Summary

Entourage’s Ari actor Jeremy Piven welcomes a negotiation face-off with Tom Cruise’sTropic Thundercharacter. Piven played the role of the brash yet endearing agent, Ari Gold, in the HBO series, a role for which he won three Emmy Awards for Outstanding Supporting Actor in a Comedy Series from 2004 to 2011. On the other hand, Cruise made a brief but memorable appearance in 2008’sTropic Thunderas Les Grossman, the foul-mouthed, short-tempered, and balding studio executive behind the production of the eponymous Vietnam War film.

Now on X, formerly Twitter,Jeremy Pivenwelcomed the idea of a negotiation face-off between Ari Gold and Les Grossman. Check out the interaction below:

Tom Cruise as Les Grossman in Tropic Thunder

The idea was proposed on X by @PoorWorkHabits, who wrote, “How is it that we never got super agent Ari Gold negotiating mano-a-mano against mega producer Les Grossman in an @SNL or @CollegeHumor sketch? You game, @jeremypiven and #TomCruise? #MillennialDreams.” Piven responded, “Challenge accepted.”

Who Would Win A Negotiation Face-Off Between Ari Gold & Les Grossman?

A negotiation face-off between Ari Gold and Les Grossman, especially with Piven and Cruise reprising their roles, is certainly a great idea for aCollege HumororSaturday Night Liveskit. Speculating about who would win a negotiation face-off between the super agent and mega-producer is also an interesting hypothetical to indulge in. First off, it’s worth considering thatboth fictional characters were based on real-life figuresthat heavily influenced the creative choices made by their respective actors, and ultimately their portrayals on screen.

Yes! More Les Grossman Is Exactly What Tom Cruise Needs After M:I8

Tom Cruise is Hollywood’s biggest action star, but a return to his Tropic Thunder comedy character, Les Grossman, is perfect for his next movie.

The entire premise ofEntourageis loosely based on Mark Wahlbergand his interactions with his group of friends, and the character of Ari Gold is specifically based on the actor’s real-life agent, Ari Emanuel. On the other hand, some commentators and Hollywood insiders have speculated that Les Grossman is loosely inspired by film producers Scott Rudin and Harvey Weinstein, who are known for their explosive tempers and mistreatment of others. Weinstein would later, of course, be convicted of sexual harassment and rape.

Entourage TV Series 2004 poster

Though Ari Gold and Les Grossman are both larger-than-life Hollywood power players with aggressive approaches, their negotiation tactics are quite different.Entourage’s Ari Gold is a seasoned agent known for his quick wit, charisma, and deep industry connections, while Les Grossman is more of a one-dimensional comedic character, his negotiating style defined by dominance and fear. Overall,Ari Gold’s finesse and strategic thinking would simply give him the upper hand in a negotiation with Les Grossman. If the sketch idea ever happens, it would certainly be hilarious to see.

Entourage

Cast

Vincent Chase, a young and talented actor, embarks on his Hollywood journey surrounded by his loyal friends from Queens. His inner circle includes Eric, his dedicated manager; Johnny Drama, his supportive but fame-seeking half-brother; Turtle, his fun-loving and resourceful friend; and Ari Gold, his fiercely determined agent. Together, they navigate the complexities of the entertainment industry, balancing career aspirations with personal relationships, and facing the ups and downs of fame with camaraderie and resilience.

Tropic Thunder

Written and directed by Ben Stiller, Tropic Thunder follows a group of bumbling actors attempting to make a Vietnam War film, who find themselves dropped into a real-life warzone when they are abandoned in the middle of the jungle they are shooting the film in. Stiller also stars in the film, with an ensemble cast that includes Jack Black, Robert Downey Jr., and Jay Baruchel.

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