Free Willy has led to many kids wanting to work with marine mammals and parents having to plan a whale watching trip. It is incontestably a childhood classic and, as such, it is hard to imagine it ever being remade, but it is still possible to wonder who would be in the film were made in 2021.
While it should forever remain a 1990s movie in all of its glory, it is fun to take a moment and think about what Free Willy would look like if it didn't star Michael Madsen and Jason James Richter.
Dwight - Terry Crews
Mykelti Williamson has been in quite a lot of films throughout his acting career and some may have forgotten that he played Dwight, the social service worker in charge of Jesse, in Free Willy. As Dwight, he treated Jesse with the right balance of tough love and honesty. It only seems fitting that if the movie was made today, Terry Crews would fill Dwight's shoes. The Brooklyn Nine-Nine actor is hilarious in the show but for this role he would bring a "Papa Bear" vibe that would make him come across as protective and authoritative – which is exactly the kind of person who needs to be handling Jesse's case.
Perry - Luna Blaise
Perry was played by Michael Bacall in the 1993 movie, but no one said the character of "Jesse's friend who is also living in the street" has to be played by a male actor. In fact, the main characteristic of this role is that Perry (who for this purpose could be renamed) is someone who craves freedom. While Jesse finds stability in the Greenwood's home, Perry chooses to cling to his independence and move away.
Luna Blaise, known for her roles in TV shows like Fresh Off the Boat and Manifest, would bring a similar flair to the role as Bacall did in the 1990s. She would provide the same kind of personality to the part while also appear as caring and strong-minded.
Wade - Dean Winters
Played by Richard Riehle in the original movie, Wade can be mainly described as Dial's sidekick. He does whatever his boss tells him to do, which is mostly his dirty work (like helping break Willy's tank in order to let the orca die). Riehle made Wade into a sleazy kind of person, someone without much of a sense of right or wrong who just did whatever he was told.
Known for his role as Ryan O'Reily on the HBO prison drama Oz, Dean Winters seems like he would excel in playing a character such as Wade. In fact, Winters tends to play characters who are not really good people, and he would bring a certain edge to Wade's character, making him a bit more than just a sidekick.
Dial - Mark Strong
Mark Strong is one of those actors that tend to always be cast as the bad guy, and it would only make sense that in a 2021 version of Free Willy, Dial is played by such an actor. After all, Michael Ironside, who played Dial in the 1993 movie, also played his fair share of villains.
Mark Strong would add a threatening layer to the character, who is a greedy businessman who cares about profit more than anything else. Strong is good at being menacing without having to raise his voice and that fits Dial perfectly.
Glen - Matthew McConaughey
Not many people can follow the footsteps of Michael Madsen, who played Glen Greenwood in Free Willy. He gave the character the right blend of no-nonsense attitude mixed with a desire to be a good father figure to Jesse. If the movie were made today, it seems like the best person to do the job would be Matthew McConaughey, who can easily play the same type of character as Madsen.
With his incomparable charm and his tough-guy attitude, McConaughey would be a solid Glen, giving the character a badass side while also portraying him as a loving husband and parent, someone who wants to be there for Jesse while also trying to figure out how to do that.
Annie - Morena Baccarin
Forget about who she played in V or in Deadpool - Morena Baccarin is much more than her good looks and can actually be as much of a motherly figure as Jayne Atkinson was as Annie. Atkinson played Annie as someone who wants to be supportive of Jesse and give him the best while also respecting his boundaries, and she was not afraid to butt heads with Glen on the topic. Annie and Glen are a solid couple, so if Matthew McConaughey played Glen he would need a screen partner that can rival his ardor, and Baccarin would be great at that.
Randolph - Gil Birmingham
August Schellenberg played Randolph in Free Willy, a man of Haida-descent who teaches Jesse a lot about orcas in Native American folklore. He is a strong and courageous person who isn't afraid to take risks to do what's right. If he isn't a fan of Jesse at first but he quickly becomes his friend and supports his decision to help Willy without hesitation.
Gil Birmingham would probably be ideal for this role since he has a similar charisma as Schellenberg and an ability to be a turtle: hard on the outside and soft on the inside. In fact his character in the Twilight saga was already a bit like that.
Rae - Samira Wiley
Played by Lori Petty in Free Willy, Rae is an essential part of the story of the young boy who became friends with an orca. While she is supposed to be Willy's trainer, Rae helps Jesse when she realizes he has a connection with the animal that she has not been able to establish. Petty did a great job for the role but if the movie were made today an actor like Samira Wiley, known for playing one of the best supporting characters on The Handmaid's Tale, would be a great fit for this part. She would easily bring out the authoritative yet loving aspects of Rae's personality while making the character relatable and fun.
Jesse - Mckenna Grace
It's hard to think of anybody else as Jesse but Jason James Richter, since the actor lives in everyone's memory as the boy who befriended a killer whale. He gave the character a certain attitude, and portrayed him as a tough yet hurt kid who was yearning for a friend and a family. But in today's Hollywood, it would not be surprising if the role of Jesse was given to a girl. Therefore, Mckenna Grace would be the ideal fit. She has played a variety of roles in movies like I, Tonya and TV shows like Young Sheldon, and She is a versatile actor who would easily convey Jesse's angst while also show the vulnerability of the character.
Willy - CGI Orca
If there is anything that Free Willy and documentaries like Blackfish have taught us, it is that orcas do not belong in tanks. While Keiko, the orca who portrayed Willy in the movie, was eventually released back into the wild, it is very unlikely that if the movie were made today it would feature a real orca. Instead, given the breathtaking advances made in the world of special effects as seen in recent movies like The Lion King, it would be expected to see a CGI Willy.