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"He Loves to Fly and He D'ohs" is the first episode of season 19. It originally aired on September 23, 2007 and was written by Joel H. Cohen and directed by Mark Kirkland. Stephen Colbert and Lionel Richie guest star. It was the first episode to air after The Simpsons Movie.

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 to help fulfill this dream...