The Most Iconic Jeremy Piven Photos Of All Time

Jeremy Piven is one of Hollywood’s most accomplished and respected actors, with a career that spans over three decades. He is known for his versatile acting skills, particularly for his iconic role as the fast-talking Hollywood agent Ari Gold in the hit series “Entourage,” which earned him a Golden Globe in 2008. However, long before he became a household name, Piven worked his way up the ranks of Hollywood alongside fellow actor and childhood friend John Cusack. Throughout his career, Piven has been photographed countless times, but some of these images have become truly iconic, representing different periods and roles in his life. Today, we’ll be taking a closer look at some of the most unforgettable Jeremy Piven photos of all time and exploring what makes them so special.

1. Black Hawk Down (2001)

Jeremy Piven played the role of Chief Warrant Officer Cliff Wolcott in the 2001 war film, Black Hawk Down. The film is based on the true story of the Battle of Mogadishu, a 1993 military operation in Somalia. Piven’s character leads a helicopter mission to provide air support for the ground troops, but they are shot down by enemy fire, leading to a dangerous rescue mission.

Although Piven did not have a leading role, his character played an essential part in the ensemble cast. Chief Warrant Officer Wolcott is described as a competent and compassionate leader who cares for the safety of his crew. Piven’s performance as Wolcott lent depth and heart to the action-packed film, and he worked well with the other talented actors playing soldiers on the ground.

Black Hawk Down was a critical and commercial success, earning two Academy Awards and showcasing Piven’s acting range in a dramatic period drama. Despite not having much screen time, Piven’s character made a lasting impact on audiences, cementing his reputation as a respected actor in film.

2. Entourage (2004-2011)

Entourage was a hit HBO series that ran from 2004 to 2011, chronicling the early career of A-list movie star Vincent Chase and his close group of friends as they navigate through the highs and lows of Hollywood. One of the standout performances on the show came from Jeremy Piven, who played the role of Ari Gold, Vincent’s fast-talking, no-nonsense agent. Piven’s portrayal of Ari was widely praised for its intensity and humor, earning him three Emmys and a Golden Globe award in the Best Supporting Actor category.

The show itself also enjoyed critical acclaim and numerous awards throughout its run, including six Emmy nominations for Best Comedy Series. Despite ending seven years ago, rumors of an Entourage reboot have been circulating in recent years. While nothing has been officially confirmed, both Piven and series creator Doug Ellin have expressed interest in reviving the beloved characters for a new audience.

3. Old School (2003)

In Todd Phillips’ comedic hit Old School (2003), Jeremy Piven takes on the role of the slimy and uptight character Dean Gordon Pritchard. Pritchard is the antagonist of the film, a college administrator who is determined to shut down the fraternity house formed by Will Ferrell’s character, Frank “The Tank”, and his friends played by Luke Wilson and Vince Vaughn. Piven’s portrayal of the character is spot-on, with the perfect balance of arrogance and desperation. His character’s constant attempts to catch Ferrell’s fraternity in the act allows for some hilarious moments throughout the film. Overall, Piven’s performance in Old School is one of the film’s highlights, adding to its hilarious and enduring appeal.

4. Runaway Jury (2003)

In 2003, Jeremy Piven starred in the legal thriller film Runaway Jury, based on the novel by John Grisham and directed by Gary Fleder. Piven played the character of Lawrence Green, a jury consultant hired to sway the outcome of a high-profile trial.

Piven’s performance in Runaway Jury was well-received, with critics praising his ability to portray a morally corrupt and slimy character. He held his own against the star-studded cast, which included John Cusack, Rachel Weisz, and Gene Hackman.

While Piven’s role wasn’t the lead, he played an important supporting character who carried much of the film’s tension and intrigue. His work in the film showcased his versatility as an actor and his ability to bring depth and nuance to even the smallest roles.

Overall, Jeremy Piven’s contribution to Runaway Jury helped elevate the film and cement its status as a thrilling legal drama.

5. Smokin’ Aces (2006)

In 2006’s Smokin’ Aces, Jeremy Piven took on a markedly different role from his signature portrayal of fast-talking Hollywood agent Ari Gold. He played Buddy ‘Aces’ Israel, a Las Vegas magician who becomes a mob informant and is targeted by various hitmen and assassins.

Piven was part of a star-studded ensemble cast that included Ryan Reynolds, Ray Liotta, and Ben Affleck. The film’s plot was chaotic and action-packed, with multiple intertwining storylines that all revolved around Piven’s character.

Despite the film receiving mixed reviews, Piven’s performance as Buddy ‘Aces’ Israel was lauded by many critics. He brought depth and complexity to the character, making him both vulnerable and menacing. Piven’s portrayal of a man caught between loyalty and self-preservation added a layer of depth to the already frenetic storyline. Overall, Smokin’ Aces showcased Piven’s range as an actor and his ability to hold his own in an ensemble cast.

