As the creator of hits like The 40 Year Old Virgin, Knocked Up and Pineapple Express, Judd Apatow has taken on nearly every taboo. His latest project, however, will be his most controversial. “We’ve pushed the envelope with each release, but I think this time we’ve outdone them all,” proclaims Apatow, director and producer.

The film is called Pedovan, and it’s poised to be a yet another comedy classic, according to Shauna Robertson, Apatow’s production partner. “It’s pronounced ped-o-van, as in your feet,” she says. “Not pee-do-van. We’re hoping to have it out by Christmas 2009.”

The film centers around misguided hipster Glenn Davis (played by Jonah Hill), who makes several failed attempts to bring the children of his community joy. Hill’s character sports a bushy mustache, sideburns, dark glasses and thrift-store apparel. “He wears his clothes ironically,” explains Apatow. “People think he’s a pervert, but he’s a soft, lovable lug.”

After creating numerous doomed youth programs, Davis founds Ped-o-van (“Why walk when you can ped-o!”), a ZipCar-like community service where drivers pick children up from the park, their school or their extracurricular activities, and drive them home. All the vans are refurbished, soon-to-be junked conversion vans from the ’70s. “He loves these vans,” says writer Evan Goldberg. “And he loves these kids.” Davis equips the vans to run on biodiesel, so he must stop at fast-food restaurants to fuel up. The vendors start offering the kids free fries, inciting the wrath of high-strung parents concerned about children’s nutrition.

Shot primarily in Boston, local government officials have worked with producers to keep the shoot secretive, since Apatow feared any leak might spark protests and lawsuits that would slow down production, especially after the Tropic Thunder fiasco involving the film’s use of the word “retard.”

“Boston seemed the perfect place to make this film though. They’ve done everything in their power to get us here,” he says, referring to the way state and city government officials have been tripping over themselves to bring movie-making to the area, enticing the industry with everything from tax incentives to free police details.

Apatow and his crew were able to film throughout Boston without much notice, in part because the Department of Public Works agreed to claim streets were shut down for road repairs. However, Apatow added, “Bostonians are so accustomed to film crews now, they don’t even bat an eye. In addition, we don’t really have many celebrities in our movies–Martin Starr for instance. Nobody knows who the fuck this guy is!” Starr, known for his role in Apatow’s series Freaks and Geeks, plays Davis’ mentally challenged friend, Smitty Smitty, who still pines for his former special-ed teacher—now Davis’ girlfriend—Nancy Calliphogos (played by Leslie Mann—Apatow’s wife).

Tim Lochland, executive director of the Office of Film Industry Tax Relief (OFITR) couldn’t be happier that yet another film is being shot locally, and by Apatow.

“We’re overjoyed that Judd has finally come to Boston. His films are the talk of Hollywood right now!” Lochland adds that the Massachusetts’ tax credits now readily available to filmmakers will soon transform Boston into the new Vancouver of the film industry. Since the state removed the film industry’s tax credit-cap in July 2007, there have been 88 different productions filmed locally. Prior to the tax incentive, film production was rare in Massachusetts; in 2006, only four films were shot here.

“We’re becoming Hollywood East,” bellows Lochland.

So enamored with Apatow was Lochland, that he flew Apatow and five others nonstop from the Netherlands to close the deal. “We’ll no doubt get some criticism for this,” Lochland says, adjusting his monocle. “People will say, ‘Oh, there’s a budget deficit, and you’re spending money, blah blah blah.’ They don’t realize that when production companies come in, they stimulate the economy.” The OFITR then put Apatow and his entourage up in a penthouse, sparing no expense.

Stimulus aside, Apatow’s production company is eligible for tax credits covering up to 25 percent of their production costs and payroll (estimated around $28 million), and exempt from local sales tax. The tax incentives they’ll receive have undoubtedly gained popularity within the film industry. “It’s a great move for Massachusetts,” says Robertson. “We probably would have filmed here anyway, but with what the state brought to the table—the tax relief, the flight, the lobster dinner—it was a no-brainer.”

“Boston is so film-crazy right now,” says Apatow, “we even had a local investor buy all of the vans we used in the filming. He’s creating a chain of Pedovan tour buses, and using the actual vans … It’s kind of a genius idea. I wish I had thought of it.” These won’t be your ordinary tour buses either. Each van was outfitted specifically for its driver’s character in the film. Fitness guru Richard Simmons’ character (imaginatively named Dick Simmons) owns a van with a giant rainbow unicorn on it; the van is “pedo-powered” by its young passengers, a la the Flintstones. Harold Ramis’ “Jesus Van” has a window in the shape of a crucifix. Ramis plays Father George O’John, who was recently in prison for … tax evasion.

While successful in keeping the film secret despite such flamboyant props, the stealth shoot was almost blown. An Amber Alert during production drew suspicion to Rob Lowe, who plays the good-hearted but skeezy-looking John Smith (costumed in extra-dark glasses, a baseball cap and a trench coat due to a rare sun allergy). He was actually taken into custody.

“I guess he matched the description,” Robertson told us with a laugh. “Someone called to report him, and they took him in, and, well, let’s be honest, Rob actually has had trouble with this sort of thing before.”

To defuse any concerns, the production team agreed to allow Susan Philpot, the mayor’s “city censor,” on the set. She oversaw the handling of the child actors/extras and kept a close eye on other controversial cameos—such as R. Kelly’s. “R. Kelly plays a Chuck E. Cheese employee,” Robertson tells us. “His character won’t let Davis into the place without a kid.” Philpot’s presence was not without its own controversy. Rumor has it that she tried to dictate the content of the film once on set. She could not be reached for comment.

Cameos in Pedovan are about as frequent as The Muppet Movie. “When we heard someone was in town, we grabbed them,” says Robertson. “I can’t tell you who they are, we still need the releases, but one is the Celtics’ Glen Davis. We couldn’t help ourselves, I mean, his nickname is ‘Big Baby’ … our Glenn has two Ns.”

In keeping with Apatow’s other collaborations, the film is set in Clark County, with Bill Hader and Seth Rogen reprising their roles as local police officers—constantly busting Davis’ ill-conceived exploits.

The soundtrack is pure Apatow as well, considerably mining ’70s yacht rock, including “Ventura Highway” by America, “Couldn’t Get It Right” from the Climax Blues Band, “So Into You” by Atlanta Rhythm Section and, in the uplifting finale, England Dan & John Ford Coley’s “Love is the Answer.” Steely Dan was asked to contribute, but, as Apatow says, “They weren’t down with the subject matter.”

As in the case of Pineapple Express, Apatow has commissioned another famous rocker to write the theme song to Pedovan. “We’re really hoping Gerry Rafferty can write us a song about love for children,” he says. Rafferty was responsible for “Baker Street,” famously featured in the Boston/Cambridge-based Good Will Hunting and is perhaps most known for writing “Little Green Bag,” which appeared, so to speak, in Reservoir Dogs.

While the film wrapped up production last month, it’s not yet out of the woods. The release will undoubtedly spark outrage. But, given the fact that Hollywood seeks new ideas by merging disparate genres (as in Pineapple Express) and leaping over the lines of taste (Tropic Thunder), it seems Pedovan is just another film venturing into that frontier. As Robertson points out, the film lampoons our conceptions of pedophiles, not pedophilia itself. No doubt, watching it will both elicit laughs and make viewers uncomfortable, forcing them to question that discomfort.

When asked if this was his intent, Apatow said, “OK, yeah. Sure. Whatever.”