Midnight Towboy is the third episode of Season 19.
Matt Dillon guest voices as a tow truck driver in nearby Guidopolis who tows Homer's car (while he is searching for some milk for Maggie, who has become a little too clingy to Marge until Marge hires someone who persuades her into letting Maggie become independent) and ends up selling Homer a tow truck, but when Homer tows away a few too many of his friends' cars, they come up with a solution that results in Homer being put out of business...and possibly out of existence.
Marge is putting Maggie to bed, but Maggie refuses to leave Marge's arms. After Marge finaly manages to put Maggie down, Maggie leaps back into her arms and causes a jar of milk to be spilled, Marge (with difficulty) attempts to email "C.R.I.E." (Creative Responses for Infant Edu-loving), a group which enables attached children to be more independent.
Meanwhile, Homer finds out that the Kwik-E-Mart does not have any more milk, so he takes a trip past Shelbyville and Ogdenville to Guidopolis, a sleazy-looking town where everyone speaks with a New Jersey accent. He goes to the "Mook-E-Mart", and, while purchasing the milk, Homer ends up having his car towed by a man named Louie, who shows Homer the joy of towing cars for a living, and will agree to help Homer become a successful tow truck driver if, and only if, Homer would "stay off [his] turf". Homer then becomes Springfield's tow truck driver.
At home, Gerta, a C.R.I.E. counselor, arrives to help Marge with Maggie's independence. After Gerta orders Marge to leave Maggie alone in the room, Maggie's cry makes Marge desperate to hug Maggie; however, Gerta explains that "hugs are drugs, and your daughter's (Maggie) an addict". After kicking Gerta in the groin and rushing into the living room, she sees Maggie happily building her own blocks, which spells "IMOK", thus developing her independence. The next day, a more independent Maggie climbs on a table leg in the kitchen, grabs a banana, and seats herself in her highchair while eating and reading her book, much to Marge's sad disappointment that she is no longer needed.
Meanwhile, Homer becomes successful at being a tow truck driver, going even as far as to tow down Arnie Pye's helicopter. After a brief celebration at Moe's, he then tows Lenny's car, Principal Skinner's car, as well as the Sunday School bus, causing Ned to sardonically call Homer, "Towmer". However, the residents of Springfield begin to get frustrated with Homer's continuing tow-antics, so they plan a revenge upon him. Agnes Skinner, understanding how territorial tow truckers are, comes up with a plan. They place a car in Guidopolis (however, they cover the city limits sign with one saying "You're still in Springfield") next to a fire hydrant. They then spray on a "handicap parking only" sign near the car's parking spot and stuff multiple tickets under the windshield wipers, with the intention of luring Homer to Guidopolis.
At home, Maggie clips her own toenails with a pair of scissors, cuts a strand of her hair out, and places them in her very own "baby book". After seeing her more independent, Marge begins to miss her, so she bonds with a sack of potatoes, just to fill the void of losing her formerly clingy daughter, Maggie, who is now independent. At Guidopolis, Homer becomes abducted by Louie who keeps him in a trap hole in his basement with other tow truck drivers who trespassed his area, where he bonds with them.
Homer's absence causes parking pandemonium, as Lenny and Carl park in the handicap area, Agnes parks sideways, Rainier Wolfcastle parks his truck on top of her, Duffman lowered his blimp down, Horatio McCallister brings his ship on the sidewalk, and a train truck driver crashes through it all. Marge worries about Homer, who had not returned home for four days.
Maggie, worried for her father and mother's happiness, uses her new found independent abilities to save Homer by riding on Santa's Little Helper through the night to Guidopolis. On her way there, it shows how powerful the traffic is; the traffic is so bad that it becomes ridiculous, barely anyone goes out without getting in a crash, and it keeps getting worse. A humble Maggie rescues Homer from the cellar, and returns home with Homer. After giving the sack of potatoes a punch, Maggie gives Marge her pacifier, kisses and hugs Marge, reuniting with her.
Behind the Laughter
Robert Canning of IGN gave the episode 7.4/10, calling it a "solid, funny episode." He felt that "The odd scene involving the Duff blimp, the Sea Captain's pirate ship and a train engine driving through the streets was simply too ridiculous not to be funny."