Letterman a year later, on August 30, 1993.

Today, twenty years later, Dave celebrates a landmark anniversary. To commemorate the occasion, we wanted to post one of Dave’s oddest, most outrageous moments. While there’s been many – from Madonna’s potty mouth to Crispin Glover throwing a kick at the host’s head to stupid pet tricks to Dave confessing on air to an affair that morphed into a blackmail plot – one guest constantly provided fodder for Letterman while truly proving to be a bit of an “oddity” in his own right: Richard Simmons.

The above clip is one of the exercise guru’s most memorable appearances on Dave’s show. Let’s just say that he’s sweating, but it’s not to the oldies.