Midnight Towboy is the third episode of season 19. It originally aired on October 7, 2007. It guest stars Matt Dillon.
Homer gets a job as a tow truck driver, but when he starts towing almost every car in Springfield, his friends try to make Louie, his boss, trap Homer towing a car in Louie's territory.
The episode begins with Marge putting Maggie to bed, however Maggie refuses to leave Marge's arms. After Maggie's attachment towards Marge causes a jar of milk to be spilled, Marge (with difficulty) attempts to email "C.R.I.E" (Creative Responses for Independent Edu-loving), a group which enables attached children to be more independent.
Meanwhile, Homer finds out 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 purchases milk and ends up having his car towed by a man named Louie. Louie 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, a woman dressed in attire similar to those of a hippie arrives to help Marge with Maggie's independence. After the woman orders Marge to leave Maggie alone in the room, Maggie's cry makes Marge desperate to hug Maggie; however the woman explains that "hugs are drugs, and (Maggie) is addicted". After rushing to the living room, she finds Maggie is happily building her own blocks, which spells "IMOK". Later, a more independent Maggie climbs on a table leg in the kitchen, picks up a book and banana and seats herself in her high-chair, much to Marge's sad disappointment that she's no longer needed.
Homer then becomes a successful tow truck driver, going even as far as to tow down Arnie Pie'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". The residents of Springfield begin getting frustrated with Homer's continuing tow-antics, so they plan a revenge upon him. They put a car in Guidopolis (however, they cover the city limits sign with one saying "You're still in Springfield") beside a fire hydrant. They then spray on a handicap parking only logo 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, clips a wad of her hair out, and makes 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. Lenny and Carl park in the handicap area, Agnes Skinner parks sideways, Rainier Wolfcastle parks his truck on top of her, Duffman lowered his blimp down, the Sea Captain 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 their, we see how powerful the traffic is; the traffic is so bad that it's 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 and hugs Marge, reuniting with her.
The episode had 7.8 million viewers in its original broadcast. 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."