It’s truly the end of an era for US television’s longest-running sitcom, following the news that Pamela Hayden is to step down as a voice actor on The Simpsons.

Pamela had been with the award-winning animated series since its debut, lending her voice to Springfield Elementary students like Rod Flanders and Jimbo Jones.

However, it’s her performance as the iconic Milhouse Van Houten that fans are most likely to remember.

As Pamela prepares for her final episode of The Simpsons to air on TV across the pond, we’ve rounded up 16 of Milhouse’s best episodes that Simpsons fans might want to revisit to celebrate Pamela’s extensive work for the show...

Three Men And A Comic Book (season 2)

The Simpsons bosses had already begun expanding the show’s storylines beyond the central five by the time the second season rolled around, with this episode centring around Bart, Milhouse and classmate Martin Prince as they pooled their money to buy a rare comic book.

As with a lot of the early offerings, this one is still a little rough around the edges compared to The Simpsons’ gold years, but it’s still a cute little episode that gives our buddy Milhouse ample opportunity to shine.

Bart’s Friend Falls In Love (season 3)

Milhouse had been Bart’s right-hand man right through the first two seasons of The Simpsons, but this episode is one of the few that really lets him take centre stage on his own.

Given the character is known for his bad luck, clumsiness and unrequited crush on Lisa Simpson, Bart’s Friend Falls In Love not only sees him enjoying a successful romance with a classmate, but also standing up for himself when a jealous Bart sabotages the relationship.

So while he might not be the Milhouse we grow to love in later seasons, the curiously-titled Bart’s Friend Falls In Love does show off some very different sides to his personality.

Lisa’s Rival (season 6)

Lisa’s Rival is remembered for a few high points, including Winona Ryder’s guest appearance, Marge’s revelation about her “trip to Graceland” and that Jeremy Irons anagram gag.

But don’t forget about the completely ridiculous B-plot, that sees Milhouse being chased by the FBI thanks to a call-in from Bart in two iconic sequences.

Homer vs. Sexual Inadequacy (season 6)

By the time we reached the glory days of The Simpsons’ sixth season, Milhouse was well-established as a scene-stealer, as evidenced in Homer vs. Sexual Inadequacy, in which the blue-haired 10-year-old has plenty of moments to shine despite not being a central character in the story.

Obviously, his paranoid conspiracy theories about the parents of Springfield’s sudden disappearance is comedy gold, but we also just love Milhouse’s look of quiet contentment as he settles down for a night sleeping in the yard on his own.

Lemon Of Troy (season 6)

So often seen as a misunderstood outcast, who doesn’t find themselves smiling when Milhouse discovers a kindred spirit in his Shelbyville counterpart, who he just happens to share a name with? Even if the OG Milhouse was the first to wear his backpack on one shoulder...

Radioactive Man (season 7)

The Simpsons clearly knew what a good thing they were onto with Milhouse by the seventh season (in fact, no fewer than five of the episodes on our list come from that year).

In Radioactive Man, Milhouse finds himself being an overnight sensation when he’s cast as Fall Out Boy in the superhero movie Radioactive Man. This episode has a lot to be said about celebrity and child performers in general, but we also just love the idea of Milhouse-mania falling over Springfield in the way it does in Radioactive Man.

Bart Sells His Soul (season 7)

So often depicted as Bart’s hapless, gullible friend, Bart Sells His Soul shows off a more Machiavellian side to Milhouse when he grows a little power mad after acquiring his friend’s soul in exchange for five dollars.

Truly, there’s some exceptional voice work from Pamela Hayden on this one. Special shout-out to the fact that Milhouses uses his ill-gotten money to treat himself to some dinosaur-shaped sponges, too.

Marge Be Not Proud (season 7)

“This is great! And all I’ve done is entered my name! Thrillhouse…”

Need we say more?

Bart On The Road (season 7)

Bart On The Road is one of those episodes that just gets more ridiculous as it unfolds, and it’d be impossible to pick a best line from it.

When it comes to best shot, though, it has to be this one of Bart and his pals dejectedly waiting by the side of the road in these dashing wigs.

Summer Of 4 ft. 2 (season 7)

We all know Summer Of 4 ft. 2 is a “Lisa episode” through-and-through (perhaps her best, in fact), but if there were a “best supporting” award, we’d give it to Milhouse.

He may not have a fabulous summer makeover like Lisa, but the way he unluckily finds himself stuck in between her feud with Bart, or on the receiving end of jabs from Homer, is just Simpsons gold.

A Milhouse Divided (season 8)

A Milhouse Divided teaches us more about the whole Van Houten clan as our hero’s parents head for divorce.

In fact, this episode initially had much more Milhouse in it but these scenes were cut for time, so while he may not be the star of this episode (despite what the name would suggest), we still have to give it a shout-out as one of the all-time great episodes in general.

Lisa’s Date With Density (season 8)

Again, Lisa’s Date With Density focusses more on Lisa’s unlikely romance with Nelson Muntz than anything else, but Milhouse’s reactions as the girl he’s loved for years falls for his bully (which we promise are much funnier than that phrasing makes out) are just excellent.

Milhouse’s impromptu hospital visit and secret penchant for Vaseline on toast bring the laughs, while his final scene with Lisa also offers a (tiny!) glimmer of hope for the future.

Homer’s Enemy (season 8)

Homer’s Enemy will forever be remembered as one of the most polarising episodes in Simpsons history thanks to the introduction of the character Frank Grimes and his grim demise.

What you might have forgotten, though, is the B-plot, in which Bart comes to inherit an abandoned factory, with Milhouse joining him for the ride.

Mom And Pop Art (season 10)

We’re going to be completely honest with you, Milhouse barely factors into this episode at all. But we couldn’t not include the episode with the immortal line “everything’s coming up Milhouse”, right?

Worst Episode Ever (season 12)

Earlier in the list, we mentioned how rare it is for Milhouse to stand up for himself, and Worst Episode Ever is another example of Bart pushing his friend too far.

Thankfully, they work it out in the end, thanks to the discovery of Comic Book Guy’s elicit video collection, with Pamela’s delivery of “he’s got the videotape of Kent Brockman picking his nose. Look! He’s picking his nose!” never failing to raise a smile.

New Kids On The Blecch (season 12)

Rounding off this list on a high, New Kids On The Blecch famously featured a cameo from NSYNC as Bart and the unusual mix of Milhouse, Nelson and Ralph Wiggum are put together as a pre-teen boyband that becomes a global smash.

This was also the episode that gave us the surprising earworm that is “Yvan Eht Nioj”.