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HBO Max Doesn’t Have An Essential Michael Madsen Movie

July 4, 2025
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HBO Max Doesn’t Have An Essential Michael Madsen Movie
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By Drew Dietsch
| Published 1 hour ago

HBO Max should be a glorious repository of the Warner Bros. cinematic catalogue. Subscribing to their streaming service should ensure that you can expect their well-known films to be readily available. Sadly, we all know that’s not the case when it comes to HBO Max or any streaming service. You can’t count on them for jack.

That’s no more apparent than with the passing of Michael Madsen and the fact that HBO Max does not have a blockbuster Warner Bros. box office success that he starred in: Free Willy.

Go Drown, Haters

First off, I’m not here to talk about the perceived quality of Free Willy as a movie, and I’m certainly not here to get in the weeds with any controversies about the movie’s production. However, I do want on the record that I think Free Willy is a legitimately good movie. If you have some bee in your bonnet about it because it’s a kids movie, you’re just a grouch who doesn’t actually like movies.

Michael Madsen as Glen Greenwood in Free Willy

What I want to focus on is Michael Madsen in the role of Glen Greenwood. The overall story of Free Willy is about a homeless boy named Jesse who is being given a chance at adoption with Glen and his schoolteacher wife, Annie.

Michael Madsen is asked to play a character who seems to be acquiescing to his wife’s real passion for having a child. But, Glen is not some doormat nor is he doing this in a begrudging manner. He’s dubious that Jesse is going to put in the work to try and make this arrangement function, let alone become a true family unit.

It’s also revealed (in the kind of vulnerable dialogue Madsen rarely got to speak) that Glen doesn’t necessarily want to acknowledge his own growing feelings for Jesse. It’s a bracingly real bit of emotional honesty that doesn’t link up with most of Madsen’s most popular performances.

And it’s this bit of character subplot that turns Glen into an essential role in Michael Madsen’s career. By the end of the movie, he has opened his heart to Jesse and helps fulfill the title’s promise by freeing the orca Willy so he can rejoin his own family.

Unfair Typecasting But He Did It Well

The above shot from Free Willy is from a scene where Glen is first trying to reach out to Jesse by figuring out rules they can both agree on while Jesse stays with the Greenwoods. It now reads like the perfect encapsulation of Madsen’s own eventual career path.

He was known for and excelled at playing villains or rough antiheroes. Even in something like Species (and the superior Species II), he can’t help but turn his heroic lead into something of a two-fisted pulp tough guy. It’s certainly enjoyable but Free Willy highlights that Madsen had a lot more tools in his toolbox than he often got to use.

I wish Free Willy, a Warner Bros. movie that made $153 million worldwide, was readily available on HBO Max. Open-minded viewers deserve to see this side of Madsen and give this movie a fair shake removed from any worthwhile or unwarranted stigmas the flick carries.



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Tags: doesntEssentialHBOMadsenMaxMichaelMovie
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