After a trip to Chicago with Mr. Burns on a private jet, Homer wants more than that and gets a life coach (voiced by Stephen Colbert).
Tropes:
- Animated Actor: The main guy that Homer and Burns see at The Second City? That's Dan Castellaneta playing himself! (He started off there.)
- Borrowed Catchphrase: in the scene Homer slaps Bart 3 times, he (Bart) uses Homer's "D'oh" in response to each slap.
- 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:
- The mutated, multi-eyed squirrel almost attacks Bart before a wrecking ball knocks it away.
- Bart does a skateboard trick off of a piece of the shattered glass dome, referencing the climax of the movie, in which Homer drives a motorcycle across the dome.
- The silo full of pig poop is shown strapped to the car still, and Homer still has his pet pig.
- Don't Tell Mama: Homer doesn't want Marge to know he failed to get the new job.
- Dope Slap: Homer returns Bart's snark with a couple of these.
- Improv Comedy Is Inane: Homer and Mr. Burns fly to Chicago together, where they catch an improv show at the famous Second City Theater and feed the performers the premise of "a drunken billionaire at a Starbucks in Siberia." The ensuing scene plays out in two lines.
- Male Performer: [Acting drunk] Uh, excuse me, I need a (Hic) I need a coffee. Can you change a billion-dollar bill?Female Performer: Our coffee COSTS a billion dollars. This is Starbucks... in Siberia!
- 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.
- Special Edition Title: The usual opening credits sequence is replaced by a one-off version showing Springfield still in ruins after the events of the movie, with many of the one-off characters from the movie making cameo appearances.
- Rule of Three: Homer gives Bart 3 consecutive Dope Slaps
- Take That!: To both Starbucks and hacky jokes about their coffee prices. According to the improv performance 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.
