Nicolas Cage was originally considered for the role of Brad Hamilton, but after his audition the studio thought his performance was too dark and the role went, instead, to Judge Reinhold. Additionally, Cage was 17 at the time and could not work as many hours as actors over 18.
Cameron Crowe wrote the screenplay based on his book. Cameron Crowe attended University of San Diego High School, he posed as a student at Clairemont High School. The principal then was not thrilled with the idea, but when he asked Crowe about musicians that he had met, he mentioned Kris Kristofferson. The principal was a big fan of Kristofferson and agreed to let Crowe on campus.
The mall scenes were filmed at the Sherman Oaks Galleria. It was damaged by earthquake in 1994, but still stood until 1998, when it was renovated and extensively re-designed by the architectural firm of Gensler for developer Douglas Emmett. Other than the parking structure, nothing recognizable from the 1980s era mall remains, the building having been converted from an enclosed, multi-story space to an open, mostly single-story mall.
Sean Penn improvised during his takes and tried to find ways to aggravate actor Ray Walston, who played Mr. Hand, even off camera. He also did things to get genuinely startled reactions from the extras who played his classmates through unexpected improvisations.
The scenes in the mall were shot during the night from when the mall closed at 9:30 to when it opened at 9. The two kids who Damone scalps the tickets to, were under 18 and due to labor laws couldn't film past certain hours, so they only had a 10-minute window to shoot their scenes
Near the beginning of the movie, right after Mr. Hand sends Spicoli to the front office for being late to class, Mr. Hand passes out the class schedule of quizzes. After the paper is passed out, the students put the page up to their noses and deeply inhale. This was a popular school ritual of the '60s, '70s and early '80s as photocopying machines were very expensive, so spirit duplicators were used. The spirit duplicators used a colored wax as the "ink" and a noxious solvent as a transfer agent to impress the ink on the paper. These solvents sometimes took a long time to dry, hence the students' use of these solvents as a short-term "high".
In the tradition of E.T. the Extra-Terrestrial and Reese's Pieces, this movie product-placed an obscure brand and it became famous: The checkerboard canvas decks Spicoli hammered himself with, Vans, became a national brand soon after.
Brad's job, requiring him to wear a pirate costume (which he hates), may have inspired a series of commercials for a credit report service where the spokesman is identically dressed, running as of 2008.
During a July 2008 interview with the Orange County Register about Pineapple Express, the interviewer told Seth Rogen and 'James Franco' that he prepared for the interview by watching the classic stoner comedy Fast Times at Ridgemont High the night before. When he asked Rogen and Franco if they prepared likewise before making Pineapple Express, Franco said he prepared by making out with Spicoli (a reference to his having shot Milk, in which he and Sean Penn play lovers).
In the dugout scene, the words 'Disco Sucks' are seen in the background. This is a reference to Disco Demolition Night where Chicago Radio Legend Steve Dahl, a favorite of a few members of the cast, blew up disco records at Comiskey Park while leading a cheer of "Disco Sucks"
First-time director Amy Heckerling said she was seeking to make a comedy that was less structured than conventional ones, and more like American Graffiti so that "if you woke up and found yourself living in the movie, you'd be happy. I wanted that kind of feel."
There are numerous references to rock bands throughout the film (shirts worn by characters, posters on walls, Damone is a ticket scalper, etc.) This is because Cameron Crowe was a writer for Rolling Stone magazine, and that job is how he first came to fame.
Vincent Schiavelli's character, biology teacher Mr. Vargas was based on Clairemont High School biology teacher George L. Jones. Jones kept many animals in class (rattlesnakes, entire beehives, bats) and would regularly take students on strange field trips such as visiting the San Diego sewage treatment plant or to watch surgery on pigs at the University of Calif. San Diego. Jones taught at Clairemont from 1962 to the 1982.
A scene where Mike Damone (Robert Romanus) was full frontal nude was originally in the movie, but had to be cut due to getting an X rating. It was either that or the 'carrot scene' had to go, and Romanus was happy for that.
Mike Damone's (Robert Romanus') nude scene with Stacy that was filmed and never used was stated by director Amy Heckerling to show the natural vulnerability between two young teenagers. The intent was to show each of them undressing, and then show them standing before each other fully naked, full frontal, vulnerable, and nervous. The scene was pulled due to an impending X-rating and has never been released.