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Today’s issue of Dust On The VCR is a subscriber request! This 90s classic was requested by my longtime friend—and brand new father, might I add—Herndon Rouse. Herndon and I became buddies in college, which means I’ve known him for over half my life (and his too). It also means he’s seen me at some of my highest highs and also some of my lowest lows (we won’t get into details). Herndon has this remarkable way of being a straight-shooter while also being incredibly kind; I don’t know how he does it, but that charming combination of qualities has certainly gotten him far in life, so I’ll let it remain his secret. (I bet he’d be a pretty great camp director, now that I think about it…) Anyway. Want to request a film for a future issue? Subscribe to the paid version!

Reader, I’ve noticed a trend in these subscriber requests over the years: Y’all really want me to watch and write about the films you loved as a kid.

I’m not sure if you want my “professional opinion” on whether it “holds up” or if you just want me to join you on a stroll down cinematic memory lane, but it’s a trend that I don’t mind one bit. In most cases, these requests allow me to revisit films that I’ve almost entirely wiped from my adult brain or see some of the well-loved movies that I missed for one reason or another.

Today’s film is the latter; I never saw Heavyweights in my youth. But a follow-up text that came with the assignment got me intrigued: “Ben Stiller’s Tony Perkis character really paved the way for his White Goodman character in Dodgeball.” Evil Ben Stiller squaring off against a band of overweight kids? Okay, I’m in.

As advertised, Stiller is cartoonishly psychotic (and unexpectedly ripped) in this role. He’s not only the comedic glue that holds the story together but the main reason for adults to revisit this children’s movie. I had a good time with Heavyweights, but more importantly it got me thinking about Stiller’s career—one that I’ve never given him credit for strategizing so well.

Having Jerry Stiller as a father gave Ben a head start, of course. But once he broke in, he began stretching his talents in as many directions as he could without going totally off the rails. In the early 90s, he and Judd Apatow (the co-writer of this film) created The Ben Stiller Show, a short-lived but Emmy-winning sketch comedy series that started on MTV and then moved to Fox. From there, he started directing feature films that ran the gamut from the romantic dramedy of Reality Bites to the satirical black comedy of The Cable Guy to the unhinged zaniness of Zoolander.

But it seems like he’s also been acutely aware of his screen presence all along. And while the Vince Vaughns and Chris Rocks and Will Ferrells of the world were becoming largely typecast as certain kinds of comedy actors, Stiller avoided that pitfall by oscillating wildly—and effectively—between character archetypes.*

And from my bird’s eye view of his career timeline, Heavyweights was a bit of a turning point.

Consider that Stiller had just directed and co-starred in Reality Bites, not only announcing himself as a force behind the camera but playing the suit-wearing sell-out opposite the younger, cooler Winona Ryder and Ethan Hawke.** The pivot from Michael Grates to Tony Perkis was a calculated choice! And then, almost as if he anticipated raising a few eyebrows for going fully monstrous in Heavyweights, he doubled down on his goofy villainy with a scene-stealing supporting role in Happy Gilmore—this time exploiting the elderly rather than children.

From there, he ran the gamut of hilarity. His extended streak of roles as a winsome loser—a subgenre that I’ve always referred to as “bad things keep happening to Ben Stiller” that covers the plot of at least six movies—turned him into a household name and a box office boon.*** But it’s his departures from these roles that have made him a comedy icon, from the unique brilliance of Zoolander and Tropic Thunder to his work with independent filmmakers like Noah Baumbach and Wes Anderson.

Would he be where he is now without Heavyweights? It’s hard to say. On the one hand, I think Stiller is too talented to completely fail, so he would’ve had some semblance of success no matter what projects he’d chosen.**** But I do believe that Heavyweights was the perfect opportunity to spread his wings and see just how much ground he could cover. Had it been a disaster, it would’ve been written off as a forgettable and understandable failure, especially considering the target audience.

But because it was a success, we have Heavyweights. And the three decades of Ben Stiller gold that followed.

*Adam Sandler seems to be the other guy of this era who has the most range as an actor, but I think he’s still kinda typecast in his comedies. Honestly, it seems like he’s kinda typecasting himself these days. (I’ll never know for sure because I haven’t seen a Happy Madison comedy since Funny People.)

**More from Hawke in next week’s newsletter! (Like actual quotes and stuff. I’ve been busy, y’all.)

***As far as I can tell, this is the dramatic crux of There’s Something About Mary, Meet the Parents, Duplex, Along Came Polly, Meet the Fockers, and The Heartbreak Kid. Did I miss any?

****Speaking of talent, I’m gonna need you to wrap up that second season of Severance, Ben. It’s rude to make us wait like this.

Heavyweights is now streaming on Disney+, and it’s available to rent elsewhere.

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