Matt Dames/Sony/Getty Images; Warner Bros
May 22, 2015 08:50 AM

Living the Yacht Life

Leonardo DiCaprio and Adrian Grenier
KVS/Gaz Shirley/Pacific Coast News; Warner Bros

Leo: A regular at the star-studded Cannes Film Festival every year, Leo always comes to party–and relax. Most recently he was spotted sunbathing on the luxurious 16-person yacht Rising Sun with fellow 1993 What’s Eating Gilbert Grape costar Juliette Lewis. All that bidding can be exhausting.

Vince: One thing we know about Vince – he goes big. Real big. In the opening scenes of the much anticipated Entourage film, out June 3, Vince and crew are seen partying it up on a yacht filled with many, many topless models, off the coast of Ibiza (actually filmed in Miami).

The Winner: Vince may take this one from Leo for the sheer number of boobs, beers and bros.

Their Entourages

Vivien Killilea/Getty; Warner Bros

Leo: Before there were Vince, E, Drama and Turtle, there was Leo and his posse. Catapulted to stardom for his turn in 1997’s Titanic Leo owned the party scene in the late ’90s along with his tight-knit crew of Spider-Man‘s Tobey Maguire, Lukas Haas, and – surprise! – Kevin Connolly of Entourage. Recently Leo has been engaging in a bromance with fellow A-lister Bradley Cooper.

Vince: What would Vincent Chase be without his band of Queens-born brothers? There’s E (Kevin Connolly), best friend, manager, and voice of reason. Then there’s Turtle (Jerry Ferrara) who in the early Entourage days just smoked, drank and traded on Vince’s name to get girls, but later became self-made millionaire. And then there’s Drama (Kevin Dillon), who as Vince’s much older half-brother can always be counted on for unrelenting support of “baby bro” and his ludicrous yet entertaining one-liners.

The Winner: Leo was the first to perfect the art of the Hollywood party posse.

Girls, Girls, Girls

Leonardo DiCaprio (left), Toni Garrn, Emily Ratajkowski, Adrian Grenier
RGK/Pacific Coast News; Warner Bros

Leo: Perhaps the only thing longer than his list of films is his list of gorgeous girlfriends. The Victoria’s Secret catalogue could second as Leo’s little black book. He’s dated Gisele Bündchen, Bar Refaeli, Erin Heatherton and last year’s Toni Garrn. Lately, he may have switched from shopping VS to SI: He’s been spotted out with Sports Illustrated‘s 2015 Rookie of the Year, Kelly Rohrbach.

Vince: Like Leo, Vince is a ladies’ man; unlike Leo, he does not seem to have a type. Vince has been linked with costar Mandy Moore (playing herself), powerful Hollywood agent Amanda Daniels (San Andreas‘s Carla Gugino), porn star Sasha Grey (playing herself) and he ended the TV series by whisking away Vanity Fair writer Sophia (Alice Eve) to Paris to get married. And in the Entourage movie, he gets flirty with Emily Ratajkowski.

The Winner: Though Vince gets points for originality, Leo takes this category for the numbers and consistency.

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Their Power Agents

Rick Yorn and Christina Yorn (left) Jeremy Piven
J. Vespa/Wireimage; Warner Bros

Leo: Manager Rick Yorn is the Hollywood heavy hitter who has long represented Leo. With an elite list of clients who include Martin Scorsese, Reese Witherspoon and Jude Law, Yorn is a powerful name in the entertainment industry that makes the deal happen. And like Entourage‘s Ari Gold, Yorn famously left a big agency to start his own company, LBI Entertainment.

Vince: One of the most loved and hated characters on Entourage is superagent Ari Gold, who became a sensation in the hands of actor Jeremy Piven. Gold is known for his unrivaled temper, salacious insults but most of all his power. Said to be based on real-life agent Ari Emanuel, Ari Gold’s bravado is what turned young Mentos ad actor Vinny Chase into a Hollywood superstar.

The Winner: Tie. We’re unwilling to insult either of these very powerful men.

Their Next Moves

Leonardo DiCaprio in The Revenant and Adrian Grenier in Entourage
New Regency; Warner Bros

Leo: Already generating early Oscar buzz is Alejandro Gonzélez Iñérritu’s The Revenant, in which Leo stars as Hugh Glass, an 1820s frontiersman who in a raw man vs. wild scenario braves 200 miles of desolate wilderness to seek revenge on those who left him for dead. Leo could pick up a fifth Oscar nomination and maybe his first win.

Vince: In the new Entourage film Vince is the lead and first-time director of the film Hyde, a dramatic thriller for which the Hollywood star has high hopes. Hyde is a risk for Vince, especially after his last gamble with Medellin was a colossal fail in Season 4.

The Winner: Leo. Vince may have a blockbuster franchise in his repertoire with Aquaman, but Leo has the accolades.

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