He Loves to Fly and He D'ohs is the first episode of Season 19 and 401st episode overall. It first aired on September 23, 2007, and was also the first episode to air after the release of The Simpsons Movie.
Homer gets to fly in Mr. Burns's private jet and likes it so much that he decides to never fly commercial again. He tries to find a job that involves flying in a corporate jet, and hires a life coach named Colby Krause to assist him with his goal.
Whilst Mr. Burns goes shopping he finds a penny in a water fountain and reaches in to grab it; while doing so he falls in. The rushing water nearly drowns him, but Homer arrives and pulls him out of the water, saving Mr. Burns's life. To reward him, Mr. Burns offers to take Homer out to dinner. Homer says he likes Chicago deep dish pizza, so Mr. Burns takes him to Chicago on his private plane. On the plane, Homer is treated with luxury and gets serenaded by Lionel Richie.
After returning from Chicago, Homer tells Marge that he is tired of being a normal person and becomes depressed. Marge decides to help Homer and hires him a life coach named Colby Kraus, who will help with Homer's dream. Colby starts right away in his treatment with Homer by videotaping his every move. At the bowling alley and after watching Homer’s daily habits for a few days, Colby realizes that bowling is the one thing Homer is good at and enjoys doing. He instructs Homer to wear his bowling shoes everywhere he goes to help instill confidence in everything he does. The bowling shoes work, Homer becomes a new man, and as a result he receives numerous new job offers. Homer decides to only go for an interview at Handyman’s Choice Copper Tubing due to the fact that he would be required to fly in the company jet as part of his new job.
However, the Rich Texan does not hire him, but Homer decides not to tell his family and pretends to go to work every day, although he is actually just going to the local Krusty Burger. The next day, Bart's class stops at the Krusty Burger after a field trip and Bart is shocked is discover Homer sitting at a booth alone. Homer comes clean and explains to Bart that his job interview didn’t go so well when his interviewer, the Rich Texan, discovered that Homer knows nothing about copper tubing. Bart convinces Homer that he should tell Marge what has happened and Homer calls her from a pay phone. But when Homer hears Marge’s happy voice he can’t bring himself disappoint her and tell her the truth about his "new" job. Instead he concocts a story about him having to fly on the “company” jet for work and instructs Marge to meet him at the airport in an hour. Homer pays a Marine to fly him into the air, so he can tell Marge up in the air with luxury so she would not get upset. Once in the air, Marge can’t believe all the luxuries the private jet has to offer. Homer sits Marge down to tell her the truth, but just before he can, the plane endures turbulence. Homer and Marge head into the cockpit to see what the problem is, only to discover that the pilot had passed out. Homer shoves the pilot aside and takes hold of the jet’s controls. Marge pulls out her cell phone and calls Colby Kraus and frantically asks for his guidance. Thanks to Colby's motivation (him telling Homer that he heard that someone thinks he can't land the plane), Homer manages to land the plane and safely on the ground. When they land, Homer explains to Marge that flying in private jets is simply too dangerous and that he plans to go back to work at the Power Plant.
When asked to appear on the show, comedian Stephen Colbert believed that he was merely going to an audition but was "thrilled" when the production staff told him he actually had a part in the episode. Colbert was pleased that his character was named Colby and that his appearance was similar to that of his own, although he had not expected the animators to retain his glasses for the design. He based his performance on Tony Robbins and described the recording sessions as "the hardest job."
The episode averaged 9.7 million viewers and a 4.7 overnight Nielsen Rating and a 12 percent audience share. The episode had the highest demo ratings of any Simpsons episode since "The Wife Aquatic", which aired January 7, 2007. However, the ratings were down 13% from last season's premiere, "The Mook, the Chef, the Wife and Her Homer", which had a 5.3 Nielsen rating, but did better than the eighteenth season's average of 4.1. Combined with the King of the Hill episode "Suite Smells of Excess", the show finished second in the 8 PM hour, trailing NBC's Sunday Night Football, but achieving higher ratings than the second hour of ABC's Extreme Makeover: Home Edition and CBS's Power of Ten. For the overall Sunday night primetime averages, FOX finished third behind NBC and CBS, with an average 10.5 million viewers and a 4.9 rating.
Brian Tallerico of UGO gave the episode a mixed review (a C), expressing disappointment after the well received The Simpsons Movie. He felt the writers went "right back to their old clichés and sadly repetitive jokes". He did praise the altered opening sequence. Robert Canning of IGN also gave the episode 5/10, praising the opening sequence but found most of the episode mediocre, especially Stephen Colbert's appearance. Nonetheless, "even a mediocre episode will have a few comic gems hidden inside. The time spent in Chicago is quite enjoyable, including a great Ferris Bueller sight gag, and life coach Colby delivers a zinger of a line comparing Homer's attitude to that of the United States of America." Richard Keller of TV Squad praised the episode, saying "after watching so many recent ones where Homer seemed like a barely functioning mental patient, I wasn't used to a Homer that was actually fairly normal."Al Jean, the current executive producer of The Simpsons, has called the episode one of his personal favorites.
The sequence begins with Bart writing lines on the chalkboard, writing "I will not wait 20 years to make another movie". The school bell rings and he skates outside the door, showing the residents of Springfield restoring the town after the events of the movie. The multi-eyed creature from the movie is seen jumping onto Bart's shoulders, but is hit by a wrecking ball into a billboard of "Burns Construction," suggesting that Mr. Burns is attempting to regain his lost wealth by profiting from the incident. The camera then pans to a large piece of glass from the destroyed dome. Bart rides on the piece, then weaves in between characters from the movie: President Schwarzenegger, Colin, Moe Szyslak (in his "Emperor" attire and shouting "Hey!"), Russ Cargill, and the Medicine Woman, who waves her hand in a similar manner to Chief Wiggum and shouts "Why you...".
The family arrives home to 742 Evergreen Terrace, which is shown to be still under construction. Homer's car arrives with the Pig Crap silo strapped on top. The family arrive to sit on the couch, where Plopper the pig is currently sitting, with the "Spider-Pig" tune being played in the background. Homer then grabs Plopper and proclaims that the pig is his "summer love".