The Simpsons (1989): Season 19, Episode 1

19 - 1: He Loves to Fly and He D'ohs

After Homer saves Mr. Burns from drowning in a mall fountain, Burns thanks him by taking him on a whirlwind trip to Chicago on his private plane. Homer is smitten with the luxury jet and all the perks that come with it, including flying with song legend Lionel Richie, who serenades him with a customized version of "Say You, Say Me." After returning home, Homer makes it his mission to find a job that offers him the chance to fly on a corporate jet and enlists a life coach, guest star Stephen Colbert, to help fulfill this dream.