Hollywood Descends on Yorktown to Film The Pirate King

George Washington. General Rochambeau. Marquis de Lafayette. These are famous names you might associate with Yorktown, Virginia. But how about Jordana Brewster, Rob Riggle, and Josh Plasse? If you haven’t heard, our historic town is getting a taste of Hollywood!

The Pirate King stars Rob Riggle (The Daily Show, 21 Jump Street, The Hangover, Step Brothers) as a Marine veteran struggling with PTSD and addiction who finds redemption in a pirate reenactment group. Brewster (The Fast and the Furious franchise, The Texas Chainsaw Massacre: The Beginning) plays his love interest.  

Writer and actor Josh Plasse (iCarly, Grey’s Anatomy, The Baxters), a Virginia Beach native, wrote the screenplay based on a story by Brev Moss. It’s inspired by the adventures of real-life pirate reenactor, “Mister Willis” (Todd) of The Loose Cannon Company. You may remember this interview we recently shared with Willis, who has been partaking in pirate shenanigans in Yorktown for years at our many pirate and maritime festivals. Mister Willis is Plasse’s uncle. 

“Josh and I have been talking about this for about five years or so,” Willis said. “It started out as my life story, but he couldn’t sell that, so he changed it around a little bit. So, it’s a little bit about me, but it’s a lot about the guys he met while working with Mission 22, which raises awareness about the estimated 22 veterans who commit suicide every day.” Plasse's father was a Navy Seal, so the military has been a big part of his life.  

"Everything that’s in the movie about pirate reenactment really comes from me—the jokes and that sort of thing, some of the scenarios,” Willis told us. “But the basic meat and potatoes of the story is really about the veterans and the stuff that they go through.” 

After deciding on the concept, Plasse and Willis would chat once or twice a week to brainstorm different scenarios and how they would play out. Then, Plasse worked on financing and put together a package to pitch to producers. According to Willis, Plasse’s authenticity helped move the movie into production. “He’s a really good dude—when he tells you something, you can believe it because you can see through him, and his heart is good. And everybody else could see that too. That’s all I’d hear from his producers—about how much they loved the guy. And I told them, ‘Well, I love him too. He’s my damn nephew!’” Spoken like a true pirate. 

Around 150 people traveled to Yorktown for the week-long shoot, including the big-name actors in the film. “Rob Riggle plays a character named Todd Willis—crazy, huh?” Willis shared. “And Jordana Brewster plays his love interest, Laura. They’re all members of this company called The Loose Cannon Company, which is again, pretty crazy!”  

Willis told us the movie may get an R rating due to profanity, but it has a heartfelt family feel. “Rob really brings a lot to it,” Willis said. “He’s known for being a comedian—he's a very funny guy. But in this, he’s very serious too. He’s truly a gifted actor.” 

As for Willis, he’ll have a small speaking part in the movie. “I’m Civil War Jim," Willis told us. “That’s what Josh wanted me to do. I said whatever you want, I’ll do that. I’m supposed to be the most hated guy in the movie, so it’s kind of a natural thing for me.” (Again, spoken like a true pirate.) 

Willis isn’t the only local buccaneer you may recognize—three additional members of The Loose Cannon Company are in many scenes with the core group of actors. “I’ve been so jazzed to be part of this thing and able to share it with my company,” Willis said.  

Filming took place throughout the Hampton Roads area, including Virginia Beach and Norfolk. But for Willis, filming in Yorktown was extra special. 

"I’ve always loved Yorktown. Yorktown the city has been really good to us; the Watermen’s Museum has always been really good to us. It’s a close relationship, and we just love it here. It’s a beautiful place. There’s always something going on in Yorktown. During the summer there’s bands all the time—they have the markets on the weekends. It’s just a wonderful place to live. If I had to relocate, this is where I’d move.” 

The movie is expected to be released sometime next year. Count on us to keep you posted!