Columbia Pictures released the film on August 6, 2008, and it grossed $101.6 million worldwide. Franco was nominated for a Golden Globe Award for his performance in the film.
In 1937, a military facility is on watch behind a two-way mirror as a soldier, smoking marijuana, begins to reveal very graphically what he hates about the army, but still remains euphoric. A high-ranking officer immediately closes the project and deems marijuana illegal.
Seventy years later, Dale Denton, a 25-year-old process server and habitual marijuana smoker, makes a visit to the home of his drug dealer, Saul Silver, to buy marijuana. Saul tells him that he may already know the identity of Dale's next customer, Ted Jones. Dale drives to Ted's house and witnesses Ted and a police officer, Officer Carol Brazier, shoot a man to death. Dale panics and flees the area, but leaves his roach at the scene, which contains a rare strain of marijuana called Pineapple Express. Ted is able to identify the strain and sends his two henchmen, Budlofsky and Matheson to a dealer, Red, who tells them that he has only sold the pot to Saul.
Dale flees to Saul's apartment and learns that Ted is a dangerous drug lord and could trace the roach back to Saul. Dale and Saul flee into the nearby woods while Ted's henchmen persuade Red to arrange a meeting with Saul. They accidentally fall asleep in Dale's car and wake up to find that they missed their meeting with Red. They leave the woods and arrive at Red's house, hoping to determine whether Ted has linked them with the Pineapple Express. Red says Ted isn't after them but Dale realizes that he's lying, and starts a fight that results in Red getting knocked out. They wake Red and question him until he reveals that Ted has discovered who they are and is going to kill them. Dale and Saul decide that they must leave the city.
In order to leave town, Dale and Saul sell some Pineapple Express to raise bus fare. However, a police officer named Barber sees Dale and arrests him for selling marijuana. In the back of the cruiser, Dale tries to convince Barber that Brazier is corrupt and tells her that he witnessed her and Ted murder a man. Barber recognizes Brazier and promises him that she will investigate her soon since Barber had been long suspicious of Brazier's corruption. However, Saul leaps out in front of the police car and hijacks it thinking that Brazier is the one driving. Brazier hears a police radio call of Dale's arrest and pursues Dale and Saul in a high-speed chase but they manage to escape. After an argument with each other about the situation they are in, Dale and Saul go their separate ways. Saul visits his grandmother in an assisted living home, but is kidnapped and held hostage in Ted's lair beneath a barn. Dale enlists Red to help him rescue Saul but Red unexpectedly backs out at the last minute and Dale is captured. While Dale and Saul are held hostage, they reconcile with each other and make plans to escape.
Suddenly, Asian mobsters attack the barn to avenge a fellow gangster's death at the hands of Ted and Officer Brazier (the same murder that Dale witnessed). Dale and Saul finally free themselves but are caught by Matheson. Matheson grazes Dale's ear with a gunshot but is disarmed and shot by Saul. Dale and Saul join the fight and a brawl ensues between Dale and Ted. When Budlofsky refuses to kill Saul, Matheson emerges from the lair and shoots him in the chest, killing him. He turns around to kill Saul but Red drives through the barn and saves Saul by hitting Matheson with his car. Red is then seemingly shot to death by Brazier. One of the mobsters activates a bomb, resulting in Ted's death, and setting fire to the barn. When Red's car explodes, it flips over and lands on Brazier, killing her. The explosion incapacitates Saul but Dale finds him and carries him out of the burning barn. Red, wounded but still alive, also escapes and reconciles with them. Afterwards they eat breakfast at a diner and talk about their adventure before Saul's grandmother picks them up and takes them to the hospital.
The inspiration for making Pineapple Express, according to producer Judd Apatow, was Brad Pitt's character in True Romance, a stoner named Floyd. Apatow "thought it would be funny to make a movie in which you follow that character out of his apartment and watch him get chased by bad guys". According to Rogen, the ideal production budget was $40 million, but due to the subject matter—"because it's a weed movie", as he described it—Sony Pictures allotted $25 million. The movie is named after a real cannabis strain called Pineapple Express.
Rogen was originally going to play Saul, but Apatow suggested that Franco should play the role instead. After a table read, Rogen agreed, thus casting himself in the role of Dale Denton.
Seth Rogen spoke with musician Huey Lewis, of Huey Lewis and the News, about writing and performing the film's theme song in November 2007.
