The 5 Best Milhouse Episodes On The Simpsons, Ranked

The voice of Milhouse is leaving after season 35 of “The Simpsons.” Pamela Hayden has been a part of the long-running series since the first season aired back in 1989 and also voices Jimbo Jones, Rod (and sometimes Todd) Flanders, and Chief Wiggum’s wife Sarah. Now, however, fans of Milhouse will surely be feeling conflicted about one of the show’s best characters being voiced by another actor.

Rather than dwell upon what is truly the end of an era for “The Simpsons,” however, why not celebrate the legacy of Hayden’s Milhouse? The boy whose mom says he’s cool; who knows far too much about the various types of sprinklers; who’s had his picture on “America’s Most Wanted” and was subsequently hunted by the FBI before jumping from a dam to what would have been certain death (he only broke his glasses), has been provided some of the best moments in the show’s long history. But he’s also been at the center of some of the best ever episodes of “The Simpsons,” consistently proving he’s much more than a peripheral character good for a few gags here and there.

Naturally, there are a ton of episodes featuring Milhouse that didn’t make the cut here. The unimpeachably perfect “Lemon of Troy” or “Bart on the Road” are two examples. But that’s okay because the Vanhoutens’ son has been the focus of dozens of classic “Simpsons” installments. So come along as we celebrate Bart’s best friend in a list where legitimately everything’s coming up Milhouse.

Milhouse was frequently the butt of whatever joke the writers needed him for, but back in season 3, he hadn’t quite become the running joke of a character he later would. Episode 23 of that season, “Bart’s Friend Falls In Love,” is a good example. This is the episode where, much to Bart’s dismay, Milhouse actually gets a girlfriend in the form of Samantha Stanky (Kimmy Robertson). It’s also the episode that features one the greatest film references in the show’s history, with the opening sequence perfectly recreating Indiana Jones’ legendary plundering of the Temple of the Chachapoyan Warriors and its “golden idol in “Raiders of the Lost Ark”.

“Bart’s Friend Falls In Love” isn’t packed with gags at Milhouse’s expense, though we do learn that he cries when he does long division and he has a remainder left over. But it remains great because like so many early “Simpsons” episodes, it combines its brilliant humor with surprising emotional depth. The episode is driven by a story that should ring true for anyone who remembers having a best friend as a kid. Bart’s jealousy over his friend’s newfound love feels so accurate to how a 10-year-old would react and actually reveals a deep fondness for Milhouse on Bart’s part. By the time the pair reconcile and leave Samantha at her Catholic school to go whip donuts at old people, you realize that “The Simpsons” has once again managed to make you feel a little something between the gags.

In 1995, three years after “Bart’s Best Friend Falls in Love,” we got yet another reminder that Milhouse actually has feelings like the rest of us with season 7, episode 2, “Radioactive Man.” A standout episode in its own right, this installment sees Milhouse cast as the titular hero’s sidekick, Fallout Boy, with Bart once again becoming jealous of his friend after missing out on the role. It’s full of memorable moments, from Luann Vanhouten’s jacuzzi suit to Rainier Wolfcastle’s immortal “My eyes, the goggles do nothing.” But it also reminds us that Milhouse isn’t a one-dimensional character who’s good for a laugh now and then. 

His struggles with his burgeoning stardom feel like the one grounding element in what is an otherwise ridiculous (and hilarious) episode. “Radioactive Man” also reminds us that Milhouse’s parents aren’t always the most attentive, with the aforementioned jacuzzi suit preventing Luann from hearing her son’s concerns over being cast in a Hollywood production. Moments like this also help set up what is an all-timer of an episode in the following season.

“Radioactive Man” is great for so many reasons, but it’s a top Milhouse episode for showing us that while the character might be a bit of a dweeb, he’s at least not shallow enough to be taken in by stardom and its trappings, even while everyone around him is.

