Donnie Fatso (S22, E09-473)

I like how there's a carrot in Fit Tony's hand, as though we wouldn't get that he's fit otherwise.

Plot Summary
It's New Years Day, but unfortunately for Homer, he gets pinned by a slew of Springfield's new laws meant to tax the hell out of people.  Piling up $1000 worth of fines, Homer gets advice from Moe to place a bribe at window #9 at the courtroom.  Homer tries to do so, but nobody is at the window at the time so he leaves his ticket and a bag with the word "bribe" on it at the window.  Of course, a short time later Homer is arrested for the bribe and is given a 10 year jail sentence.

Homer is about to begin his sentence when Chief Wiggum reveals a way Homer can get out early: become a mob informant.  Homer meets up with an agent of the FBI, who informs Homer he's been on Fat Tony's tail for 20 years, trying to catch him smuggling Belgian guns.  He wants Homer to get close to Fat Tony, wearing a Fonzie-like wig which contains surveillance equipment as a disguise.  With Tony and his cronies currently in prison, Homer is sent in as Nicky "Blue Pants" Saxophony, and befriends Louie after he 'defends' Louie from a 'guard' (the FBI agent).  Louie takes Homer's act as genuine, and soon introduces Homer to Fat Tony, who decides to break out of prison.  As the prison was made by the mafia, Tony quickly crumbles a nearby wall and the group easily escapes.

Tony and Homer become fast friends, but before Homer can get any closer, Tony wants Homer to whack Moe, who mistakenly believed Tony's innocent mis-dial was a prank call.  Tasking Homer to burn down Moe's Tavern, Homer is saved when Moe does the deed himself rather than install a ladies' room.  Tony doesn't see this and only assumes Homer actually did it, and therefore lets Homer into the family, a gesture Homer fully accepts.  Soon, though, Homer is taken to a dock where Tony tells Homer about a Belgian gun shipment that's about to come in.  Homer tries to warn Tony, and as authorities start moving in, Tony finally figures out that Homer was a rat.  Unable to deal with the betrayal, Fat Tony has a heart attack, and dies right there.

With the FBI agents rather cold towards Homer, Homer is let free and is able to go home.  Still, he can't let go of his time with Fat Tony, and visits his grave where he gets whacked with a shovel.  Upon coming to, he thinks he hears Fat Tony's voice, but its actually the voice of his cousin, Fit Tony who, as the name implies, looks like a much fitter version of Fat Tony.  Fit Tony planned on killing Homer, but after seeing Homer's genuine sorrow and grief towards Fat Tony's death, Fit Tony decides not to kill Homer, believing that Fat Tony's memory will live on in him.  Homer narrates the rest, as Fit Tony takes over the Springfield mafia.  However, Fit Tony has a hard time dealing with the pressure of being a mob boss, and starts overeating to lessen his woes.  Eventually, he gains enough weight to be called "Fitfat Tony" and then just "Fat Tony", even wearing the same clothes as the original one.  Still, Homer is glad to be back with his family even if the only person in said family to ever shoot a gun was Maggie.

Quick Review
I remember seeing this episode when it first aired, and I remember hating it.  I gave a pass to The Principal and the Pauper back in Season 9 for its blatant screw around with established canon, but for some reason having Fat Tony die only for him to be replaced by his cousin Fit Tony who ate so much he became the new Fat Tony just bugged me badly.

Watching it again, the episode isn't as bad as I originally thought it to be.  Leading up to the big moment, the episode actually fares pretty decent, as well as most other Season 22 episodes thus far anyway, and the segment where Homer infiltrates Fat Tony's crew was entertaining.  Hell, the moment Fat Tony dies wasn't bad either by itself, I didn't have a problem with that and the gag with Homer's self-destructing hair added a nice but not overboard comical touch to it.

Still, though, the inclusion of Fit Tony, and using him to maintain a Fat Tony character for future episodes seems like such a cop out, even by Armin Tamzarian standards.  Its like the writers wanted to make an impactful episode, complete with a characters death, this time with meaning unlike a previous episode, yet they were mandated not to kill anyone off so they threw together a nonsense of an ending to keep canon intact, even though it loses all of the impact of the death.  It seems so pointless and it just ruins the episode.

Final Score: 6.4

The Trouble with Trillions (S09, E20-198)

"American tax dollars will help our allies, who fought
so poorly, and surrendered so readily."

Plot Summary
Though Ned Flanders is able to send in his tax return on the first day of the year, it seems like nobody else even tries to get theirs in early as, on the final hour of tax day the post office is swamped with people who have yet to file.  This includes Homer, who doesn't realize that that forms he sent in last year don't count for this year.  In a panic, he balls up a poorly done tax return and is able to bounce it into the mail bin at the very last second.  However, the return then bounces its way into an audit bin, and Homer is in trouble.

Homer is taken in by the IRS but then handed over to the FBI, as now he is forced to work for them to pay off his tax fraud.  Wearing a wire, he's able to help the government bring in a couple of people for conspiracy, however his job isn't done.  Now they want Homer to go on a high risk mission, using an old video to explain it.  After World War II, President Truman ordered the creation of a trillion dollar bill to aid his European allies.  Delivery of the bill was tasked to Monty Burns, who as the richest American at the time was also the most trustworthy to deliver the bill.  Of course, the bill went missing, causing those European allies to act snooty to Americans forever.  Homer is tasked to go to Burns' mansion and find that bill.

Homer is able to gain access as the hounds have gone missing and Burns can't scald Homer properly.  As Homer tries to look around for the bill, Burns spots him, believing him to be a magazine writer.  Home goes along with that story and is given a tour of Burns' mansion.  At a special "patriot" wing of the house, there's a model of Burns himself holding a replica of the bill, having 'saved' it from being squandered.  He reveals the real bill to Homer, but just then the FBI agents come in to arrest Burns.  Burns goes on a tirade about how tax dollars go to waste all the time, which convinces Homer to knock out the two agents and grab both Burns and the bill before escaping.

The two grab Smithers from his apartment, who informs them that they should probably leave the country for awhile.  They're able to do so via a plane, and now agree to just find an island and buy it with the trillion dollars.  Burns comes across an island, but it turns out to be Cuba which he crashes the plane into.  Shocked that Batista is no longer in power, Burns demands to see whoever is in charge to discuss buying Cuba.

As it turns out, Cuba is bankrupt, and though Castro and friends had their fun with communism, they're willing to cede defeat to American.  Just then, Burns arrives with his money.  Castro is able to convince Burns to let him 'see' the bill, but suddenly it disappears on him and Burns is out a trillion.  On a makeshift raft back to America, the three agree that America is at least a better country than Cuba, and that Burns is more than ready to bribe a jury to escape his charges.

Quick Review
This episode goes in a couple of different directions, but once it settles into the trillion dollar bill plot it turns out to be an excellent episode.  The backstory behind the bill as well as Burns' adventure in Cuba make for the high points of the episode.

Final Score: 8.9