Pineapple Express Funniest Moments Ranked

Too often, stoner comedies are made about stoners rather than by them, but "Pineapple Express" has an authenticity which lends a real-world feel to the film's revelations regarding stoner culture. From poking fun at the politics surrounding America's most controversial plant, to the awkward relationship one has with their dealer, the humor is relatable, candid, and side-splitting. The funny factor is elevated by a cast loaded with stellar veterans of comedy: Seth Rogen plays Dale Denton, a costume-donning subpoena process server and full-time stoner; James Franco is Saul Silver, Dale's surprisingly gullible pot dealer; Silver's dealer, the ruthless Ted Jones, is played by Gary Cole; and Rosie Perez plays Carol, a crooked cop who is Jones's main partner-in-crime. 

The plot thickens when Denton arrives on Jones's doorstep to serve a subpoena, but inadvertently witnesses Jones commit murder with Carol at his side. Denton drives off before Ted or Carol make an ID, but drops his joint in his panic. Ted is able to identify it as his uber rare strain, Pineapple Express, and trace it back to the only two people he's sold it to — one of which is Saul Silver. Hilarity ensues as Silver and Denton do their best to evade Ted and his cronies, and it's so funny it's hard not to put the entire script on this list. It's a tough job, but after revisiting the film again more than a decade later, we've broken down the moments that make us laugh hardest in "Pineapple Express."

Usually, plots are tied up with a nice big bow of character growth, resulting in positive changes in the way the heroes approach their lives. "Pineapple Express" pokes fun at this trope in the final scene, by giving the appearance that Dale goes on to pursue his passion and become a talk radio host. When the scene cuts to Dale, however, he is still freshly wounded from their escapades, and sitting in a diner with Saul and their newfound enemy-turned-friend, Red, played by the hilarious Danny McBride. 

As it turns out, Denton was only pretending to be a radio host, and the fact this trope gets flipped on its head somehow makes this reveal refreshing, as well as funny. The besties rehash all the highlights from the movie, and share some serious bromance moments. Saul even spoon feeds Red, and the trio share a hand-touching moment after Dale says, "We became friends along the way, and we learned some stuff about life too." 

After releasing each other's hands, Red slumps over with his eyes closed, and it appears as though he's succumbed to the many wounds he incurred during the course of the film. This movie doesn't allow itself to get that serious, however, and he re-awakens after gentle prodding from Dale and Saul. Then, Saul's beloved bubbie arrives to pick them up, played by firecracker Connie Sawyer, who tells them they smell like poop — only using a much more colorful word. What a sweet lady!

After Ted Jones is blown-up by a bomb thrown by a rival gangster, Dale delivers the subpoena that started this whole debacle to his dead body with the memorable line, "You've been served." However, Dale doesn't have time to gloat over surviving and being witty, because time is ticking, literally, and he must carry out an incapacitated Saul before Ted's hideout explodes. 

What makes this one of the funnier moments in the movie, however, is that he does it without any pants. After snubbing the now dead Ted, Dale realizes the bottoms of his pants are on fire, so he pulls them off rather than stop, drop, and roll — because, although that would be safer, it wouldn't set up the plot for a pantsless Seth Rogen. 

There's something particularly cheeky about the main protagonist running in slow-motion in tighty whities and blue and red striped socks. It would sure make for creative cosplay, if anyone had the courage to walk around in their underwear.

The final showdown tying up our heroes' struggle is chock full of hilarious moments. When facing off against the corrupt "lady cop," Carol, Saul yells the name of a controversial NWA song (only he wasn't singing) at her while firing off a high caliber rifle. Having no prior experience with firearms, however, he underestimates his own ability to aim, along with the massive gun's recoil. 

As a result, he completely misses Carol, even though she is feet away from him in the same room. What seemed like Saul's shining moment turns out to be an epically hilarious failure. When Dale finds himself duking it out with Ted, he finds unexpected and creative ways to defend himself. In one of the funniest moments in the film, Dale aggressively pinches Ted's nipples, which works quite well in disabling his foe. 

In the end, Dale and Saul wind up the surviving parties, thanks to a combination of luck and their unconventional fighting styles. Also, Red pulling up unexpectedly and running over Ted's last surviving goon with his Daewoo sure helps — and is as awesome as it is funny.

After Saul is kidnapped by Ted and crew, Dale feels compelled to go rescue his friend, but realizes he's going to need help infiltrating Ted's complex. So, he returns to Red's home, who was a fellow pot dealer under Ted Jones, and the only other person to hold Pineapple Express besides Saul. Red betrayed Dale and Saul by revealing their whereabouts to Ted, but Dale figured the enemy of his enemy made them potential allies. 

