Marge Simpson, Patty Bouvier, and Selma Bouvier
Mr. Burns, Ned Flanders, Principal Skinner, Waylon Smithers, Kent Brockman, and others
Homer Simpson, Grampa Simpson, Barney Gumble, Krusty the Clown, Groundskeeper Willie, and others
Bart Simpson, Nelson Muntz, Ralph Wiggum, Todd Flanders, and others
Apu Nahasapeemapetilon, Moe Szyslak, Chief Wiggum, Comic Book Guy, Lou, and others
Maude Flanders, Helen Lovejoy, Miss Hoover, and others
Agnes Skinner, Brandine Del Roy, Dolph and others
Milhouse Van Houten, Rod Flanders, Jimbo Jones, and others
In Moe's Tavern, Lenny tells the bar gang (when asked by Moe) that if he was granted one wish by the Pope, he always wondered what it would be like to wear something ironed, to which Moe and Carl also marvel at the thought. Later, in the same episode, Mr. Smithers is ironically seeing ironing his socks, of all things, when Mr. Burns and Homer arrive seeking his assistance.
The movie that Homer and the FBI agent saw in the photo booth is rated TV-PG.
We find out that the Sailing Boat painting that hangs above the couch was painted by Marge.
Homer: (On the phone) Oh, you're going to love it in Cuba, Marge. There's shredded pork everywhere.
Cuban Boy: Es carne de burro.
(Translation: "It's donkey meat")
Homer: Nice to meet you!
(After flying to Cuba)
Mr. Burns: Sorry about the landing, boys. This fog is so thick I can't see my own cataracts.
Homer: (Filling out his tax return) Okay, Marge, if anybody asks, you require 24-hour nursing care, Lisa's a clergyman, Maggie is seven people and Bart was wounded in Vietnam.
Mr. Burns: I'm not the thief; the government is. Every year you make hardworking Joes like my reporter friend pay income taxes. And for what? Aid to ungrateful foreigners, do-nothing nuclear missiles, tomb polish for some unknown soldier.
Mr. Burns: That intrepid lad is my great-grandfather, Franklin Jefferson Burns, tossing that without a care for what the caffeine would do to the Finway Flounder.
Homer: Is that a fish?
Mr. Burns: It was.
Mr. Burns: (Pointing to a display case) Oh, you'll find this amusing: the suit Charlie Chaplin was buried in.
Homer: (Wearing an FBI listening device.) Hey, see you're watching the ball game. Looks like a good one. Any of you involved in any illegal activity? Cause I could sure go for some. How bout you, Lenny? Testing, testing. Lenny?
Lenny: You saying you want to commit a crime, Homer?
Homer: Maybe. But first I need to hear about some other crimes to get me fired up.
Carl: You mean like the time you was running moonshine out of your basement?
Barney: Or that telemarketing scam you pulled?
Homer: Uh . . . like those, but involving you.
Moe: Oh, you mean like the time Barney beat up George Bush?
Homer: Barney!? That was me! And I'd do it again.
Charlie: Why stop there, Homer? My militia has a secret plan to beat up all sorts of government officials. That'll teach them to drag their feet on high definition TV!
FBI Agent: You're under arrest for conspiracy!
Moe: How'd they finger Charlie? Somebody must have ratted him out.
Homer: Oh, that's ridiculous, Moe. End transmission.
Homer: Does this make me look fat?
Lisa: No, it makes you look like a tool of government oppression.
Homer: But not fat?
Lisa: The government has no right to use you this way.
Homer: Quiet, honey, you don't know how big this government is. (whispering) It goes all the way to the President.
Gil: Oh, this is bad, this is really bad. You work and you slave and you steal just enough for a sweet lick at that shiny brass ring. Don't I get a lick? Doesn't Gil get a lick!?
IRS Agent: Simpson, Homer J.
Gil: Hey, put in a good word for old Gil would ya?
Chief Wiggum: (addressing a crowd) All right, people, listen up: the harder you push, the faster we will all get out of here.
Rod: Daddy, what do taxes pay for?
Ned: Oh, why, everything. Policemen, trees, sunshine. And let's not forget the folks who just don't feel like working, God bless 'em.
