Ben Stiller in Zoolander. Photo: Paramount Pictures

Though it later became a comedy touchstone, the original Zoolander wasn’t a huge hit at the time of its release, earning only $45 million domestically. The reason? As you might recall, the movie was released only a few weeks after 9/11, a time when America wasn’t quite ready to laugh at the antics of an airheaded supermodel. Besides possibly being the reason Zoolander had to wait 15 years to get a sequel, this terrible timing also meant that, over the course of its life, this seemingly innocuous movie managed to get embroiled in three separate 9/11 controversies. What better time to revisit them than now, as the reportedly terrible sequel arrives in theaters?

1. The Skyline Edit

The first came from a controversial decision the film made regarding a shot of the New York City skyline, which had been shot while the World Trade Center was still standing. Like plenty of other filmmakers in the wake of the attacks, director Ben Stiller was faced with an impossible decision: Leave the shot as is, giving the audience a painful reminder of the recent tragedy in the middle of a dumb comedy, or edit the towers out and make it seem as if they never even existed? He went with the latter. For some audience members, it was the wrong choice. As critic Keith Phipps later recalled:

I couldn’t get my head around what I was looking at in one scene filmed against the backdrop of Lower Manhattan. Here was New York without the twin towers, by then a familiar sight from the news, but looking peaceful on a sunny day, as if the buildings had never been there. Anyone seeing the movie now, out of context from that moment, wouldn’t give it a second thought. At the time, it looked obscene.

2. The Foreign-Relations Accusation

As it happens, another critic at that same screening also thought Zoolander was morally abhorrent. In his infamous one-star review of the film, Roger Ebert did everything short of accusing the film of inspiring 9/11, thanks to what he saw as its insensitive treatment of the Malaysian prime minister and the country in general. “There have been articles lately asking why the United States is so hated in some parts of the world,” Ebert wrote. “As this week’s Exhibit A from Hollywood, I offer Zoolander, a comedy about a plot to assassinate the prime minister of Malaysia because of his opposition to child labor.”

As he concluded, the film seemed poised to inspire even more resentment toward America around the globe: “The more you put yourself into the shoes … of a Muslim 12-year-old in a sport-shirt factory, the more you might understand why he resents rich Americans, and might be offended by a movie about the assassination of his prime minister … Kids like that don’t grow up to think of America as fondly as the people who designed his flag.”

When it comes to inappropriate responses to 9/11, Roger Ebert’s Zoolander review was relatively harmless. Still, as Stiller remembered after Ebert’s death, the legendary film critic eventually apologized to him for pouring so much invective into the review. According to Stiller, “He said, ‘Hey, I just want to apologize to you. I wrote that about Zoolander, and I [now] think it’s really funny. Everything was a little crazy [back then]. It was Sept. 11 and I went overboard.’”

3. The Oliver Stone Billboard

Those were just the run-up to the third, weirdest Zoolander-9/11 controversy. Five years after the attacks, Hollywood was finally ready to address September 11 head-on, and Oliver Stone’s World Trade Center was one of the first movies out of the gate. The attacks are not shown explicitly on-screen. Instead, we simply see the shadow of an aircraft gliding along a New York City streetscape … which just so happens to include a Zoolander billboard. (You can see the moment at 29 seconds in the film’s preview.)

The sight is hardly anachronistic; New York City was plastered with Zoolander ads in the late summer of 2001. But as blog-era internet sleuths pointed out, photos from the time seem to indicate there was no Zoolander billboard at the intersection in question, and wasn’t it fishy that both films were Paramount releases? The implication was gross to the extreme: Was the studio tastelessly using a movie about an American tragedy to plug one of its other films?

Ten years on, that question hasn’t been fully answered. But in an appearance at Lincoln Center in 2005, Stone seemed to hint at another reason for the billboard’s inclusion. As the Columbia Spectator reported:

Last fall, the director told a Lincoln Center crowd that launching such a silly movie in the direct wake of an American tragedy was an affront to those who had their lives taken from them on that fateful morning. So fervent was Stone’s indignation, that, in his World Trade Center, the shadow of American Airlines Flight 11 passes across a Zoolander billboard as it plummets toward the North Tower.

In this telling, the fateful billboard was not a cross-promotional effort at all but rather a veiled slam on Stiller & Co. for releasing the movie at all. The Spectator report is the only source we could find that makes this connection, but it seems valid to us — almost poetic, even. As in any great tragedy, one fateful decision has had unexpected consequences: For erasing the World Trade Center, Zoolander will keep being haunted by its ghost.