Entourage‘s Ari actor Jeremy Piven welcomes a negotiation face-off with Tom Cruise’s Tropic Thunder character. 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’s Tropic Thunder as 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 Piven welcomed the idea of a negotiation face-off between Ari Gold and Les Grossman. Check out the interaction below:

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 a College Humor or Saturday Night Live skit. 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 that both fictional characters were based on real-life figures that heavily influenced the creative choices made by their respective actors, and ultimately their portrayals on screen.

The entire premise of Entourage is loosely based on Mark Wahlberg and 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.

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.