Homer gets a life coach (voiced by Stephen Colbert) after realizing that he wants to be rich and successful enough to buy his own private jet.
- Brick Joke: At the beginning of the episode, it's revealed that Mr. Burns ate a mini-cellphone because he mistook it for a lemon drop. A later scene has the phone ringing from inside him and Smithers shoving a stick through his throat to answer the call.
- Continuity Nod: The couch gag shows that Springfield is still rebuilding from the events of The Simpsons Movie.
- Don't Tell Mama: Homer doesn't want Marge to know he failed to get the new job.
- Pun-Based Title: The episode's title is based on a slogan Delta Airlines used from 1987 to 1992: "We Love to Fly and It Shows".
- Sensual Slav: There's a beautiful flight attendant in Mr. Burns' airplane. She's a tall and slim blonde and her name's Svetlana, a decidedly Slavic name. She's supposed to do anything for Homer. Anything except sex. And Mr. Burns does mean anything.Homer: Oh... I'm aroused and confused.
- Sequel Snark: In reference to The Simpsons Movie, the episode's chalkboard gag has Bart writing, "I will not wait 20 years to make another movie."
- Song Parody: Homer requests Lionel Ritchie alter his song "Say You, Say Me" to "Hey You, Beer Me". Then he wants all the words to be "beer".Homer/Lionel: Beer beer, beer beer.
- Take That!: According to a play that Homer and Mr. Burns watch in Chicago, Starbucks charges a billion dollars for a cup of coffee.
- Too Dumb to Live: After landing a plane, Homer decides to drive it to a proper place and ends up sending it to the sea.