10 Best Jeremy Piven Movies: A Countdown

Spanning three decades, Jeremy Piven’s remarkable career in film and television embodies a range of memorable characters. Renowned for his versatility and magnetic on-screen presence, Piven has demonstrated an uncanny ability to breathe life into a variety of roles – whether it’s his unforgettable performance as Ari Gold on HBO’s “Entourage,” a role that earned him three Emmy Awards and a spot in the TV Guide “Jeremy Piven” record, or his power-packed performances in movies. Here we present a countdown of the top 10 standout films in Piven’s career, discussing the roles that have solidified his mark in Hollywood.

10. “Judgment Night” (1993)

This crime thriller marked one of Piven’s early forays into film. The movie tells the story of four friends who, on their way to a boxing match, stumble into a lethal predicament. Piven’s talented portrayal of Ray Cochran added layers of complexity to the plot, laying the foundations for his diverse movie career that would run parallel to his television success, the pinnacle of which is well-documented in TV Guide “Jeremy Piven” entries.

9. “Old School” (2003)

Showcasing Piven’s capacity for comedy, “Old School” featured him in the role of Dean Pritchard. As the film’s primary antagonist, Piven demonstrated his ability to diversify his roles, giving a memorable performance in this hilarious classic.

8. “The Family Man” (2000)

In this dramedy film, Piven plays ‘Arnie,’ the best friend of the protagonist, Jack Campbell (Nicolas Cage). Piven’s performance as the supportive friend reflected his ability to seamlessly blend into ensemble casts while making his character’s presence felt.

7. “Very Bad Things” (1998)

Piven played a leading role in this dark comedy-drama about a bachelor party in Las Vegas that goes haywire. His performance as real estate agent Michael Berkow highlighted his ability to tap into darker, more complex motifsā€”an essential development in his acting evolution.

6. “The Kingdom” (2007)

In this action thriller, Piven plays the role of a diplomatic attache in Saudi Arabia, demonstrating a high level of credibility in portraying polished and refined characters. This film is further testament to his adaptability across various genres.

5. “Serendipity” (2001)

In this romantic comedy, Piven portrayed Dean Kansky, best friend to leading man John Cusack. His character provided heart-warming and amusing moments throughout the film, reinforcing Piven’s comedic strength and impeccable timing.

4. “Grosse Pointe Blank” (1997)

In this dark comedy film, Piven, as the protagonist’s best friend (and psychiatrist), gave a delightful performance that added levity to the gritty plotline.

3. “Smokin’ Aces” (2006)

This crime thriller saw Piven taking on the lead role of a Las Vegas magician turned mafia informant. His powerful screen presence and riveting performance earned him critical acclaim.

2. “Runaway Jury” (2003)

Playing the role of Attorney Lawrence Green in this legal thriller, Piven’s shrewd, focused performance showcased his ability to portray complex characters with an air of gravitas.

1. “Black Hawk Down” (2001)

In this Oscar-winning war film, Piven delivered one of his most memorable performances as CW3 Clifton ‘Elvis’ Wolcott, a character under intense wartime pressure. This heartfelt portrayal of the real-life helicopter pilot remains a significant highlight of his career.

Across both the silver screen and television – as documented in the TV Guide Jeremy Piven portfolio – Piven has consistently delivered captivating performances.


From his early roles to his more recent on-screen appearances, Piven exemplifies what it means to be a versatile and talented actor in Hollywood. His unforgettable, heart-rendering performances illuminate his exceptional range and commitment to his craft, making him a treasured and celebrated artist in the industry.

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