Halfway home in the Top 40 List.

#25: Lisa’s Wedding

Original Air Date: March 26, 1995

PLOT: A fortuneteller tells Lisa about her future romance with a British classmate in the year 2010.

What I love about this episode is, obviously, the flash forward to a different time in the Simpsons lives. I believe this is the first time we’ve ever gone into the future and its one of the more solid episodes of the type.

Lisa-centric episodes are usually pretty solid on the heart aspect, but this one is still pretty laugh-out-loud funny. The writer’s have a great time making up the differences of life in the far-off year of 2010. From robots all over the place to hologram trees, they really do the future right. The exploding robots still get me every time.

It’s also balanced nicely by a sweet ending in which Lisa realizes how important her family is to her, for better or worse. Like I’ve said, Lisa episodes are always good for a touching story and this one has a nice little ending.

Great voice-work by Mandy Patinkin here as Hugh. He’s nearly unrecognizable in his role and those are the guest performances that I truly love: a celebrity that isn’t just playing themself but is creating an actual voice for the character (see: Meryl Streep as Jessica Lovejoy). Hugh is a bummer of a loss for Lisa because he is a good pairing for her, but the Simpsons prove too much for him, which is understandable if not disappointing.

#24: Radioactive Man

Original Air Date: September 24, 1995

PLOT: Milhouse is cast as Fallout Boy in the new Radioactive Man movie, as the rest of the town gets enamored with movie-making.

This is a great Milhouse episode, who up until this point, save for the episode ‘Bart’s Friend Falls in Love’, is more or less a comic foil for Bart’s schemes. Milhouse is one of my favorite characters and its primarily because he a walking punchline, but the character turn here is phenomenal.

This is a character study about a reluctant protagonist coming to grips with unwanted fame. To put on the shoulders of an innocent child such as Milhouse gives this reluctance merit and heart. It is one of the most heartfelt storylines involving a secondary character in the entire run of the series.

Outside of Milhouse’s arc, there is a hilarious B story about the entire town gouging the film crew left and right. It’s a chance for the writers to snarkily poke fun of the things they dislike about Hollywood.

Also, this episode has a great guest appearance by Mickey Rooney, the biggest box office draw from 1939 to 1940. (Wow! Spanning two decades!)

#23: El Viaje Misterioso de Nuestro Jomer

Original Air Date: January 5, 1997

PLOT: Homer eats a Guatemalan Insanity Pepper at a chili cook-off that takes him on a spiritual journey of self-reflection.

Very few episodes of this series pushes the limits of the medium quite like this one. The Simpsons, despite being animated, are grounded in a reality rarely seen in animation. Its contemporaries like South Park and Family Guy asks more of a suspension of disbelief than the Simpsons do. But in this particular episode, the restrictions of reality are torn down and the animators and writers are given the freedom to do just about anything.

This is a FANTASTIC character episode for Homer. Few episodes reach the emotional depths this episode puts him through. As he spends the entire second act in a foreign world, its basically a one-man show of discovery, both of this alien setting and of himself. As always Dan Castellaneta’s voice-work is masterful as this is an episode that requires a ton of range out of Homer.

The animation is also at the top of its game here. This episode is really a showcase for what 2D animation can do. Homer’s spiritual journey is a work of art inline with a Salvador Dali painting brought to life.

#22: Lisa’s Rival

Original Air Date: September 11, 1994

PLOT: Lisa becomes obsessed with a rivalry between her and a new girl at school; one that seems slightly better than her in every way.

Again, another fantastic Lisa episode. The writers consistently create amazing storylines for the middle child of the clan. This one is surprisingly darker than the other ones where she is the focal point.

For the first, and probably last, time in the series, Lisa is shown as seriously flawed. She’s overcome with jealousy by Allison, played by Winona Ryder in a great guest appearance. Allison is seemingly perfect and bests Lisa in almost everything she holds dear: grades, music, etc. What unfolds is Lisa’s obsessive attempt to prove her worth versus this new competition, going as far as enlisting the help of Bart to humiliate the girl at Diorama-Rama.

One of the crowning moments of this rivalry is when Lisa is invited to Allison’s home and is introduced to her father; a man who enjoys a good anagram. Lisa is made to look foolish when Allison proves better than Lisa once again, leaving Allison’s father without words. “Here’s a ball… perhaps you’d like to bounce it.”

#21: Lemon of Troy

Original Air Date: May 14, 1995

PLOT: The boys of Springfield are hit with town pride as they band together to take back a Springfield lemon tree from rival Shelbyville.

I love Bizarro episodes and this is one of my favorites. Its always interesting to see the animators’/writers’ perception of what the opposite of their characters are. In this one you, you not only get to see the Bizarro Homer and Bart, but also a Bizarro Milhouse and Bizarro Duff beer. Truly priceless to see.

Its cool to see the Simpsons do a bit of a take on the Men on a Mission story and it lends itself for some great pairings (Nelson and Martin as Team Discovery Channel). Its just one of the things that is great about the Simpsons: the rich assortment of background characters that once in a while get to share the spotlight. This is also a very strong episode for Milhouse and he has some of the greatest moments in the episode.

One thing that stands out to me about this episode is my personal experience with it. I remember sitting in a class with a friend of mine senior year of high school reciting the dialogue of the Shelbyville Homer. I was really cool in high school… But seriously, I did a dead-on imitation.