A "red-band" trailer for the film, featuring the song "Paper Planes" by M.I.A., leaked in February 2008. Sony Pictures had the video removed from YouTube within a few days of its posting. Patrick Goldstein's Summer Movie Posse of the Los Angeles Times described its incorporation as "the most impressive use of M.I.A.'s 'Paper Planes' ever". The film's makers had been keen on including the song in the film's main trailer and approached M.I.A.'s U.S. label Interscope Records for permission. She added "Interscope asked me and I was, like, well, since it’s just the trailer, that’s cool. I didn’t really think twice about it" stating she would have thought more carefully about permitting the song's use if it was in the main film, "scrutinizing what scene they were using it in and stuff like that". Pineapple Express had an advance screening at the Just for Laughs Film Festival on July 19, 2008. The film was released on August 6, 2008. Cable network FX pre-bought exclusive rights to air the film after its theatrical run. One particular aspect of the film that has been almost universally praised is the cinematography; Seth Rogen even joked on the commentary that "even people who hate the movie admit that it's shot well".
David Gordon Green met with Apatow, Rogen and Goldberg on the set of Knocked Up, and later on the set of Superbad to discuss the project. Green cited The Blues Brothers, Midnight Run, Running Scared, the Terrence Malick written The Gravy Train and Stir Crazy as sources of inspiration and influence on directing the film.
There was an exclusive sneak peek of the film attached to the Superbad DVD, which was released on December 4, 2007.
Sony released the film on Wednesday August 6, 2008 and it grossed $12.1 million on its first day. Over the weekend it opened at number two behind The Dark Knight with $23.2 million, a five-day total of $41.3 million. The film went on to gross $87.3 million in the US & Canada and $14.2 million in other territories, for a worldwide total of $101.5 million.
The film was released on DVD and Blu-ray on January 6, 2009. Both rated and unrated versions of the film are available. It was released on DVD and Blu-ray in Australia on December 31, 2008. Both the Blu-ray and 2-disc DVD versions of the film come with a digital copy of the unrated film. As of November 1, 2009 the DVD has sold 2,510,321 copies and generated $43,033,863 in sales revenue.
On Rotten Tomatoes, the film holds a rating of 68%, based on 193 reviews, with an average rating is 6.3/10. The site's consensus reads: "Both funny and scatter shot, this loose-knit action/buddy/stoner comedy bridges genres and keeps a steady tempo of low ball laughs." On Metacritic, the film has a score of 64 out of 100 based on 37 critics, indicating "generally favorable reviews".
Michael Phillips of the Chicago Tribune praised the film's script, noting that it "recalls what made Superbad worth seeing: the sidewinding conversational riffs, the why-am-I-laughing? wordplay." However, he was critical of the second half of the film, and felt that the violence in contrast to the comedy of the first half was jarring and gratuitous. Kelly Vance of East Bay Express enjoyed Franco's performance, stating that he "steals the movie easily", as well as the authenticity of the film's sets.
The original motion picture soundtrack to the film was released on August 5, 2008. Although featured in the trailer for the film, the song "Paper Planes" by M.I.A. is not used in the film or on its soundtrack. Following the trailer's release, "Paper Planes" gained massive airplay, entering the Top 5 on Billboard Hot 100. Also featured in the film but absent from the soundtrack album are Grace Jones' Sly and Robbie produced cover of Johnny Cash's "Ring of Fire", the former of which can be found on her 1998 compilation Private Life: The Compass Point Sessions.
- "Pineapple Express" by Huey Lewis and the News (4:27)
- "Electric Avenue" by Eddy Grant (3:48)
- "Dr. Greenthumb" by Cypress Hill (3:08)
- "Lost at Birth" by Public Enemy (3:33)
- "Poison" by Bell Biv DeVoe (4:20)
- "Wanted Dread and Alive" by Peter Tosh (4:22)
- "Don't Look Around" by Mountain (3:44)
- "Pineapple Chase (aka The Reprise of the Phoenix)" by Graeme Revell (3:03)
- "Bird's Lament" by Moondog & The London Saxophonic (2:02)
- "Coconut Girl" by Brother Noland (3:36)
- "Hi'ilawe" by Arthur Lyman (1:09)
- "Time Will Tell" by Bob Marley (3:31)
- "Tha Crossroads" by Bone Thugs-n-Harmony (3:45)
- "Pineapple Fight (aka The Nemesis Proclaimed)" by Graeme Revell (3:08)
- "I Didn't Mean to Hurt You" by Spiritualized (5:12)
- "Woke Up Laughing" by Robert Palmer (3:35)
Judd Apatow stated that there's a strong possibility for a sequel, but nothing is officially announced yet. A supposed trailer for the sequel was released on April 1, 2013 with Rogen, Franco, McBride, and Robinson reprising their roles, and Jonah Hill appearing as Woody Harrelson, but this was revealed later to be an April Fools prank, promoting their upcoming film This Is the End. According to Rogen and Goldberg, however, the homemade Pineapple Express 2 film in This Is the End depicts what they envision for the actual sequel. After the Sony hack in 2014, there was an email leaked saying that Sony does not plan to do a sequel to the film.