14. “The Greatest Story Ever D’ohed” – Original Air Date: March 28, 2010
Not only is this the worst vacation episode, it might be the worst Simpsons episode ever. Homer is painfully annoying even compared to his usual standard, and Sasha Baron Cohen plays the most irritating tour guide ever. Every line he delivers, you want to punch him a little more. Watch this episode once out of curiosity, and then never speak of it again.
13. “In The Name Of The Grandfather” – Original Air Date: March 22, 2009
This one is just so freaking boring. The family goes to Ireland because…Grampa used to live there or something. Like most of these travel episodes, there’s a bunch of scenes featuring the family doing a things related to the culture of whatever country they’re in, but in this case, it just feels uninspired, with the Blarney Stone bit (where Marge just keeps talking endlessly) being particularly stupid. The only memorable jokes here were the Yuppie Leprechauns and the ad for the U2 moving company (“We Move In Mysterious Ways”). Other than that, this episode can be very quickly forgotten.
12. “Dude, Where’s My Ranch?” – Original Air Date: April 27, 2003
The first act, which features “Everybody Hates Ned Flanders,” and a cameo from David Byrne, is pretty funny. After that, this one isn’t anything to write home about. The Simpsons go to a dude ranch where they do a bunch of dude ranch stuff, and Lisa falls in love with a 13 year old and briefly turns into a psychopath. Then, the episode ends without anything really significant happening, and you’re wondering where those precious 22 minutes went.
11. “The Regina Monologues” – Original Air Date: November 23, 2003
The Simpsons goes to England and…meh. Other than the Trainspotting parody where Bart and Lisa become junkies for British candy, this episode is just kind of ordinary. Homer acts like a huge jerk and nearly gets the family killed because that’s just what he does, and the plot with Grampa’s lost love from World War II was done far better on King Of The Hill. There’s nothing egregiously bad about this episode, but it feels like a lot of wasted potential. Honestly, the first act with Bart finding the thousand dollar bill is probably funnier than anything that happens in England, and that just doesn’t make sense. Pretty much every scene is a celebrity cameo, and with the exception of Ian McKellen’s Macbeth bit, none of them are all that funny. This episode could have been so much more.
10-9 (tie). “Kill The Alligator And Run” – Original Air Date: April 30, 2000/”Simpson Safari” – Original Air Date: April 1, 2001
I’m including these two episodes together because, well, they’re kinda the same episode. Both episodes have a fair amount of good jokes, but are severely hampered by plots that make no sense, and change direction about five different times. Plus, Homer is painfully annoying in both of them. Neither one is quite as bad as you’ve likely heard, but both could have been much stronger episodes with a little more cohesion. They’re about even in quality, but I’ll give a slight edge to the Africa episode because Kid Rock isn’t involved.
8. “Goo Goo Gai Pan” – Original Air Date: March 13, 2005
The Simpsons go to China so Selma can adopt a baby, and Homer has to pretend to be her husband. This premise would grow thin pretty quickly, but thankfully, the episode focuses more on the family’s adventures in China than anything else. Homer trying to be an acrobat — and ruining everything — is pretty funny, and apparently causes a revolution (“I’m going to question every thing now! Why doesn’t Pearl Jam ever come here?”). This isn’t the strongest vacation episode, but the series of vignettes that make it up are pretty funny, and it’s nice to see Homer do something nice for Selma for once.