In 1992 Southern California Amateur Radio operators uplinked a video of  stand-up comedian Jay Leno, host of NBC’s The Tonight Show, to the Space Shuttle Columbia through Jim Steffen, KC6A’s station in Long Beach, California.

Watch Jay Leno – SAREX Shuttle Amateur Radio Experiment 1992

Past SAREX Missions
http://www.arrl.org/files/file/ARISS/ARRLWeb_%2520Past%2520SAREX%2520Missions.pdf