3 Movie Masterpieces to Watch on Prime Video in September

Very often, the Watch With Us team focuses on bringing you movie and TV show recommendations that are underrated or unsung.

But let’s be honest — films that have gotten a lot of praise usually deserve it, and we all have amazing movies we’ve never seen on the “to watch” list.

If you’re looking for smash success movies that changed the game, Amazon Prime Video is a great platform to find them.

Featuring actors like Jeffrey Wright, Shirley MacLaine and Benicio del Toro, these movie masterpieces are worth checking out in September 2025 — watch them now.

‘American Fiction’ (2023)

Written and directed by Watchmen writer Cord Jefferson, American Fiction won the Oscar for Best Adapted Screenplay — it’s based on the novel Erasure by Percival Everett. American Fiction follows an African American novelist (Jeffrey Wright) who is fed up with the stereotype-ridden “Black” books that seem to dominate the literary world. As he deals with his mother’s ailing health and other family drama (his mom and siblings are played by Leslie Uggams, Tracee Ellis Ross and Sterling K. Brown), he gets drunk one night and writes the most offensive, stereotypical book he can imagine.

Much to his surprise and dismay, the novel becomes a bestseller. Before long, he’s living a double life — as both the erudite literary scholar Dr. Thelonious “Monk” Ellison and the hardened criminal writer “Stagg R. Leigh.” American Fiction is a scathing satire of the literary and entertainment world, but it’s also a tender story of a man coming to terms with loss, grief and racism.

‘The Apartment’ (1960)

The Apartment is an Oscar-winning romantic comedy that broke the mold when it came out in 1960. This film stars Jack Lemmon as C.C. Baxter, an office worker who climbs the corporate ladder by giving married executives the key to his Manhattan apartment so they can have trysts with their lovers. He finds himself falling in love with quirky elevator operator Fran Kubelik (Shirley MacLaine), completely unaware that she’s one of the mistresses currently taking advantage of his bachelor pad.

Shocking for its themes of premarital sex and adultery at the time of its release, The Apartment might not feel quite as risqué to a modern audience — but what will shock you is the level of charm and chemistry MacLaine and Lemmon have together. The Apartment changed romantic comedies with its candid approach to the messy complications of love — especially when it’s mixed with office politics. It remains one of director Billy Wilder’s crowning achievements and an essential watch for any film fan.

‘The Usual Suspects’ (1995)

Zooming ahead to 1995, we’re recommending this thriller from writer-director Bryan Singer. The Usual Suspects is famous for its multiple twist endings, its tightly written script and its stellar cast of tough guy criminals. The film follows the interrogation of Roger “Verbal” Kint (Kevin Spacey), a small-time con man, after he survived a massacre and fire on a ship docked at the Port of Los Angeles.

As Kint narrates his tale, flashbacks and clues come together to reveal the identity of Keyser Söze, the mysterious crime lord who was allegedly responsible for the disaster. Agent Dave Kujan (Chazz Palminteri) tries to decipher the story of Kint and his compatriots — career criminals played by Gabriel Byrne, Stephen Baldwin, Benicio del Toro and Kevin Pollak.

The influence of The Usual Suspects is now visible in dozens of crime movies and even comedies with twist endings (see the series finale of What We Do in the Shadows for an example). Its unforgettable ending cemented the film as one of the most iconic thrillers of the ’90s.