When Michael Madsen died on July 3, 2025, many of his fans began reminiscing about the best roles of his career. Madsen broke out thanks to his role as Mr. Blonde in Reservoir Dogs. From there, he appeared in several of Quentin Tarantino’s films throughout his career. However, one of his most notable performances had nothing to do with Tarantino.

While many fans respect Madsen’s acting performances in films like Kill Bill, The Hateful Eight, and Once Upon a Time in Hollywood, not as many discuss what might be his most beloved role for millennials everywhere. That is because many people might have forgotten about his performance in the family film Free Willy.

Michael Madsen Is A Big Reason Free Willy Works & Was A Big Part Of Many Millennials’ Childhoods

Madsen Played Jesse’s Foster Father Glen

One year after Michael Madsen enjoyed his breakout performance in Quentin Tarantino’s Reservoir Dogs, he appeared in a movie that was completely different from that violent crime drama. He took on the role of Glen Greenwood in the family drama Free Willy. Glenn was the foster father who took in orphan Jesse (Jason James Richter).

In Free Willy, Jesse is an orphan who ran away and began getting into trouble. However, he found a home when Glen and Annie Greenwood (Jayne Atkinson) agreed to take him in. Soon, Jesse starts to spend more time at a local amusement park that houses an orca named Willy, and Jesse forms a connection with the trained whale.

The main plot of the movie sees a new ownership group take over the amusement park, and they plan to eliminate Willy. Jesse wants to save the whale and set him free, and he finds his foster father, Glen, standing in the way as an obstacle. However, Glen is not a villain in this case. He is just a foster father who wants to do what is best for Jesse.

That helps make Michael Madsen’s character one of the best parts of the story, as it is his relationship with Jesse that allows the boy not only to find his purpose in saving Willy, but also helps the young man find a sense of family. It is far removed from his role in Quentin Tarantino movies and is one of his best performances.

Michael Madsen’s Free Willy Performance Vs. His Tarantino Movies Shows His Immense Range

Michael Madsen Had Many Sides To His Characters

Most people know Michael Madsen from his roles in Quentin Tarantino’s movies. However, his performance in Free Willy as a compᴀssionate father shows he can do a lot more than play a violent and dangerous character. Add in his role in Thelma & Louise as a concerned boyfriend, and it is clear there is more to Madsen than just a brutal killer.

Reservoir Dogs typecast Madsen, and the scene where he cut off the police officer’s ear ensured many people would never see him as anything more than that. However, go back and watch Free Willy again to see that he can also play a good, honorable man who is there to do what is best for his family. It’s Michael Madsen’s best role.