However, he finds Red bleeding out from gunshots dealt to him earlier by a few of Ted's goons. This is when "Pineapple Express" takes the opportunity to play on an action film trope, the "heroic second wind," which is mentioned by Saul verbatim for those who don't catch the joke right away. Despite his wounds, Red does indeed manage to conjure enough energy to get up and help Saul with his plan. 

Turns out, Red's more than prepared for such an occasion, because he has guns hidden in his wall behind a painting of a teddy bear with a cake — the origins of which are questionable, but never clearly explained. During their locking and loading montage, Red says hilarious quips like "Thug Life," and, "I used to use this gun when I was a prostitute." Red loses his second wind, however, upon seeing Ted's hideout, and suddenly recalling he "has a wife in jail" he "wants to have sex with" and he doesn't want to "wake up murdered tomorrow."

After having what he describes as a "near death experience," Dale calls his girlfriend, Angie Anderson (Amber Heard) and begs her to take him back after a recent break-up they had over the phone. He tells her he loves her, that he'll do anything to make it work, and breaks down crying hysterically. Angie starts sobbing too, telling Dale she still loves him, and hasn't been able to stop thinking about him. 

Seth Rogen's over-the-top crying is silly enough, but the scene takes an even more hilarious turn when Angie tells Dale she wants to marry him. This rom-com moment is shattered when Dale immediately stops sobbing, and questions her response rather than reciprocate her feelings. Then he awkwardly says, "Uh, I've made a mistake." Understandably, Angie is incredulous, and the two go on to bicker and argue over who is more immature. 

They also try to one-up each other by discussing their sexual experience and comparing partner numbers. When Dale mentions he's been with "two and a half" women, Angie asks what that even means, and tells him his hand "doesn't count." Good one, girl! Dale's reply is too explicit to repeat here, but his bizarre, albeit brief explanation is equally as funny.

Throughout "Pineapple Express," audiences catch glimpses of the quirky working relationship between Ted's main goons, Matheson and Budlofsky. The dynamic between these two characters is very silly, and made even more so because they're played by the hilarious Craig Robinson and Kevin Corrigan, respectively. Perhaps the funniest moment shared by these two takes place later in the film, when they're holding Saul hostage at Ted's "super cool" hideout. 

This is after Matheson got hit in the face with a coffee-pot by Saul, and the horrible disfigurement from boiling hot liquid and broken glass is as pretty to look at as Deadpool's unmasked face. Or, as Matheson puts it, "I look like Hamburglar and the Elephant Man." Then, he blames the accident on Budlofsky, because he ducked to avoid being hit, so the flying coffee-pot struck Matheson instead. Matheson then says one of his funniest lines in the movie: "I might act tough, but I got a lot of feelings, and you hurt damn near every one of them." Then he forces Saul downstairs, into a hidden underground passageway while threatening his life in one breath and telling him to watch his head on the way down the next.

It was just another workday filled with delivering subpoenas in various disguises while staying high as a kite, when Dale Denton delivered one last subpoena that would change his life forever. While casually blowing smoke rings and talking on his old school flip-phone before serving a man named Ted Jones, Carol the police officer pulls up directly behind Dale's car. Naturally, he freaks out, immediately ends the call, and ducks down in his seat. 

Luckily for him, she walks past the car without looking twice, and continues on straight into Ted's house, which Dale reacts to with a sigh of relief and renewed puffs from his joint. Not so luckily, a few moments later, Dale sees Ted shoot a man in plain view of his second-story window — along with Carol, who has joined him on the second floor. Rather than keeping quiet and lying low until he can make a quick getaway unnoticed, Dale panics as only a paranoid stoner can. 

Choking on smoke, he attempts to maneuver his boat-of-a-car out of its parallel parking spot, and in the process, repeatedly smashes into the cars he's parked between — including the corrupt "lady cop's" vehicle. So much for keeping a low profile! It's a side-splittingly hilarious moment, but unfortunately in his rush to drive off, Dale throws his roach of uber-rare Pineapple Express out the window. This ultimately leads the murderous drug lord, Ted, straight to he and Saul like a weed-smoking bloodhound.

In their pursuit to find Saul, Matheson and Budlofsky locate his grandmother, Faye Belogus, who he affectionately calls "Bubbie." The actress Connie Sawyer portrays Bubbie, who has been making people laugh for more than 50 years, and lends her comedic expertise to this role. She's staying in a retirement home, which is cheekily called "Pointe Break," and Matheson and Budlofsky are playing checkers with her in a common area while trying to learn Saul's whereabouts. 

In the midst of poorly staged small talk, and after exchanging awkward stares, a fight breaks out between the three men. In a quick-thinking moment of self-defense, Saul grabs a coffee pot off a hot-plate and throws it in the direction of Ted's two goons. Budlofsky ducks, and Matheson gets hit in the side of his face with the burning hot carafe. 

