- A process server and his marijuana dealer wind up on the run from hitmen and a corrupt police officer after he witnesses his dealer's boss murder a competitor while trying to serve papers on him.
- Lazy court-process clerk and stoner Dale Denton has only one reason to visit his equally lazy dealer Saul Silver: to purchase weed, specifically, a rare new strain called Pineapple Express. But when Dale becomes the only witness to a murder by a crooked cop and the city's most dangerous drug lord, he panics and dumps his roach of Pineapple Express at the scene. Dale now has another reason to visit Saul: to find out if the weed is so rare that it can be traced back to him--and it is. As Dale and Saul run for their lives, they quickly discover that they're not suffering from weed-fueled paranoia: incredibly, the bad guys really are hot on their trail and trying to figure out the fastest way to kill them both. All aboard the Pineapple Express.—Anonymous
- In 1937, a soldier (Bill Hader) in a military facility is being observed through a two-way mirror smoking marijuana and revealing in his euphoria what he hates about the army. A high-ranking officer closes the project and deems marijuana illegal.
Seventy years later in 2007, Dale Denton (Seth Rogen), a subpoena server visits his drug dealer, Saul Silver (James Franco), to buy marijuana (Saul sells dale a Pac of the Pineapple express blend, a rare kind of strain that recently hit the market). Saul says he may know Dale's next customer (to whom Dale is serving some court papers), Ted Jones (Gary Cole) (Saul buys his supply from Red, who buys it from Ted). At Ted's house (Dale is waiting outside to finish his joint when a police car pulls up) Dale witnesses Ted and a police officer, Carol Brazier (Rosie Perez), shoot a man dead. While fleeing, Dale leaves behind his roach (joint) containing Pineapple Express, a rare strain of marijuana. Ted identifies the strain and sends his henchmen Budlofsky (Kevin Corrigan) and Matheson (Craig Robinson) to Red (Danny McBride), a dealer who tells them about Saul.
Dale rushes back to Saul & at his apartment, Dale learns Ted is a drug lord and could trace the roach (as the Pineapple express is a rare breed of pot). Dale and Saul visit Red (who was already working with Budlofsky and had ratted Saul out), who reveals that Ted knows who they are and intends to kill them. Dale and Saul escape, as Budlofsky comes in and learns about Dale's involvement. Ted orders Budlovsky to kill Red. Meanwhile the Asian gang members are outside Ted's house and listening to all his conversations.
Dale shows up for dinner at his girlfriend's Angie (Amber Heard) parents' house and obviously it goes bad as Dale is bleeding and he stinks. Angie's dad pulls out his shotgun and starts shooting at Dale & Saul, but Dale manages to convince him to calm down. As Budlofsky reaches Angie's house (tracking Dale's car), Dale and Saul leave. Meanwhile Ted and Carol talk to the Asian mob boss Cheung (Dana Lee) and tell him that his assassin is dead. Ted promises retaliation if Cheung does not withdraw Dale. Ted thinks Dale is another assassin sent by Cheung. Cheng decides to attack Ted.
Dale and Saul decide they must leave the city. They sell Pineapple Express to raise bus fare, but Dale is arrested by Police Liaison Officer Bobbra (Cleo King). Dale tells Bobbra that he witnessed Brazier and Ted murder a man. Bobbra has long been suspicious of Brazier's corruption and says she will investigate; however, Saul, thinking that it is Brazier driving, hijacks the police car. Brazier hears on police radio of Dale's arrest and pursues Dale and Saul in a high-speed chase, but they escape.
After Dale and Saul argue (they call each other stupid and the main reason of why they both are in this mess) and split up, Saul is kidnapped (Budlofsky was waiting at Saul's grandmother's retirement home, when Saul visited her) and is held in Ted's lair beneath the same military facility from 1937.
Dale enlists Red's help to rescue Saul. Red had miraculously survived 2 gunshots to his body and arms himself and Dale, and drives Dale to the lair where Saul has been kept. Red backs out at the last minute and Dale is captured by Budlofsky. While Dale and Saul are waiting to be killed, they reconcile and plan an escape.
Asian mobsters attack the barn to avenge their fellow gangster's death, the murder that Dale witnessed. Dale and Saul free themselves but are caught by Matheson (Craig Robinson) (Matheson is Budlofsky's assistant and has been working with this entire time). A brawl ensues between the attacking Asians and Ted's forces who retaliate. There are heavy casualties on both sides. Saul takes on Brazier, while Dale combats Ted. Both manage to come out on top, but Matheson has the gun on Saul.
Red reappears and drives his car through the barn, killing Matheson and saving Saul, but is shot by Brazier. A mobster sets off a bomb killing Ted and setting fire to the barn. Red's car explodes and lands on Brazier, killing her. Dale carries Saul from the burning barn and Red, wounded but still alive, also escapes and reconciles with them. They talk about their adventure over breakfast at a diner before Saul's grandmother picks them up and takes them to the hospital.
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