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.

Feeling that Maggie is getting too clingy, Marge hires a counselor to teach her the "C.R.I.E. Method," a counseling program that helps parents raise their children to be very independent at an early age. But the method works a little too well, leaving Maggie with no need for Marge at all. Meanwhile, Homer goes in search of milk for Maggie in Mookington and ends up having his car towed by a tow truck driver named Louie (Matt Dillon) who introduces Homer to the joy of towing cars for a living. Louie invites Homer to be the tow truck driver for Springfield on one condition: that Homer stay off of Louie's turf in Mookington. When Homer gets a little too "tow happy," the residents of Springfield set Homer up to look like he's towing in Louie's territory, and Homer must suffer the wrath. With Homer missing, the newly independent Maggie is spurred to action.