He goes down holding his face and whimpering, blood seeping through his hands — and although it's hard not to feel some semblance of pity for him, Saul is at least able to get away. The following scene depicts officers interviewing Faye and the other witnesses, who are witty and uproarious with their remarks. The scene closes with Faye trying to wipe what she thinks is dirt off the young officer's face in front of her, only to find it's a mole. Whoopsie!

Saul and Dale encounter many colorful characters during the course of their misadventures, and one of the more memorable of these is Danny McBride's hilarious portrayal of the very quirky Red. He rocks a shark-tooth necklace and Uggs, which are enough to make him stand out in a crowd, but he also has some bizarre notions, like claiming removing armpit hair makes him "more aerodynamic in a fight." These unique traits inherently make Red a very funny character, especially when he's first introduced, and he's become a fan favorite as a result. 

Interestingly, Seth Rogen revealed via Twitter that Red was supposed to be killed off the first time he was shot by Matheson and Budlofsky while tied up in his own apartment. However, the crew found actor Danny McBride so hilarious they decided to keep resurrecting him throughout the rest of the film. We're so glad Rogen and friends chose to keep McBride on for the entirety of the film, rather than kill him off early as originally planned. His near-death experiences make for some of the funniest moments in the film.

Dale's luck looks like it might be turning when he crosses paths with a Police Liaison Officer, played by Cleo King, who breathes comedy into her character's quirky mannerisms and saucy attitude. It doesn't seem like a fortuitous meeting at first — she'd just arrested Dale for selling pot to underage students at her school, and was taking him away in the back of her car after his ID returned a hit-and-run reported by the corrupt "lady cop," Carol. 

Saul escaped unscathed because he was away at the time buying snacks and frozen slushies, and hid when he came back and saw Dale getting arrested. As the officer drives off, Dale explains what happened with Carol and Ted, along with the murder he witnessed them commit. To his astonishment, she actually believes him, and says she even has a strong suspicion of which officer it might be. 

Dale's hopes are snuffed out, however, when Saul steals the car and leaves the officer behind — he thought he was helping Dale escape, and the officer was willing to help Dale until it was too late. The silly responses performed by Rogen and Franco are hilarious, and the scene gets even funnier when Saul tries to kick the front windshield out — only for his ankle to get stuck in a hyperrealistic display of what happens when not dealing with movie glass. When he finally pulls his ankle out, he excitedly declares, "Hey, I can see through my leg hole!"

Making first impressions can be intimidating, especially when first meeting the parents of a significant other. In "Pineapple Express," Dale botches his first dinner with Angie Anderson and her parents (played by Ed Begley Jr. and Nora Dunn) in about the worst ways possible. Not only is he very late, he's on the run from a trigger-happy drug lord, high, dirty, and covered in bruises and blood. 

When Dale is honest with them about witnessing a murder, and explains they need to leave for their own safety, the Andersons incredulous replies are understandable — but also funny, especially because they're peppered with F-bombs. The hilarity gets kicked up to the next level when Saul runs in, who unbeknownst to the Andersons was "keeping watch" outside, and came to warn them about the arrival of Matheson and Budlofsky. Angie screams and stabs Saul with a fork, Mr. Anderson runs out to get his gun, and Saul yells, "I'm a good drug dealer!" 

When Mr. Anderson returns, he is armed and points his gun at the boys while threatening to perform an intimate act on them in the street (only in much more adult terms) — to which Dale requests he not do that to them anywhere. The scene closes with the Andersons driving away, with Mr. Anderson saying to his daughter, "Angie, you're a bleeping idiot, and I say that with love." When Matheson and Budlofsky come in shortly afterwards, Matheson seductively touches the food while creepily saying, "It's still warm."

Out of all the side-splitting scenes in this comedic masterpiece, this is the one that has us rolling on the floor with laughter the hardest. After Dale attempts to rescue Saul from Ted and his goons, only to be captured too, the two of them have a moving "bromantic" moment and declare they are "BFFF's," which Dale declares stands for "best freaking friends forever" (only, he didn't say "freaking"). Then, Dale hatches a plan to free them from their bonds, by using the sharp edge of his belt buckle to cut through the ropes binding Saul. 

This leads into some of the funniest moments of physical comedy ever filmed, as Saul stands in front of Dale while vigorously rubbing his wrists against his crotch area while Dale thrusts back and forth to try and "cut" the ropes. It looks like they are doing something far more intimate, and Dale's commentary to Saul makes the innuendo even sillier and more apparent. "Rub your wrists on my belt buckle, man. I'm gonna save you man. I'll use my mouth, finish you off with my mouth..." 

Even funnier, Matheson keeps popping in every few minutes to tell them he can hear them through the walls. It's so hilarious, it makes one wonder how many retakes the scene required due to someone on-set laughing. Thanks for all the laughs, "Pineapple Express!" Too bad we will probably never get a sequel.