Maude: Neddy, it's 8:45; the post office is going to be opening soon.
Ned: 8:45!? Here I am yapping away like it's 8:35!
(Homer checks out the trillion dollar bill)
Homer: Wow, that must be worth a fortune.
(Agent Johnson asks Homer to go for a walk with him)
Homer: Walk? That wasn't part of the deal!
FBI agent: You won't be seeing any prison movies where you're going--Prison!
Homer: If I don't hear you, it's not illegal!
(Homer is confronted by the IRS)
Homer: I know sir, I'm sorry sir, an older boy told me to do it.
Homer: Look at those morons! I paid my taxes over a year ago!
Mr Burns: See with your eyes, not with your hands!
Fidel Castro: Please! We are all amigos here!
Homer: Mr. Burns, I think we can trust the President of Cuba!
(Mr. Burns reluctantly hands over the money)
Mr. Burns: Now give it back.
Fidel Castro: Give what back?
FBI Agent: (In photography booth) Mr. Simpson, please cover your eyes while I say the secret access word. Cheese!
Moe: Hey Lenny, let's say you pull a thorn out of the Pope's butt and he grants you one wish. What'll it be?
Lenny: Uh...only one huh? Well, I've always wondered what it would feel like to wear something that's been ironed.
Carl: Oh that would be sweet!
Marge: I put the tax forms on the top of your "to do" pile a month ago!
Homer: I have a "to do" pile!?
Kent Brockman: Sir, why did you wait until the last minute to pay your taxes?
Otto: Taxes!? Isn't this the line for Metallica?
Kent Brockman: Sir uh...why did you wait until the last minute to pay your taxes?
Krusty: Because I'm an idiot! Happy!?
(All of Springfield is watching the ball drop and counting.)
Springfield: 10, 9, 8...
(The ball gets stuck)
Springfield: 8, 8, 8!
Homer: Oh will this horrible year never end!?
Chief Wiggum: We've never lost a year before, and I'll be damned if we're gonna lose one on my shift!
(Wiggum shoots the ball and it falls)
Springfield: (Rapidly) 7, 6, 5, 4, 3, 2, 1!
Smithers: But, sir, what about your criminal charges?
Mr. Burns: Well, if it's a crime to love one's country, then I guess I'm guilty as charged. And, if it's a crime to steal a trillion dollars and hand it over to communist Cuba, then I guess I'm guilty of that, too. And, if it's a crime to bribe a jury, God help me, I'll soon be guilty of that as well!
Homer: God bless America!
Mr. Burns: That's odd; a pack of vicious dogs should be tearing you to pieces by now.
Homer: I don't know what to tell you.
Mr. Burns: Well, come inside. Maybe I can scald you with something.
(Mr. Burns, Smithers and Homer are looking for an island to create a new country in.)
Mr. Burns: Look at that island. That looks free enough.
Smithers: Sir, that's Cuba!
Agent Johnson: We believe Burns still has the bill hidden somewhere in his house, but all we've ascertained from satellite photos is that it's not on the roof.
FBI Agent: From now on, you're working for us.
Homer: Okay, but could you pay me under the table? (Whispering) I've got a little tax problem.
Mr. Burns: Take her down, Smithers.
Smithers: Sir, you're flying the plane!
Mr. Burns: Excellent!
Castro: We all knew from day one this mumbo jumbo wouldn't fly!
Blackboard Joke: I will not demand my worth.
Couch Gag: The TV room is used as a sauna by three old men. One of them pours water over the hot rocks. The family come in with towels on, notice the men, and leave.
Wiggum: We've never lost a year before, and I'll be damned if we're gonna lose one on my shift!
This is similar to a line from the 1995 movie Apollo 13, in which Flight Director Gene Kranz (Ed Harris) says, "We've never lost an American in space and we're sure as hell not gonna lose one on my watch!"
Smithers: (singing to himself) You'll be swell! You'll be great!
This is a line from the song "Everything's Coming Up Roses" from the musical/movie Gypsy.
The title of the episode alludes to the title of a famous Star Trek episode "The Trouble with Tribbles."
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