Seasons 6, 7, and 8 of “The Simpsons” not only included a historic run of Milhouse episodes, but they’re also notable for just how much abuse the character suffers throughout. Season 7 sees him poking at the controls of a fighter jet in “Sideshow Bob’s Last Gleaming,” raging against his parents’ decision to put him in therapy and announcing “Take that Dr. Sally Waxler” before unwittingly ejecting himself into the troposphere. Season 8 saw him beaten into unconsciousness by Nelson, who’d misinterpreted a romantic note from Lisa, leading to that classic, “He can’t hear you now, we had to pack his ears with gauze,” moment. 

But there’s no episode that has quite as much fun absolutely roasting Milhouse as “Summer of 4ft 2.” Though this is really a Lisa episode, the season 7 installment is also packed with classic jokes at Milhouse’s expense, beginning with his, “Which kind of sprinkler do you like?” run that prompts Bart to implore his friend to “try to have some dignity.” But such a thing eludes Milhouse for the rest of the episode, as the writers simply refused to let up on the poor guy.

After the family vacations in Little Pwagmattasquarmsettport (America’s scrod basket), Bart fails to wow Lisa’s new friends, leading Milhouse to ask, “Are we down with ’em?” only for Bart to curtly respond with, “No, they must’ve seen you!” Later, when the family plays a board game and Bart pulls the “dud” card, Homer doesn’t hold back in mocking Milhouse for looking exactly like the poor sap on the card: “Hey, he looks just like you, Poindexter!” The kid is so overlooked, that he’s even shown hiding behind a cereal box for the duration of breakfast, only revealing himself when he hears news of a carnival — at which he’s covered in spit from both Bart and Lisa as they try to trade loogies on the carousel. It might not be a Milhouse episode in the most obvious sense, but “Summer of 4 ft. 2” is one of the character’s most hilariously tragic moments.

An all-time great “Simpsons” episode, “Bart Sells His Soul” is also notable for giving Milhouse the upper hand for once. While season 7 would end with all-out Milhouse ridicule in “Summer of 4ft. 2,” it actually started off with the character getting one up on his best friend, demonstrating a touch of nous that previously hadn’t been all that evident.

For one, Milhouse convinces Bart to sell his soul (a piece of paper with “Bart Simpson’s Soul” written on it) for five bucks, only to then demand 50 bucks when his friend wants it back. The maniacal laugh Milhouse lets out in that particular moment is truly unhinged and an example of Pamela Hayden’s unique ability to surprise in her performance, even with a character she had, at this point, played for seven years.

Though the episode is undeniably Bart-focused, Milhouse’s scenes are some of the best and give us a glimpse of the character’s cunning — a trait that could easily have seemed unsuitable for a character that is frequently the butt of the joke, but which somehow seems to work as a propellant for a kind of “Milhouse gets his own back” story.

“A Milhouse Divided” combines some of the series’ best jokes with a grounded storyline that is both hilarious and full of heart. It also happens to be the best Milhouse episode.

Marge and Homer’s elegant cocktail party is quickly ruined by the palpable tension between Kirk and Luann VanHouten, who end up separating as a result of their barely concealed resentment toward one another. This bickering between husband and wife (which comes across as a little too realistic) is contrasted against charming scenes of Milhouse just being a kid as he plays with the other children upstairs, completely unaware that his family is fracturing. Rather than being the butt of the joke, this time around you actually feel bad for Milhouse, who has clearly been the unwitting victim of his parents’ squabbling for some time. As such, for all its brilliant gags, the episode starts out on quite a tragic note, which resonates throughout the remainder of the runtime.

As the episode goes on, we get such legendary lines as “I sleep in a big bed with my wife,” “That’s Jerry, he’s a major player down at the sewing store,” and “I don’t recall saying ‘Good luck’.” Then, of course, there’s Kirk’s classic “Can I Borrow a Feeling” cassette tape that Homer relentlessly mocks. But in between it all is Milhouse, who this time around escapes such relentless mockery and is given a chance to just be a vulnerable kid who struggles with his parents’ divorce. It’s that classic combination of humor and heart once again, reminding us that, as Kirk sings, “Hurtin’ hearts need some healin’,” and making us all want to take Milhouse’s hand with our “glove of love.”