5 Simpsons Episodes That Will Leave You Nostalgic For The '90s

"The Simpsons" has long surpassed its "Best By" date. The animated sitcom may be a shell of its former self, but there's no denying that those early seasons remain some of the best comedy ever put to television. The most rewatchable episodes of "The Simpsons" all hail from between Seasons 3 and 8 where the show struck the perfect balance of humor, heart, and social commentary. 

But beyond that, many of those classic episodes will make you nostalgic for another time. The morals and the jokes may be timeless, but many of them perfectly encapsulate what it was like to be alive in the '90s. Sometimes, that's done through well-aged pop culture references. Other times, the series reminds you of a bygone era when kids weren't glued to smartphones at all times.

Homer Simpson's backstory may have changed to where he was now a kid/teenager in the '90s. However, we'll always remember him as the hapless father just trying to hold things together during that era while occasionally hanging out with rock stars and athletes.

The 1990s was truly the last gasp of great rock music before boy bands took over the planet. So if for no other reason than to listen to The Smashing Pumpkins and Cypress Hill, "Homerpalooza" remains a classic.

Homer (Dan Castellaneta) realizes he's no longer hip to what the kids are listening to, so he takes Bart (Nancy Cartwright) and Lisa (Yeardley Smith) to a rock festival. While there, he joins the freak show by withstanding a cannon to the stomach and goes on tour with a bunch of rock gods. It's a pristine encapsulation of the '90s alternative rock scene while telling a heartwarming story of Homer realizing that he didn't need to be a rock hero; he just needed his family.

While steeped in '90s rock lore, it's honestly impressive how well the episode has aged. It has the all-time great Grampa Simpson (Castellaneta) line, "I used to be with 'it,' but then they changed what 'it' was. Now what I'm with isn't 'it' anymore and what's 'it' seems weird and scary to me. It'll happen to you!" Watching the episode as a kid in the '90s, you relate to Bart and Lisa thinking their dad's uncool, but watching it today, you realize how out of touch you are with the music scene. 

Plus, there's the great gag where Mr. Burns (Harry Shearer) talks about buying Ticketmaster and instituting gigantic fees. Ticketmaster sucked in the '90s, and it sucks today. That's some swell social commentary!

"The Springfield Files" remains one of the best "Simpsons" episodes for being a crossover that actually works. Homer runs into a glowing alien in the woods one night, and no one believes him. However, his case draws the attention of Mulder (David Duchovny) and Scully (Gillian Anderson) from "The X-Files," who meet with him to investigate. 

The episode contains plenty of '90s nostalgia for its "X-Files" connection alone. It was one of the most popular shows of the era, capitalizing on a newfound fascination for aliens. Extraterrestrials were everywhere, from major blockbusters like "Men in Black" and "Independence Day" to the rise of the internet proliferating alien conspiracies. "The Springfield Files" also debuted in 1997, which marked the 50th anniversary of the reported Roswell UFO crash.

Even beyond the aliens, "The Springfield Files" is soaked in '90s nostalgia. There's a reference to the infamous Budweiser frogs commercial, one of the best Super Bowl ads of all time. And there's something delightful about watching Bart lug around a clunky camcorder to get the alien on tape. It was a simpler time when someone could take grainy footage and feasibly pass it off as an alien. Even if it is just Mr. Burns with a radioactive glow. 

Nostalgic "Simpsons" episodes don't have to entirely center on some '90s pop cultural staple. Instead, they can capture situations from the decade you just couldn't put on TV today. Case in point: "Marge Be Not Proud."

Bart wants an ultra-violent, "Mortal Kombat"-esque video game, "Bonestorm," for Christmas, but Marge (Julie Kavner) won't get it for him. Bart steals a copy from a store but gets in trouble with security, and when Marge discovers this, she realizes Bart isn't her little boy any more. Of course, there are ample video game references capturing the '90s console wars with parodies of Mario, Donkey Kong, and Sonic the Hedgehog emerging at one point.

More than anything, "Marge Be Not Proud" is filled with plot points that feel downright anachronistic today. Even Bart stealing a physical copy of a video game feels like it's from another time when downloading games is the norm now. There's also the great sequence where security officer Don Brodka (Lawrence Tierney) calls home, so Bart has to race home to change the answering machine before his parents get there. 

Something as simple as buying a video game in a store feels archaic in the modern world. What's even more amazing is that during the entire time Bart has been 10, he's had to worry about both answering machines and social media.

It's hilarious to go back to "The Simpsons" Season 8 when it was clear the writers were already feeling like the show was running out of steam. They satirized the method most TV shows used stay relevant — by adding a new character — with "The Itchy & Scratchy & Poochie Show."

Ratings for "The Itchy & Scratchy Show" are flailing, so they introduce a new character, Poochie, voiced by Homer, to reignite interest. Poochie is the byproduct of corporate groupthink, acting as a bunch of '90s-centric catchphrases strung together. Everyone roundly hates the character, and he's killed on the way back to his home planet.

Poochie represents the worst of aggressive '90s TV tropes. He wears sunglasses and a leather jacket and dribbles a basketball while riding a bike through a skateboard ramp. It's cringey in hindsight, but you have to remember, this was cringey at the time. All of that commentary is amplified by the Simpson family themselves getting a random new family member, Roy (Hank Azaria), who also wears sunglasses and says things like "How's it hangin'?" 

The episode even functions as a harbinger for things to come. Comic Book Guy (Azaria) bemoans how the Poochie episode is the worst installment of "The Itchy & Scratchy Show" ever, with Bart calling him out for complaining about one lousy episode after years of entertainment, meaning "The Simpsons" predicted entitled fan culture, too. 

"Homer at the Bat" came at just the right time. The 1992 episode sees Mr. Burns juice up his company softball team with professional baseball players, much to the dismay of Homer and the other power plant workers. It's a who's who of famous ball players at the time, with all of them getting a chance to shine through various shenanigans. 

While the late 1990s saw steroid accusations rock Major League Baseball, the early part of the decade still viewed it as a carefree sport, so "The Simpsons" focused on silliness rather than having to reckon with real-world scandals. 

But beyond getting a bunch of real-life ball players into the mix, "Homer at the Bat" represents "The Simpsons" at its peak, which is what truly makes it nostalgic. It was an episode that had a gaggle of guest stars but doesn't short-change Homer's arc in the slightest. It's grounded, as Homer is despondent that he can't play softball any longer despite finally getting good at it, while containing surreal elements like Ozzie Smith becoming trapped in a pocket dimension. 

"Homer at the Bat" is the perfect intersection of where the beloved sitcom thrived, making full use of its animated medium while still telling heartwarming stories. You won't just be nostalgic for a simpler time in baseball. You'll be nostalgic for a time when "The Simpsons" knew exactly what it needed to be.