Just because they're comedies doesn't mean they're all laughs. Some comedies hit hard in their portrayal of real-world events. Other comedies even revolve around a tragedy. Then there are comedies that manage to be funny and tragic.
In a horror film, the audience knows death is in store, and depending on the strength of the script they also often know exactly who it is who's going to be offed. Comedies have an advantage because outside comedy dramas like This Is Where I Leave You, comedies aren't typically marketed as being related to death. So, when a character (usually a very likable one) meets an untimely demise, it's a shock and oftentimes stands as one of the film's most memorable moments.
20 Bill Murray in Zombieland (2009)
Ruben Fleischer's Zombieland managed to be a box-office success in spite of leaking online while in theaters. Thankfully, for those who actually chose to see it in theaters, those who did not mostly avoided spoiling a certain elongated cameo.
Bill Murray starring as himself is perfect for a movie with a tone like Zombieland's, and it's blatantly the most fun he's had in years, both in terms of the movie and the real world. To him, the apocalypse ends up inspiring his prankster mind to dress up as a member of the undead. Unfortunately, this gets him accidentally killed by Jesse Eisenberg's Columbus.
19 Phil "Landfill" Krundle in Beerfest (2006)
As far as the Broken Lizard troupe's movies go, their fourth, Beerfest, ranks toward the top, arguably under only their second film: Super Troopers. But, it has a bigger surprise than any of their other movies.
Kevin Heffernan pulled off an impressive balancing act in that earlier film as Rod Farva, a character so unlikable it's amazing he doesn't tank the movie. And, not only does he help the movie instead of hurt it, he's arguably the most quotable character to come from a Broken Lizard project. So no one expected his character to die in Beerfest. In their previous film, the slasher-comedy Club Dread? Sure. But not his Landfill, who gets in a fight with Mo'Nique's character, Cherry, and is pushed into a vat of beer.
18 Marie Griffith in Planes, Trains and Automobiles (1987)
One of John Hughes' best in a line of great films, Planes, Trains and Automobiles is a great starter movie for parents looking to allow a first R-rated film. Heartfelt without ever being saccharine, it's also a movie with a sad but truly surprising twist.
The movie has the audience spend time exclusively with the odd couple pairing of Steve Martin's Neal Page and John Candy's traveling salesman Del Griffith, all under the pretense that the two men will be returning home to their significant others for the holidays. Unfortunately, it dawns on Page that some aspects of Griffith's story, specifically those regarding his wife Marie, don't add up. His suspicions are confirmed upon arriving at the train station, finding Griffith alone and sad. The once steely Page warms up one last bit, and Griffith is no longer alone for Thanksgiving.
17 Joe Mentalino in Dumb and Dumber (1994)
Save for perhaps There's Something About Mary, Dumb and Dumber is the Farrelly brothers' most hilarious movie. It's mostly Jim Carrey and Jeff Daniels' show as Lloyd Christmas and Harry Dunne, respectively, but the film is also populated with some very memorable supporting characters.
For instance, gangster Joe Mentalino, played by beloved character actor Mike Starr. Mentalino is targeting Harry and Lloyd, but Harry and Lloyd couldn't be more oblivious to this, even when he's sitting between them in their pup-mobile. When the trio stop at a diner, the idiotic titular pair attempt to pull a prank on Mentalino (who has a heart condition) via a surplus of hot sauce. It backfires (which is really an inadvertent success for Harry and Lloyd's lifespans), and Mentalino dies. Again, it takes Harry and Lloyd a while to figure this out.
16 Derick "Chubbs" Peterson in Happy Gilmore (1996)
Happy Gilmore holds a fair claim to Adam Sandler's most beloved movie. Part of the reason for its charming, Sunday afternoon movie vibe is the presence of Carl Weathers as Gilmore's instructor: Derick "Chubbs" Peterson.
Sandler's volatile ice hockey player turned volatile and unenthused (but successful) golfer needed a specific type of coach, and gator fight survivor "Chubbs" is just the ticket. Unfortunately, Gilmore underestimates the impact of "Chubbs" seeing the gator again (even if it is very much dead), and Weathers' character tumbles out the window. But, not out of the narrative, because his death pushes Gilmore further towards where he needs to be to take down one of cinema's worst humans: Shooter McGavin. Also, he pops up in Happy's "Happy Place."
15 Donny Kerabatsos in The Big Lebowski (1998)
Should there ever be a sequel to the Coen brothers' The Big Lebowski, there better be a role for Donny's ghost. Steve Buscemi worked with the sibling auteurs five times throughout the '90s, to increasing success. After small roles in Miller's Crossing, Barton Fink, and The Hudsucker Proxy, Buscemi played a major part of 1996's Fargo as ill-fated kidnapper Carl Showalter.
Buscemi's death in that movie is pretty surprising, but not nearly as much as the swift offing of The Big Lebowski's infinitely more likable Theodore Donald "Donny" Kerabatsos. The poor guy just spends his days sitting in a smoky bowling alley getting screamed at by his friend Walter. His other buddy, The Dude, is much kinder, but his unwitting exploits also end up escalating things to the point Donny has a heart attack in the bowling alley's parking lot to the sight of three nihilistic techno-pop musicians turned extortionists.
14 Brint, Rufus, and Meekus in Zoolander (2001)
Released shortly in the wake of 9-11, Ben Stiller's hysterical and quotable Zoolander hit theaters at exactly the wrong time. But, unlike Zoolander 2, it was funny then, and it's funny now.
It's also the one movie brave enough to include a "freak gasoline fight accident." Derek Zoolander escapes this incident, and to his credit, he's the only one in his quartet who seems to know that lighting a cigarette while covered in gasoline is a not great idea.
