Havana Wild Weekend (S28, E07-603)

This was funnier than any of the Cuba scenes, honestly.

Plot Summary
Grampa is having bladder problems, causing him to be more depressed than usual.  He goes to a VA hospital for help, but as the writers remain 18 months behind the times, they still think the problems with the VA are a hot topic, so as a result Grampa isn't getting help anytime soon.  Fortunately, another vet directs Abe to getting help in Cuba, where medical care is both fast and cheap.

However, upon arriving, doctors there provide no additional help.  Abe is about to give up on life until he spots a 1950s era car that populate the country.  Reinvigorated by nostalgic sights, Abe befriends a female bartender who takes an interest in him, as well as an old war friend who has been hiding out in Cuba for decades.  The friend invites Abe to help operate his hidden business - a hijacked plane which is now used for parties.  Abe decides to stay and the other Simpsons return home without him.

Not pleased with these turn of events, Homer strikes a deal with the CIA to retrieve Grampa in exchange for some baseball players.  Meanwhile, Grampa and his friend host a party full of shady characters who have found refuge in Cuba to avoid legal troubles.  As Homer and family find and try to convince Grampa to leave, the bartender whom he befriended (and invited to this party) hijacks the plane.  She's actually an undercover CIA agent who used Grampa to weed out and recapture the various criminals that came to the party.  Afterward, Grampa is again depressed that his life no longer has meaning again but Homer invites him to the golf course so that the two of them - and Bart - can take part in the ancient past time of messing with golfers.

Quick Review
This wasn't a great episode.  This reminds me a bit of the Brazil episode - though the jokes did work better here there was also a lot of cultural and modern references that just don't do anything to add to the episode other than serve as a constant reminder that "oh yeah, they're in Cuba".  Which, as I've mentioned before, does not work as any real comedy.

Final Score: 5.7

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