Homer Simpson, Grampa Simpson, Barney Gumble, Krusty the Clown, Groundskeeper Willie, and others
Marge Simpson, Patty Bouvier, and Selma Bouvier
Bart Simpson, Nelson Muntz, Ralph Wiggum, Todd Flanders, and others
Apu Nahasapeemapetilon, Moe Szyslak, Chief Wiggum, Comic Book Guy, Lou, and others
Mr. Burns, Ned Flanders, Principal Skinner, Waylon Smithers, Kent Brockman, and others
Milhouse Van Houten, Rod Flanders, Jimbo Jones, and others
Agnes Skinner, Brandine Del Roy, Dolph and others
Music From This Episode
"My Kind of Town" by Frank Sinatra (Used during the Chicago montage with Homer and Mr. Burns.)
"Clair de Lune" by Claude Debussy (Used several times throughout the episode during Homer's times of depression and loneliness.)
The Wrigley Field sign in Chicago says on the bottom line, "The 1908 World Champions", which is the last time the Cubs won the World Series. The real sign has an electronic display at the bottom.
Stores in the Springfield Mall: Restoration Software, Designer S'mores, Jewelry, Crazy E.T.'s Phone Home, The Shoe-Inn, Box Barn, Ah, Fudge!, Cost-Mo.
The Burns Construction sign during the intro reads: "Building Cheaply Charging Dearly." On the sign is a picture of Mr. Burns holding money bags.
During the montage in Chicago, Mr. Burns sports a Chicago Cubs baseball cap and Homer wears Brian Urlacher's #54 Chicago Bears jersey.
Mr. Burns' shopping list:
Laudanum (Crossed off)
Cotton gin (Crossed off)
Spats (Crossed off)
On the bulletin board at the power plant Homer staples up a sign with a sandwich on it reading: "Lost Sandwich Description: Delicious."
Places spotted as Mr. Burns and Homer enjoy a night on the town in Chicago: Ditka's, Wrigley Field, Wherever the White Sox Play, First Bank of Oprah, Ferris Bueller's Day of Beauty, and Second City Theater. A sign on the facade of Second City Theater reads: "See great comedians before they get fat."
Homer reveals that he has a 217 bowling average.
iPhones are on sale for 20 cents at the Springfield Mall.
Homer's favorite pizza is Chicago deep dish.
The year on the penny Mr. Burns leans into the fountain after is 1989, the same year The Simpsons made its series debut.
Homer: One small coffee, please. And a bunch of those placemats with the mazes on them.
Pimple-Faced Kid: They're all the same maze.
Homer: Somebody's gotta do 'em.
Mr. Burns: Why do I need another penny? I have billions. Still, if I don't take it, that hoodlum over there might.
(Mr. Burns takes Homer out for dinner.)
Mr. Burns: So, Simpson, I hear you like pizza pie.
Homer: I do! My favorite is Chicago deep-dish.
Mr. Burns: Chicago, eh? Well, what if I took us there now?
Homer: Drive to Chicago? I don't have time for that. I have to be back at work by Monday and my boss is a total jerk.
Homer: Oh, what's the point of putting my socks on? I'd just have to take them off again a week later.
(Homer calls Colby Krause to help coach him through a situation.)
Colby Krause: All right Homer what is it you're attempting to do? Win over a difficult client?
Homer: I'm trying to land a plane with no experience!
Colby Krause: Homer, I gotta tell you I'm not very good. I went to the Harvard of the South.
Homer: Duke? That's good!
Colby Krause: Not Duke.
Colby Krause: A little further south. Don't make me say it.
(Bart catches Homer at Krusty Burger instead of his "new" job.)
Homer: I couldn't bear to tell your mother, so I hang out here all day.
Bart: But, Dad, you gotta tell her. She's been buying brand-name groceries.
Homer: Brands like "Miser's Choice" and "Day-Old Delights"?
Bart: No, things rich people buy, like Campbell's soup and Pepsodent.
Marge: Homer, you smell like Chicago. Did you fly there in a commercial airline?
Homer: No way. Commercial is for losers and terrorists. I flew in a private plane.
Marge: Wow, is it much different from normal plane?
Homer: Please, tell me you're joking. It's the difference between champagne and carbonated pee.
(Homer meets Mr. Burns' flight attendant.)
Svetlana: My name is Svetlana, but you can call me "Hey, baby."
Mr. Burns: And just so you know, she'll do anything for you. Anything except sex. And I do mean anything.
Homer: (Drooling) Ohh, I'm aroused... and confused.
Colby Krause: Homer, here in the bowling alley, you're a totally different man. Relaxed, confident...
Homer: Is this going somewhere?
Colby Krause: What we have to do is figure a way to make "Bowling Alley Homer" into "Everyday Homer."
Lenny: I have an aunt who became an uncle. Is it like that?
(Awkward silence. Lenny wanders off.)
Colby Krause: I want you to wear those bowling shoes out the door and everywhere you go. It's crazy, but it just might work!