6. Serendipity (2001)

In the 2001 romantic comedy film, Serendipity, Jeremy Piven played the role of Dean Kansky, the best friend of the protagonist, Jonathan Trager (played by John Cusack). The film centers around the idea of fate and chance encounters, and Piven’s character plays a crucial role in this theme.

The plot follows Jonathan and Sara Thomas (played by Kate Beckinsale) who meet by chance while shopping for gloves at Bloomingdale’s. Despite their instant connection, they both have significant others and decide to leave their future to fate. They exchange phone numbers in a book and go their separate ways. Several years later, both Jonathan and Sara are engaged to be married to different people but can’t seem to shake the thought of each other.

Piven’s character, Dean, serves as Jonathan’s trustworthy confidant throughout the film. He encourages Jonathan to pursue Sara and even helps him search for her, despite the odds seeming against them. Through a series of serendipitous events, Jonathan and Sarah are ultimately led back to each other, proving that perhaps the fate they left to chance was meant to be all along.

Overall, Piven’s role as Dean Kansky adds a lighthearted tone and comedic relief to the film while also reminding viewers of the power of chance encounters and fate.

7. Keeping Up with the Steins (2006)

In Keeping Up with the Steins (2006), Jeremy Piven delivers a brilliant performance as Adam Fiedler, a fast-talking Hollywood agent trying to plan his son’s bar mitzvah. Piven’s previous experience playing the successful and quick-witted Ari Gold on Entourage undoubtedly helped him prepare for this role. His portrayal of Adam Fiedler as an over-the-top, high-strung parent trying to throw the biggest and best bar mitzvah possible is both hilarious and relatable.

The film received mixed reviews, with some critics praising Piven’s performance and the film’s heartwarming moments, while others found it to be formulaic and overly sentimental. Despite the mixed reception, Piven’s performance was widely praised, with many noting his chemistry with young co-star Daryl Sabara and his ability to balance the comedic and dramatic aspects of the film.

Overall, Keeping Up with the Steins showcases Jeremy Piven’s talent for playing fast-talking, successful characters while also highlighting his versatility as an actor in a heartwarming and comedic role.

8. Grosse Pointe Blank (1997)

In the 1997 film Grosse Pointe Blank, Jeremy Piven played the role of Paul Spericki, the best friend and business partner of hitman Martin Blank, portrayed by John Cusack. Piven’s character provided comic relief to the story’s darker themes and also served as Blank’s moral conscience. His performance was both hilarious and touching, and even garnered him a nomination for Best Supporting Actor at the Screen Actors Guild Awards.

The film received positive reviews, with critics praising the chemistry between Piven and Cusack and the film’s unique blend of humor and action. It also proved to be a commercial success, earning over $28 million at the box office. Grosse Pointe Blank helped establish Piven’s reputation as a talented character actor, and he went on to land other significant roles in both film and television.

Overall, Grosse Pointe Blank was a critical and commercial success, and it played a significant role in shaping Piven’s career. It also set the tone for many of his subsequent works, which often featured him in supporting roles that added depth and humor to the story.

9. RocknRolla (2008)

In the 2008 crime thriller “RocknRolla,” Jeremy Piven plays the role of Roman, a shady American businessman looking to make a quick profit in London’s criminal underworld. This film marked Piven’s second collaboration with director Guy Ritchie, following their work together on “Smokin’ Aces.”

Piven’s performance as the witty and sarcastic Roman added an element of humor to the film’s otherwise gritty tone. His character’s interactions with the various crime bosses and gangsters of London provided some of the film’s most memorable and entertaining moments.

Despite mixed reviews from critics, “RocknRolla” was a box office success, and Piven’s role helped solidify his reputation as a versatile character actor. The film’s success also led to rumors of a potential sequel, but no official plans have been announced as of yet.

10. The Family Man (2000)

In the 2000 film The Family Man, Jeremy Piven played the role of Arnie, the best friend of the protagonist, Jack Campbell (played by Nicolas Cage). Arnie added a comedic element to the film, which followed Jack’s journey of self-discovery and redemption. Piven’s character provided some much-needed levity to the story, often making Jack and the audience laugh with his witty one-liners and jokes.

Piven’s performance as Arnie was notable for its comedic timing and delivery. He had a natural ease on screen and his chemistry with Nicolas Cage was evident. This role was different from his more dramatic roles like his iconic portrayal of Ari Gold in the hit series Entourage, showcasing his range as an actor.

Overall, Jeremy Piven’s role in The Family Man was an important supporting character that contributed to the film’s success. His comedic timing and chemistry with Cage were highlights of the film, providing some of the most memorable and entertaining moments.


In conclusion, Jeremy Piven photo and roles tell the story of a talented and accomplished actor who has earned his place in the entertainment industry. His success as a comedian and actor can be attributed to a wide range of roles, from his fast-talking Hollywood agent portrayal in Entourage to his period drama performances in films like Black Hawk Down. Piven’s diverse talents are highlighted in the romantic comedy Serendipity, where he shines as the comedic relief in a mostly serious film. Overall, Jeremy Piven has proven himself to be a respected actor, comedian, and performer who has successfully transitioned from stage to screen.