Judd Apatow's Love Of True Romance Helped Inspire Pineapple Express

Judd Apatow has had quite a run in Hollywood. A triple threat as a writer, producer, and director, he's responsible for dozens of TV shows and movies dating back to the early 1990s. But even in the early 2000s, Apatow didn't have the clout he has today.

On the heels of writing and directing "The 40-Year-Old Virgin" and "Knocked Up," Apatow was struggling to get his next project going — the coming-of-age teen comedy "Superbad," written by childhood friends Seth Rogen and Evan Goldberg. While waiting to get "Superbad" off the ground, Apatow asked the pair to continue working on another script. And the only inspiration they had to go on was a short scene from one of Apatow's favorite movies.

What Rogen and Goldberg came up with was the stoner action movie, "Pineapple Express." The film is a creative mashup that also confirms Hollywood doesn't always know what it's doing when the source material for a film is based on a stoned Brad Pitt.

"Pineapple Express" needed a raunchy teen comedy to both fail and succeed for it to ever exist. In a 2020 interview with Vanity Fair, Judd Apatow explained how the stoner movie came to be and the role that two other films played in making it happen.

"For years, Seth [Rogan] and Evan [Goldberg] and I were trying to get 'Superbad' made and nobody would pay for it," Apatow said. "And I was trying to think of something else that they could do that might be more commercial." The answer, Apatow went on to explain, was embedded within a 1993 Tony Scott film:

"I always had this idea about a pothead action movie because I love 'True Romance,' and there was that scene with Brad Pitt where all the assassins come in and he's really high and it was one of my favorite scenes. I thought, 'I wish that was the whole movie. I wish that you followed Brad Pitt out and he was on the run from the assassins.'"

And that's exactly what Rogen and Goldberg did. In "Pineapple Express," a weed dealer and his friend are on the run after witnessing a murder. Hilarity, hijinks, and plenty of pot smoking ensue in a unique blend of the stoner subgenre and a traditional action movie. But even after the duo wrote what Apatow called "an amazing script," they ran into another problem. They now had two scripts they couldn't sell.

All Seth Rogen and Evan Goldberg had to go on for inspiration for "Pineapple Express" was Floyd's minute-long interaction with the mob in "True Romance." It was enough — the duo hammered out "Pineapple Express" and Apatow shopped it around Hollywood. The project that was meant to hold them over until "Superbad" got produced, however, was even less appealing to studios. Apatow explained:

"And then we found out that ['Pineapple Express'] was way less commercial [than] 'Superbad' and everyone said no to that also. And only after 'Superbad' did well did somebody say, 'You guys have anything else?' And we were like, 'Oh yeah, this other thing that everyone rejects all the time.' And that was 'Pineapple Express.'"

When "Superbad" was released in 2007, it was an instant hit. At the time, /Film called the movie the best teen comedy since "American Pie," and it still holds up today. The film made stars of Jonah Hill, Michael Cera, and Emma Stone. And it also opened the door for "Pineapple Express."

So (and I wish we had a stoned Brad Pitt to explain this to us), a stalled "Superbad" project led to the creation of a "Pineapple Express" script, which couldn't get made until "Superbad" succeeded, which it eventually did, which led to the production of "Pineapple Express." And ... exhale.

"Pineapple Express" nearly recouped its budget on its opening weekend and ended up with a worldwide gross of more than $101 million, according to Box Office Mojo. That was just a year after "Superbad" grossed nearly $171 million worldwide. Three men, two scripts that nobody wanted, and $272 million. That's math that even Floyd could have handled.