Homer: Dr. Frederick J. Waxman, you're a genius!
Colby Krause: That's not my name.
Homer: I wasn't talking to you.
(Homer takes the control of the jet.)
Marge: Homie, what are you doing? You don't know how to fly!
Homer: I drove a car over a cliff once! How different could it be? (Looks out through the windshield.) Hmm, what's the ocean doing in the sky?
Mr. Burns: You saved my life! There must be something I can do for you.
Homer: (Thinks) A cookie! No, a car! No, a cookie!
Mr. Burns: You're getting a free dinner.
Mr. Burns: With...
Mr. Burns: ...Me!
Homer: Me? But that's you!
(Mr. Burns thinks to himself just before drowning.)
Mr. Burns: I guess this is the end. I just wish I'd spent more time at the office.
(Homer pays a private jet pilot.)
Homer: Okay, so this should be enough money to get me up in the air, have a frank talk with Marge, then maybe eat a deviled egg.
Pilot: Well, anything for a fellow Marine.
Homer: (Salutes) Yeah, Semper fudge.
Pilot: Uh, did you just say "Semper fudge"?
Homer: No, I said the right thing.
(Homer arrives home after his first day on the "new" job.)
Marge: So, how was your first day at your new job?
Homer: Oh, it was great! Flew to Tulsa on the company jet. Did my job in a way consistent with I what I already told you. (Nervously) Because that's what you do... when you have a job.
Lisa: I'm so proud of you, Dad!
Homer: Stop peppering me with questions!
Mr. Burns: (to Homer) Now let's enjoy the Miami of Canada -- Chicago!
(Smithers helps Mr. Burns shop for a cell phone.)
Smithers: What happened to that mini-cell phone I gave you, sir?
Mr. Burns: Ooh, I thought that was a lemon drop.
(Mr. Burns stomach suddenly vibrates.)
Smithers: I'll go get the number de-listed.
Unlike other episodes that have Homer's D'ohs in the title, this one doesn't have it replaced with the expression "(Annoyed Grunt)."
Itchy & Scratchy: "Come Flay With Me" Scratchy suffers the perils of commercial airlines as he is inadvertently mauled and maimed on a plane full of mice. Then Scratchy screams as a stewardess explains that they all have to spend 3 more hours on the tarmac before the plane can takeoff.
The episode's opening sequence is different from the one that's usually seen, as it shows Springfield in a rebuilding stage as a result of the events from The Simpsons Movie. As Bart skateboards home, a mutated multi-eyed pink squirrel with fangs jumps onto his shoulder, only to get knocked off by a wrecking ball before it attacks him. Mr. Burns has his own construction company, indicated by a couple of signs, including a large billboard with the slogan, "Building cheaply. Charging dearly." Burns is pictured holding a pair of money sacks. Bart showboats, passing by President Schwarzenegger, Colin, Moe (dressed in a bathrobe and a pylon on his head), Russ Cargill and Boob Lady. Homer comes home with the silo he used for his pet pig's waste strapped on top of his car and the garage and house aren't quite rebuilt yet. The Spider-Man theme music is heard when Spider-Pig/Harry Plopper is sitting on the sofa when the family arrives. They sit down as Homer picks up the pig and cradles him, affectionately calling him "My summer love" as the pig oinks.
Blackboard Joke: I will not wait 20 years to make another movie.
Couch Gag: Plopper the pig is sitting on the couch, the family rushes in and sits next to him. Homer holds him and says "My summer love".
While preparing to bowl, Homer performs the moonwalk and spins around and ends on his toes, a la Michael Jackson.
Casper the Friendly Ghost
When Homer is driven to Monty's private plane, he exclaims "A p-p-private jet!" This is an allusion to the show Casper the Friendly Ghost, where those who see Casper exclaim "g-g-ghost!"
Ferris Bueller's Day Off
In Chicago, Mr. Burns and Homer enter a salon called Ferris Bueller's Day of Beauty, referencing the title of the 1986 film, Ferris Bueller's Day Off. When they leave the salon Homer and Mr. Burns are dressed and styled like Cameron and Ferris; two of the movie's main characters.
At the mall a Cost-Mo store can be seen in the background. The name of the store is a parody of the name of the real-life super-store giant, Costco.
The Second City
In Chicago Homer and Mr. Burns visit Second City Theater, where improvisational comedy is performed. The name of the theater is a homage to "The Second City" which is an actual improvisational comedy theater in Chicago where many famous comedians and Saturday Night Live performers got their first start. The performer wearing a Chicago Cubs ball cap is modeled after and voiced by Dan Castellaneta who also got his start at "The Second City" in Chicago.
E.T.: The Extra Terrestrial
Mr Burns shops at a cell phone store in the mall called, "Crazy E.T.'s Phone Home." The store name is a reference E.T.s famous line, "E.T. phone home," from the 1982 film E.T.: The Extra Terrestrial.
Delta Air Lines
The title of this episode is a play on the old Delta Air Lines slogan, "We love to fly, and it shows."
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