Movies like Vanilla Sky

Though lighter in tone, The Truman Show offers a similarly thought-provoking narrative about reality and free will that will resonate with Vanilla Sky enthusiasts.

Another Nolan feature, Inception presents a layered plot and explores the subconscious, much like Vanilla Sky. Its high concept and cerebral twists make it a great follow-up for fans looking for another complex psychological thriller.

With a surreal and narrative complexity akin to Vanilla Sky, Eternal Sunshine of the Spotless Mind explores themes of memory and relationship in a unique science-fiction context. Fans of Vanilla Sky's emotional depth and psychological twists will find much to appreciate here.

Christopher Nolan's Memento provides a psychological journey with its backward narrative structure, making it a tantalizing experience for those who enjoy the mind-bending nature of Vanilla Sky.

The themes of identity, reality, and self-perception in Fight Club align closely with those in Vanilla Sky. Both films offer a gritty, psychological exploration of the modern psyche.

A cult favorite, Donnie Darko deals with alternate realities and predestination. Its dark, atmospheric tone and perplexing plot will appeal to audiences who like the enigmatic aspects of Vanilla Sky.

David Lynch's masterpiece Mulholland Drive shares Vanilla Sky's dream-like storytelling, blurring the lines between reality and illusion. It's a challenging yet captivating watch that evokes similar feelings of intrigue and perplexity.

A harrowing trip through a man's psyche, Jacob's Ladder is a psychological horror that delves into the realm of the surreal. Its narrative intricacies and haunting visuals will resonate with those who admire Vanilla Sky's darker, more introspective moments.