In an exclusive interview with E! News, the Sweetwater star said it "would be fun" to revisit the role, which he played for eight seasons, and see how the egocentric agent would maneuver around Hollywood these days.
"I think there's so many different ways we could go with Ari," he mused. "How would he navigate this climate?"
Of course, Piven noted that Ari's long-suffering right-hand man Lloyd (Rex Lee) would likely serve as his new "politically correct consultant."
"It would be fun to investigate where all these people would be today," he continued. "There's been so much that has happened since then that it'd be a very fertile ground to explore."
Looking back, Piven is "grateful" for fans' enduring love of the show. "I never would have guessed that we would have this type of reach," he admitted. "I'm out on the road doing stand-up comedy and you hear people screaming out lines and that they miss it. I never would have dreamt that we would have this kind of an impact."
In fact, Piven said he recently was able to reconnect with LeBron James, who appeared in a 2009 episode, when he took a trip to Salt Lake City to catch the 2023 NBA All-Star Game.
"It was incredible," Piven said. "I got to tell him [that] I haven't seen him since he did a cameo on Entourage 1,000 years ago. I'm just so proud of that guy, 20 years in the league and he's still absolutely crushing it."
And given how Piven plays famed basketball coach Joe Lapchick in Sweetwater, a biopic about NBA legend Nat Clifton, the full circle moment was not lost on him.
"Everything matched up," he said. "It's a miracle. This is a movie that will be very inspiring."
Sweetwater is out in theaters April 14.
—Reporting by Olivia Modarelli