On an August morning Phillip Iscove is sitting across from me in the lobby lounge of the Beverly Hilton with a grin that says, “This is just great!”
It is. Minutes earlier, Kevin Reilly, boss of the Fox network, had told assembled critics that the new series Sleepy Hollow was “surefooted” and “in the sweet spot.” He also confirmed that the series would get a great time slot on Monday nights at 9 p.m. when it begins airing starting on Sept. 16. (In Canada on Global.)
Iscove, a boyish looking 33-year-old, Toronto-born, Northern Secondary and Ryerson graduate, is the co-creator of Sleepy Hollow. It’s his baby, his entry into big-time network TV.
This story you’re reading is a happy-ending tale. It says, “If your kids say they want to work in TV, create TV shows and get on a network, then don’t dismiss the dream. It can come true.”
Me, I’d never heard of Phillip Iscove until a few months ago. A man who works on Republic of Doyle told me to check out Sleepy Hollow, because the guy who created it worked at Bay St. Video in Toronto years ago and he knew him then. The nice young man at the video store, I was told, was certain he would end up in L.A. making movies or TV. And, by heavens, he’d done it.
Sleepy Hollow is a clever, twisted reboot of Washington Irving’s classic story The Legend of Sleepy Hollow. In this version, main character Ichabod Crane (Tom Mison), is one of George Washington’s leading soldiers in America’s Revolutionary War.
During a battle, Crane beheads a strangely clad, masked man. Crane too is injured and appears to die. Then he wakes up 250 years later, in the present, in the town of Sleepy Hollow. Mystified by the modern U.S., he soon finds that he’s being pursued by the headless figure he thought he had long ago killed. And, wouldn’t you know it, that guy’s actually the Headless Horseman, now one of the signs of the Apocalypse.
Turns out the Revolutionary War was a battle between good and evil. And evil is now running around Sleepy Hollow killing people. Crane teams up with a local cop to stop the mayhem and, he hopes, bring his wife into the future with him.
“I wanted to do a time travel show but leave aside all the things that make it geeky,” Iscove says. “I loved the Tim Burton movie Sleepy Hollow and started looking at the original material by Washington Irving. His story about Rip Van Winkle inspired my show, crossed with Twin Peaks, I guess, another show I loved. I wanted the show set in a spooky, dreamlike place. But it had to be modern, not a period drama. Modern is very important to the viewer and we’re giving them a new spin on something they thought they knew.”
I put it to Iscove that Sleepy Hollow is an “American Origins” drama. Although the pilot episode is vastly entertaining, it establishes the founding of the U.S. as a triumph against evil. It could be seen as politically loaded. Its themes fit neatly into contemporary U.S. politics, with the intentions of “the founding fathers” and the meaning of the U.S. Constitution debated endlessly by Democrats and Republicans, each trying to own the spirit of the American Revolution. It’s a bit odd for a Canadian to delve into this territory.
“Well, yes and no,” Iscove says, a little cautiously. “In Canadian high schools there is always this awful, painful question posed to students: ‘What does it mean to be Canadian?’ That always made me think, ‘What do American students say when asked, What does it mean to be an American?’ As a Canadian I can stand back a bit from the U.S. and wonder about the meaning of the founding of the country. I think the show approaches politics from a very neutral perspective. We’ve got Ichabod Crane thrown into the present and looking at the ideals he fought for, very puzzled by how it all worked out. He’s not condemning. Just curious. It’s not a heavily political show.”
Iscove, who describes himself on his Twitter account as “a neurotic Jewish writer living in L.A.”, looks a little neurotic now, but relieved he’s dodged saying anything inappropriate about a political message in Sleepy Hollow. He practically says, “Phew!”
He’s not used to interviews, the scrutiny. But he’s happy to talk about how he got from home, at Avenue Road and Lawrence Avenue in Toronto, to here, with a hot show on Fox. “I always, always wanted to make movies,” he says. “When I went into Ryerson I wanted to be a movie director. By the time I graduated, I knew I wanted to write, not direct. I wasn’t thinking about TV at all but I came around to the possibilities. ”
And the video store? “I worked at several video stores in Toronto when I was at Ryerson. I loved it. A job in a video store allows you to watch a lot of movies and TV shows. And then people ask your opinion about them and you have to express what you think. That’s useful.”
He ended up in L.A. through determination and good luck. His dad knew someone who knew someone who knew someone at United Talent Agency. He landed the archetypal job at the bottom – in the mailroom. “I never imagined myself working at a talent agency,” he says. “I wasn’t even sure what these agencies do. But I literally started pushing the mail cart around the office and gradually learning what the agency did. Eventually I was made an assistant in the TV literary department. I had to learn about how deals get made. It was like a post-graduate degree in film and TV.”
Along the way, he wrote pilots for TV shows. “I wrote five. I wrote them sitting at the desk of the guy who was my boss, when he wasn’t there. He gave me feedback, every time. You hear these stories about Hollywood being a very cruel place. I was lucky to meet people who wanted to help me. I used to work for the man who is now my agent.”
He remembers his breakthrough, exactly, and his eyes light up. “It was Feb. 27, 2012. I pitched Sleepy Hollow to Alex Kurtzman [producer of Alias, and Fringe]. That day, my life changed. It’s an amazing feeling when a producer smiles at you and says, ‘I love your idea.’ ”
Iscove says his pilot proposal was “general” and Kurtzman then developed it further. Both are officially “co-creators.” As he tells me his step-by-step account, his body language changes and his voice gets excited, reliving it. “In July of 2012 we went to Fox, the first network we decided to approach. We met Kevin Reilly in his office.”
At this point, I’m on tenterhooks too. And what happened? “He bought it. In the room.” Iscove says, “In. The. Room.” He also tells me Fox bought the pilot just weeks before his work visa in the U.S. expired. He practically says, “Phew!” again.
Later that day, at a lavish party thrown by Fox (Zooey Deschanel in the corner talking up New Girl, Gordon Ramsay trying to get to the food table), I ran into Iscove again. More relaxed now, he wanted to know when this article would appear, so he could alert family and friends in Canada. Then, I felt a tap on the shoulder and heard a voice say, “Hey, John Doyle.” It was Hart Hanson, the veteran Canadian writer/producer who started on The Beachcombers, went on to write for such U.S. shows as Judging Amy and is now the showrunner of Fox’s long-running hit Bones. I introduced him to Iscove, who looked a little awed. Hanson talked studio facilities, shooting schedules and timeslots with Iscove.
As I left them to it, I could see Iscove had that grin again. The one that says, “This is just great.”Report Typo/Error