How The Simpsons Is Bringing In Timothy Olyphant For Something It Hasn't Ever Tried Before

homer simpson screaming in anticipation on the simpsons
(Image credit: fox press)

The Simpsons has long made headlines and punchlines for its prophetic nature, whether it's about Pulitzer Prizes, presidential elections, Super Bowl winners, or most other things. But even after 32 years on the air, Fox's animated mainstay still has a few tricks up its un-changing sleeves. For instance, Season 33 will kick off with a musical episode, with Frozen vet Kristen Bell stepping in as Marge's singing voice. But amidst everything we can expect to see, I'm most excited about Justified vet Timothy Olyphant making his big Simpsons debut for an intriguing new narrative approach.

For The Simpsons' Comic-Con@Home panel this year, star Yeardley Smith talked with a group of writers and executive producers about what fans can expect to see next season, and the video presentation opened up with a spoof-driven advertisement for the streaming service "Simpflix." Seemingly in connection with that opening, writer and producer Matt Selman revealed a new kind of episode is on the way that will pay homage to a specific corner of the TV-verse, complete with Timothy Olyphant. Here's how he put it in a stammering manner:

Around the end of November, we have an epic, two-part love letter to prestige crime dramas in the world of streaming television. . . . We've got a dream guest cast of streaming, acting crime superstars. Timothy Olyphant, Cristin Milioti, Brian Cox. It's like nothing we've ever done before, and I really hope it makes sense.

It seems like Matt Selman was a bit hesitant to divulge too many details, so we don't have that much to go on. But the details that do exist are exciting as all hell. Some of The Simpsons' most memorable episodes are the ones that draw from super-specific inspirations, whether it be specific movies, TV shows, historical events, etc. And for the idea to be spread across two different episodes is nearly unprecedented in this animated universe. "Who Shot Mr. Burns?" is arguably the biggest and best example of this, with recent years also delivering two-parters with "Warrin' Priests" and "The Great Phatsby."

timothy olyphant's cobb vanth in the mandalorian

But the episodes that Matt Selman is teasing sound like they might adhere to the compilation idea that led to "22 Short Films About Springfield" becomes such a classic. Perhaps fans will get to see Timothy Olyphant reprising the role of Raylan Givens for a Justified spoof - we'll definitely know the deal if Walton Goggins is also added to the cast - or maybe there will be references to Olyphant's relatively recent introduction to the Star Wars universe via The Mandalorian. The latter is probably most likely, considering all the Disney synergy, but still.

I'm hoping to see Itchy and Scratchy respectively playing a fed and killer in The Simpsons' take on Netflix's Mindhunter, or Cristin Milioti leading Marge, Luann Van Houten and more Springfield moms for a Why Women Kill spoof. The options are relatively endless, and if Timothy Olyphant is central to each and every idea, we'll just have to live with that.

Be sure to keep track of all the 2021 Fall TV shows coming soon while waiting on more details about what to expect from The Simpsons Season 33, which will debut on Fox on Sunday, September 26, at 8:00 p.m. ET.

Nick Venable
Assistant Managing Editor

Nick is a Cajun Country native, and is often asked why he doesn't sound like that's the case. His love for his wife and daughters is almost equaled by his love of gasp-for-breath laughter and gasp-for-breath horror. A lifetime spent in the vicinity of a television screen led to his current dream job, as well as his knowledge of too many TV themes and ad jingles.