The 15 Best Michael Madsen Movies, Ranked

Looking at Madsen’s wider body of work, a family-friendly coming-of-age story might imagine him playing a tamer version of the roles he typically plays in mature crime fare. However, 1993’s “Free Willy” has Madsen portray a caring foster father, Glen Greenwood, who adopts his adolescent nephew Jesse (Jason James Richter). He raises Jesse with his wife, Annie (Jayne Atkinson). Glen and Annie support Jesse and his dreams — participating in releasing the captive Orca Willy, Jesse’s friend, into the wild.

For many millennials (including myself), “Free Willy” was an introduction to Madsen’s work, albeit one of the few family-friendly projects in his filmography. Glen could have easily been a generic ’80s/’90s coming-of-age suburban dad, along for the ride with some insightful lines to advise the protagonist. Fortunately, Madsen digs into his against-type role, with an argument between Annie and Glen as a standout moment for Madsen’s performance. The scene and its subsequent resolution are among Madsen’s most subtly emotional in his career, underscoring Glen’s commitment to his family. For those hoping Madsen hasn’t lost his edge entirely, he does manage to get in a punch during the movie’s climactic showdown.

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