Before Jon Stewart became the liberal lion of late-night satirical news who tore through bow-tie clad CNN hosts with rhetorical ease, he cut his teeth as host of MTV’s The Jon Stewart Show, which ran for less than two years on the network. For the final episode, which aired on June 23, 1995, Stewart invited late night legend David Letterman, who had hosted the 67th Academy Awards just months before. (Forrest Gump won best picture, in case you were wondering.)
After the The Jon Stewart Show ended, Letterman actually signed Stewart to a contract with his Worldwide Pants company. Stewart would go on to serve as a guest host for Tom Snyder, and start his own show called Where’s Elvis This Week?, before taking over for Craig Kilborn as host of Comedy Central’s The Daily Show in 1999. And the rest, as they say, is history.
Watch Letterman’s appearance on the final episode of The Jon Stewart Show below. And to prep, consider this time stamp: the late night legend, who retired last week, came out to Live’s “All Over You.”
Previous: 10 Memorable ‘Letterman’ Appearances