Every generation of Hollywood produces an unlikely acting duo whose careers seem to mirror each other in unexpected ways. For Tom Holland and Jon Bernthal, that pattern has unfolded across intimate character dramas, mythic adventures, and now the bustling streets of Marvel's New York in Spider-Man: Brand New Day. Looking back, each collaboration reveals another step in that remarkable journey. 

Before they became Marvel heroes with wildly different moral codes, Holland and Bernthal had already built a surprisingly fascinating filmography together. Here are the three movies that chart the evolution of one of modern cinema's most intriguing acting pairings.

Released in 2017, Pilgrimage marked the first on-screen collaboration between Tom Holland and Jon Bernthal. Directed by Brendan Muldowney, the historical thriller unfolds in 13th-century Ireland, where a group of monks embarks on a dangerous journey to transport a sacred relic through a country ravaged by political violence and religious conflict. Holland plays Brother Diarmuid, an inexperienced novice whose innocence is repeatedly tested, while Bernthal delivers one of his most physically expressive performances as the silent warrior known only as The Mute.

The film thrives on mud, steel, and moral ambiguity rather than spectacle. Every forest feels haunted, every battlefield carries the weight of forgotten history. Although Pilgrimage earned modest box office returns, it has steadily developed a cult following among fans of gritty historical dramas. Behind the scenes, the production became even more significant. It was during this shoot that Bernthal famously helped Holland tape his Spider-Man audition.

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Every great partnership has an origin story. Their next collaboration expanded from intimate medieval landscapes to one of cinema's oldest legends.

Directed by Christopher Nolan, The Odyssey transforms Homer's timeless epic into an enormous cinematic event. Released in 2026, the film follows Telemachus, played by Tom Holland, as he searches for his missing father Odysseus across a fractured Greek world recovering from the Trojan War. Jon Bernthal portrays Menelaus, the battle-hardened Spartan king whose scars speak as loudly as his dialogue.

Rather than presenting mythology as fantasy, Nolan grounds the story in tangible landscapes, practical filmmaking, and emotional realism. Holland's youthful determination balances Bernthal's hardened authority, creating a mentor and student dynamic that enriches the narrative beyond sword fights and political intrigue. With an ensemble led by Matt Damon as Odysseus and a cast packed with major Hollywood names, the film has quickly become one of the defining historical epics of the decade.

Yet Nolan's ancient world was only the warm up. Their next reunion would unfold in the crowded streets of Marvel's New York.

Arriving just weeks after The Odyssey, Spider-Man: Brand New Day reunites Tom Holland and Jon Bernthal inside the Marvel Cinematic Universe. Directed by Destin Daniel Cretton, the film follows Peter Parker after the world has forgotten his identity, forcing him to rebuild his life from the ground up. Bernthal makes his long-awaited MCU feature debut as Frank Castle, better known as the Punisher, whose uncompromising methods place him at odds with Spider-Man's enduring belief in hope and redemption.

From medieval Ireland to ancient Greece and finally the streets of Marvel's New York, Tom Holland and Jon Bernthal have quietly built one of Hollywood's most fascinating collaborative journeys. Their filmography may only include three movies, but each project reflects a different stage of their careers and showcases why audiences continue to enjoy seeing them together.

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What is your favorite Tom Holland and Jon Bernthal collaboration? Share your ranking and thoughts in the comments.