Haley Joel Osment Talks Hollywood, "Entourage," and Taking Risks

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From "The Sixth Sense" to "Entourage"—Haley Joel Osment invites us along for the ride.

Apr 28, 2014 | 11:11 AM

You would think Haley Joel Osment knew Hollywood inside and out. In fact, after getting an incredible start at a young age in iconic films like "Forrest Gump," "The Sixth Sense," and "Pay It Forward," the 26-year-old Academy Award nominee spent a good deal of time away from the land that launched his career. He graduated from NYU's Tisch School of the Arts, lent his voice to the popular "Kingdom Hearts" video game series, and made a 2008 Broadway run in David Mamet's "American Buffalo" alongside John Leguizamo and Cedric the Entertainer. Now, with recent roles in Will Ferrell and Adam McKay's hilarious tongue-in-cheek IFC miniseries "The Spoils of Babylon," and Kevin Smith's upcoming horror film, "Tusk," he is taking risks and stretching his legs in an industry that rewards the bold. 

And of course, risk-taking is the name of the game in his latest project, the feature film for "Entourage," based on the popular television series about a group of New Yorkers navigating La-La Land at its biggest and most bombastic. Dropping Haley in with fellow "Entourage" newcomer Billy Bob Thornton and longtime series stars Adrian Grenier and Jeremy Piven, it promises to be a wild ride of its own.

We caught up with Haley, who answered a few of our questions about his return to Hollywood and gave us a little insight into life on the set of "Entourage." Read on for his Q&A and photo diary.

Jeremy's, Billy’s, and my chair waiting (and staying mostly empty) on Day One of the production. The three of us got to kick off the "Entourage" shoot with some relatively contained scenes. On a show where scenes can balloon up and include hundreds of extras and lots of action, I think we all enjoyed getting to work with each other and Doug in close quarters.

WhoSay: Much of this cast has been working together for years—what is it like jumping into that group dynamic? 

Haley Joel Osment: You could tell that everyone was really happy to be back together again. They developed those characters and their relationships over a decade, and it was like watching childhood friends reunite when everyone jumped back into their roles.  

Mark Wahlberg drawing the winner of “Five Dollar Friday” (a ubiquitous on-set tradition) on my last day of shooting as Adrian Grenier looks on. 

WhoSay: Having been immersed in movies at a young age, would you say the Hollywood reflected in "Entourage" reflects your own experience in any way? 

Haley: I was not even a teenager when I did most of my studio films and I’ve been living in New York City since I was 18 years old, so the world of "Entourage" (and Hollywood itself) seems very new to me! It was fun to be inaugurating a period of working more in L.A. post-college by diving in with these guys. "Entourage" showcases the fun the industry has off-set, but it also portrays people obsessed with making big movies, and that’s an exciting environment to work in.

Emmanuelle Chriqui and I, giving my sister a hard time (the two of them worked together on "Cleaners" in Puerto Rico last month). Emily kept being too busy to visit us on set and had to leave town suddenly the last time we were available. Next time!

WhoSay: You've made some very eclectic choices over the course of your career—even just lately, you've acted in the IFC comedy "The Spoils of Babylon" and Kevin Smith's upcoming horror film, "Tusk." What governs the decision on whether to take a role? Has this evolved over time? What drew you to this role in "Entourage?"  

Haley: Going to college was a certainty since I was a kid (my parents insisted, thankfully) so going off to the other side of the country and focusing on that I think helped me get some perspective on why I do the work that I do and what I want to achieve. It also allowed me to do some theater and work extensively with a group of people my own age for the first time. After being mostly absent from the industry in that way, you do have to re-establish yourself, but it gives me the opportunity to stretch myself and do a variety of projects like the ones you mentioned. I feel very fortunate to have done larger studio films and smaller, more exotic ones! My primary reason for taking any role will always be the quality of the material. As for "Entourage," I just went in and auditioned and Doug and I hit it off. Lucky to be a part of this one.

It felt like half the NFL came to set during the week we shot one of "Entourage’s" signature party scenes at a beautiful house overlooking the ocean in Palos Verdes. Rob Gronkowski and Doug Ellin faced off in ping-pong while the cameras and lights were being moved around.

Watch for "Entourage" in theaters in 2015. 

Follow Haley Joel Osment on WhoSay for more insights into "Entourage" and amazing behind-the-scenes photos like this one: 

Cover image credit: Getty Images:

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