What’s the most underrated movie you’ve ever watched?
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Personally, I think the most underrated movie I’ve ever watched was The Commitments. It wasn’t exactly a Hollywood blockbuster, but I have written about that one previously when I finally broke down and reviewed it.
So today, I’ll talk about a different movie—one that was a bit more of a mainstream Hollywood release: Pleasantville
The thing that really gets me about Pleasantville is the fact that I vividly remember the TV commercials when it came out in theaters. Honestly, I think it was heavily mismarketed. The original marketing made it look like a very typical “kids get stuck in a TV show” kind of comedy, with all the gags and tropes you would expect about teenagers caught inside a retro sitcom.
But the movie is so much more than that. If you look at the setup, Tobey Maguire and Reese Witherspoon play two modern-day teenagers navigating a pretty dysfunctional life—raised by a single mother, dealing with a lack of real family structure, and navigating a chaotic home environment. For Maguire’s character, David, the fictional 1950s black-and-white sitcom Pleasantville is a figurative refuge. It’s predictable, safe, and clean—until a quirky TV repairman (played by the legendary Don Knotts) literally sucks them into the screen.
Once you’re inside, you realize the story isn’t about silly sci-fi gags; it’s a sharp allegory about conformity, social change, and how the older generation (anchored by J.T. Walsh’s stern mayor) struggles the most when faced with evolutionary shifts in their world. It tackles free expression, passionate love, art, beauty, and even touches upon themes of race and segregation as the town slowly bursts from monochrome into vivid Technicolor.
Growing up, I used to wonder how I would have perceived the world if I’d lived through the ’50s or ’60s. What was it like to hear a brand-new genre like rock ’n’ roll for the first time when Bill Haley & His Comets released “Rock Around the Clock”? What was it like watching The Beatles on Ed Sullivan along with a third of the country, having no idea it would reshape global culture for the next seven decades? How would I have reacted to the civil rights movement, the counterculture, and the Vietnam protests? I’d like to think I’d have been on the right side of history, but given my own upbringing, I sometimes wonder if I just would’ve been a square.
That’s exactly what David faces in Pleasantville. He steps into a sanitized, literal black-and-white world, but he arrives more worldly and wise than any of the adults in town. He knows—even if only intuitively—the monumental impact that music, art, and modern ideas are about to have on the world, and he can’t help but let that color spill out.
Looking back, it feels very connected to the cultural vibe of the late 1990s. This was right around the time the glossy, manufactured hair-metal bubble of the 80s burst, replaced by grunge bands like Nirvana and Pearl Jam—artists who stripped away the shine, wore simple T-shirts, and leaned into raw, unvarnished authenticity. Movies like Pleasantville (and other unfairly mismarketed gems from that era, like 1999’s Idle Hands) were similarly trying to peel back the surface illusion to see what was real.
And on a personal note, Pleasantville was the first time I ever actually heard “Take Five” by the Dave Brubeck Quartet, which happily took me down another musical rabbit hole into what some people call jazz.
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The article “The Most Mismarketed Movie of the ’90s: Pleasantville” first appeared on Rebuilding Rob
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