Milhouse Mussolini Van Houten is best known as Bart’s best friend on The Simpsons. He goes along with Bart’s antics but is often more cowardly compared to his fearless companion. Milhouse also has a complicated relationship with Lisa, who more often than not rejects his advances.
There are a lot of episodes in the long-running animated sitcom that focus on Milhouse’s misadventures, chaotic family, and troubles at Springfield elementary. The best Milhouse episodes highlight what makes him such an important character on the show. These are usually from the earlier seasons of the sitcom, which are often considered to be the golden age of The Simpsons. The worst ones are predictably from the later seasons, as they have been criticized for Milhouse’s uncharacteristic actions and pointless storylines.
"Little Orphan Millie" (Season 19, Episode 6)
Things seem to be going well for Milhouse’s parents in “Little Orphan Millie,” so well in fact that they decide to take a cruise together. This ends in disaster when they fall off the boat and are declared dead, which causes Milhouse to become depressed. He ironically becomes more popular than Bart because of his newfound hopelessness. Meanwhile, Marge and Homer dominate the episode’s subplot when the protagonist’s wife gets angry about her husband not being able to the color of her eyes.
It’s easy to see why it’s not a fan-favorite episode, as major characters like Milhouse and Marge act out of character. It’s also fast-paced, which means it skips over the nuances of Milhouse’s relationship with his parents, as well as the details of Kirk and Luann’s complex partnership.
"Milhouse Of Sand And Fog" (Season 17, Episode 3)
When Milhouse realizes he doesn’t get nearly as much attention when his parents are together compared to when they’re separated, he hatches a plan with Bart to break them up. The comical chain of events in “Milhouse of Sand and Fog” almost leads to the heartbreaking separation of Homer and Marge instead but this is thankfully averted in the end.
It’s a messy episode that relies on viewers’ attachments to the characters’ relationships by threatening to ruin them. There are a few funny moments, like when Milhouse’s bad eyesight causes Bart to fall into the rapids, but these don’t make up for the stressful scenes scattered throughout the episode.
"Homer Scissorhands" (Season 22, Episode 20)
“Homer Scissorhands” is a hidden gem in the sitcom’s often-criticized later seasons. It tells two stories, with the first showing Homer’s impressive talent as a hairdresser, and the second following Milhouse’s attempt at starting a relationship with Taffy after Lisa’s rejection.
Lisa becomes obsessed with Milhouse and Taffy’s relationship and unintentionally ruins it. This prompts a surprisingly moving speech by Milhouse where he asks her if she really wants him to be miserable. Overall, it’s a decent episode with clear storylines, but it’s nothing too special. It’s somewhat disappointing that Taffy’s character is underused, though, as Kristen Schaal did a wonderful job of voicing her.
"The Good, The Sad And The Drugly" (Season 20, Episode 17)
“The Good, the Sad and the Drugly” follows Bart’s attempts at wooing Jenny, much to Milhouse’s disapproval. He was expecting Bart to come visit him at home, as Milhouse was blamed for one of his silly pranks in Springfield Elementary. There’s a subplot that focuses on Lisa’s increasing dependence on the antidepressant, “Ignorital.”
Unfortunately, neither of these plots are new. Bart has previously tried to start a relationship with a girl named Jessica, which also annoyed Milhouse. Lisa’s subplot is similar to Homer’s use of medical marijuana, but with a much darker undertone. One of the few things that saves the episode is Milhouse’s hilarious overdramatic reaction to Bart’s betrayal.
"Hardly Kirk-ing" (Season 24, Episode 13)
For some fans, Kirk is an annoying recurring character on the show. This is why it’s a pleasant surprise to see Milhouse’s take on his own father’s personality in “Hardly Kirk-ing,” as it makes fun of how much they’re alike.
He dresses up like his father and even sounds like him thanks to a tight necktie. Bart and Lisa use Milhouse’s disguise to do things only adults can, which include buying cigarettes and going to a hotel on their own. It’s a wacky episode with an original story, with its major downside being its boring subplot. They could’ve skipped Marge’s qualms about the TV and Homer’s obsession with a picture book entirely, as they take away from Milhouse's entertaining storyline.
"Milhouse Doesn’t Live Here Anymore" (Season 15, Episode 12)
The episode “Milhouse Doesn’t Live Here Anymore” spotlights how important the character is to Bart. Things drastically change for Bart when Milhouse moves to Capitol City and changes his personality. He sports comically spiky hair and a bad attitude, much to Bart’s dismay.
Bart and Lisa end up becoming best friends, as they realize they can have fun together. There’s a poignant moment in the end when Milhouse returns and Bart promises Lisa that she still matters a lot to him. It’s too bad they didn’t end it on a sentimental note, as the show squeezes in a disappointing joke that ruins the sweetness. Other than that, though, it’s great to be able to see another side of Milhouse’s personality and more of his family’s chaotic decisions.
"Bart’s Friend Falls In Love" (Season 3, Episode 23)
Bart tries and fails to convince Milhouse that he’s making a questionable dating choice when he gets together with Samantha in “Bart’s Friend Falls in Love.” They’re actually a really good match and Bart is obviously just envious because Milhouse is happy with someone else. There’s also a brilliant subplot that focuses on Homer’s vocabulary improvement.
It’s a classic episode that highlights the strong bond between Bart and Milhouse. It’s both funny and sad to see Bart feel so lost without his best friend. While it feels as if Milhouse’s story is sometimes overshadowed by the fascinating subplot, it’s not so distracting that viewers would lose interest in the main narrative.
A Milhouse Divided (Season 8, Episode 6)
Fans are introduced to the inner workings of Kirk and Luann’s messy relationship in “A Milhouse Divided” after Milhouse’s mom declares she wants a divorce. Milhouse is predictably caught in the middle and generally has a terrible time as his mom and dad both start dating other people.
There’s a moving subplot that features Homer’s unwavering love for Marge, which leads him to file divorce papers for the sole purpose of marrying her again. It’s definitely one of the best episodes of the show, but Milhouse’s reactions aren’t as highlighted here as they could’ve been. Nevertheless, it’s an episode that’s part of the important foundation of Milhouse’s character, as it provides viewers insights into his complicated home life.
"Bart Sells His Soul" (Season 7, Episode 4)
While the episode “Bart Sells His Soul” arguably focuses on Bart more than Milhouse, it’s Milhouse who makes it truly entertaining. When Bart gets reprimanded in church after a prank, Milhouse dares him to sell his soul, which the prankster soon regrets.
The way Milhouse keeps the piece of paper and torments Bart throughout the episode is hilarious, as it seems as if he knows it’s meaningless. It draws attention to how much smarter Milhouse is compared to Bart, especially when he wants to be. Things work out in the end as Lisa unsurprisingly fixes Bart’s problem and Milhouse is left with just one soul.
"Radioactive Man" (Season 7, Episode 2)
If there’s one episode that really makes Milhouse shine, it’s “Radioactive Man.” It follows Milhouse’s misadventures when he’s cast as “Fallout Boy,” Radioactive Man’s sidekick for the film. Bart is extremely jealous of him because of this, but it turns out Milhouse doesn’t even want the role.
Fans learn more about what Milhouse values through this thoughtful and funny episode. He doesn’t like what his potential fame and fortune do to his parents, and he’d rather hide in Bart’s treehouse than go out in front of a crowd. This storyline likely causes fans to feel sympathetic for Milhouse who, at the end of the day, just wants to be a kid and hang out with his best friend, Bart.