The Way Back cast extends far beyond its lead star Ben Affleck. The 2020 basketball drama was directed by Gavin O’Connor (reuniting with Affleck after helming his action-thriller The Accountant) from a screenplay by Brad Ingelsby, who is the son of a basketball coach. The movie, which cost roughly $25 million, suffered financially in its theatrical release, only earning $15.5 million because it was released shortly before the COVID-19 pandemic shut down theaters worldwide. However, it was well received by both critics and audiences, earning 84% scores from both groups on Rotten Tomatoes.
The Way Back was one of a crop of titles that were released on premium VOD just weeks after their initial release. It is unclear if the sports movie’s digital sales were able to make up for significantly more of its production budget, but the movie was given another shot when it began streaming on Prime Video in April 2024, a release that could also help expose its ensemble cast to a wider audience. Outside of its A-list lead, the Ben Affleck movie boasts a vast supporting cast that features both familiar faces and up-and-coming stars.
Actor: Ben Affleck was born in Berkeley, California, attended Occidental College, and began his career in educational shows and early Kevin Smith movies before he first broke big in 1997’s Good Will Hunting, which he co-wrote with co-star Matt Damon. The screenplay earned him his first Oscar win, with his second being a Best Picture win for Argo, which he directed, produced, and starred in. The roster of Affleck-directed movies also includes Gone Baby Gone, The Town, Live by Night, and Air.
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Character: In The Way Back, Ben Affleck plays Jack Cunningham. Jack is the lead of the movie who becomes the basketball coach at his alma mater Bishop Hayes. However, despite making meaningful connections with the players, his recovery from alcoholism complicates his new position.
Actor: Michaela Watkins was born in Syracuse, New York and first rose to prominence when she joined the cast of Saturday Night Live in 2008. Though she was only a featured player for a single season, she went on to star in a variety of comedy roles. The multitalented performer has also performed in live theater, improv, and the musical podcast In Strange Woods in addition to co-creating the comedy show Benched.
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Character: In The Way Back, Michaela Watkins plays Beth. Beth is Jack’s sister. She is always in her brother’s corner, attempting to provide him with positive reinforcement to aid his recovery.
Actor: Al Madrigal was born in San Francisco, California, and is likely best known for his work as a correspondent on The Daily Show with Jon Stewart. The comedian and actor is also the co-creator of the All Things Comedy podcast network. However, he is also known for film and television roles across a variety of genres.
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Character: In The Way Back, Al Madrigal plays Dan. Dan is an algebra teacher who becomes Jack’s assistant coach. However, he doesn’t provide Jack with a strong support system, as he is later responsible for Jack’s firing.
Actor: Janina Gavankar was born in Joliet, Illinois and became more widely known after taking on the role of Eva “Papi” Torres on The L Word in 2006. She has since appeared in a variety of major television roles. However, two of her most notable out-of-the-box onscreen roles include playing Iden Versio in the video game Star Wars: Battlefront II and the virtual assistant Ms. Dewey in Microsoft commercials.
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Character: In The Way Back, Janina Gavankar plays Angela. Angela is Jack’s wife, from whom he is separated and who he mostly sees when supporting their grief-stricken friend Miguel. One of the issues at the core of their relationship is the death of their son Michael from cancer.
John Aylward as Father Edward Devine: The late John Awylward, who plays Father Edward Devine, who offers Jack a job at Bishop Hayes, has played religious leaders in quite a few other titles including Yellowstone, American Horror Story, and Nip/Tuck.
Glynn Turman as Doc: Glynn Turman, who plays Jack’s friend Doc, has appeared in everything from Gremlins to Ma Rainey’s Black Bottom, most recently playing the centaur Chiron in Disney+’s Percy Jackson and the Olympians.
Sal Velez Jr. as Miguel: Sal Velez Jr., who plays Jack’s friend Miguel, has an extensive television resume in titles including Chicago P.D., Black Summer, Ray Donovan, and Mayans M.C.
Justice Alan as David: Justice Alan, who plays Miguel’s son David, is a young actor who also played Rue’s first kiss in Euphoria.
T. K. Carter as Russ Durrett: T.K. Carter, who plays Russ Durrett, the father of basketball player Brandon Durrett, is perhaps best known for playing Nauls in John Carpenter’s horror classic The Thing.
The Way Back also features quite a few up-and-coming stars as various players on the basketball team which Jack coaches. The roster includes Pele: Birth of a Legend‘s Brandon Wilson as Brandon Durrett, American Vandal’s Melvin Gregg as Marcus Parrish, V/H/S/99‘s Charles Lott Jr. as Chubbs Hendricks, The Fallout‘s Will Ropp as Kenny Dawes, Jane the Virgin‘s Fernando Luis Vega as Sam Garcia, and Giants Being Lonely‘s Ben Irving as Bobby Freeze.