13 Blue in Old School (2003)
Before he was bringing Joaquin Phoenix's gritty take on the Joker to life, Todd Phillips was helming the imminently rewatchable frat comedy Old School. Part of what makes Old School special is casting, with everyone from Vince Vaughn, Will Ferrell, and Luke Wilson to Entourage's Jeremy Piven and Perrey Reeves.
Then there's Patrick Cranshaw's Joseph "Blue" Pulaski, a mid-80s member of the fraternity hopefuls with just as much spirit as anyone else. He displays as much by hopping into the ring for some mud wrestling with a topless young woman. He doesn't win, in fact, he dies, but he sure dies happy.
12 Edward 'Ned' Plimpton in The Life Aquatic with Steve Zissou (2004)
The Life Aquatic with Steve Zissou is consistently deemed one of the lesser films to come from the brilliant mind of Wes Anderson. But, time has been fairly kind to it, and the film does contain a likable cast of characters.
This includes the titular oceanographer Steve Zissou (Bill Murray) and Owen Wilson's devoted fan of Zissou's show, Ned Plimpton. Plimpton sincerely believes Zissou to be his father (it's eventually revealed Zissou is sterile), and their growing bond helps carry the film right up until a helicopter crash, which takes Ned's life.
11 Chad Feldheimer in Burn After Reading (2008)
The Coen brothers aren't averse to including shocking deaths in their movies. But to include the most jarring end to the most likable character in their most lighthearted movie must be something of a stroke of genius. Burn After Reading is in and of itself something of a mixed bag, but without a doubt, Chad Feldheimer is one of the most iconic roles Brad Pitt has ever played.
Feldheimer is one of two gym employees who stumble upon a CIA analyst's memoir. Intellectually, they're not quite qualified to handle anything CIA-related, even if it is just a memoir, which Pitt's Feldheimer essentially proves by sneaking into the house of George Clooney's U.S. Marshal Harry Pfarrer. Once Pfarrer arrives home, Feldheimer hides in his bedroom closet and, upon being discovered by Pfarrer, is swiftly shot in the head. The scene's immediacy is legitimately jarring, especially given the likability of the character and performer bringing him to life.
10 Highsmith & Danson in The Other Guys (2010)
Back when Adam McKay and Will Ferrell worked together, they knew how to make magic. For example, The Other Guys, a movie that has a bigger surprise than Ferrell's character having been previously called 'Gator.' Considered by many to be one of Ferrell's best movies, the movie starts off strong by forcing the audience to compare the detective duos of Samuel L. Jackson's P.K. Highsmith and Dwayne Johnson's Danson with the desk-set combo of Ferrell's Allen Gamble and Mark Wahlberg's Terry Hoitz.
Then, just as swiftly and heroically as Jackson and Johnson's characters swooped into the narrative, they jump out of it. Playing "My Hero" by Foo Fighters as they jump off a roof like they're an overconfident Thelma and Louise is the icing on a hilarious cake, and quite possibly the film's funniest scene as a whole.
9 Libby in Super (2010)
Too dark for some but a memorable experience nonetheless, James Gunn's Super manages to have the most shocking moment in the director's history (though the opening of The Suicide Squad gives it a run for its money). The project actor Rainn Wilson wants to be remembered for (even over The Office), Super is about as clear a window into Gunn's mind and style as there is.
The film concludes with Wilson's Frank 'The Crimson Bolt' Darbo and Elliot Page's Libby (or 'Boltie') storming the ranch of criminal Jacques (Kevin Bacon). Darbo is torn apart by his wife's (Liv Tyler) leaving him, convincing himself that Jacques has kidnapped her rather than the simple truth she likes him (and his drugs) more than her married life. Eventually, Jacques goes down, but so does Libby, and it's jarringly early into the duo's storming the ranch. It's also very quick. They're out in a field and a few gunshots are heard, Darbo falls back from the impact of a bullet, collects himself, and looks over to see Libby with most of her head gone. It's horrifying and legitimately disturbing.
8 Tom Hanson and Doug Penhall in 21 Jump Street (2012)
Metro-Goldwyn-Mayer
Considering Johnny Depp left the 1980s comedy series 21 Jump Street after its fourth of five seasons, it didn't seem like his Officer Tom Hanson would ever come back. After all, film work was always too enticing and Edward Scissorhands immediately elevated his star power to the stratosphere.
But he pops up in Phil Lord and Christopher Miller's 2012 ingenious cinematic reboot (as does Peter DeLuise's Officer Doug Penhall), even if he spends most of his screentime dressed as a biker. So, when he reveals his true identity only to be swiftly shot through the neck, it's a swift one-two that almost makes the viewer question what just happened (and laugh because it did).
7 Yondu in Guardians of the Galaxy Vol. 2 (2017)
While many consider James Gunn's Guardians of the Galaxy Vol. 2 to be slightly inferior to its predecessor, there's an argument to be made that it's superior. The through line of Star-Lord's search for a father figure is a strong one, as is Kurt Russell's performance as Ego and, especially, Michael Rooker as Yondu Udonta.
Ego may have helped create Peter Quill, but Udonta is his true father; The one who's guided him through life, taught him lessons, and helped him not get eaten a few times. So, when he dies heroically at the close of Gunn's sequel, it's both heartbreaking and a little surprising such a likable character would get offed.
6 Rosie Betzler in Jojo Rabbit (2019)
Taika Waititi's critically praised Jojo Rabbit has as fair a claim to the title of the director's best film as Thor: Ragnarok, and it even manages to carry a bigger surprise than any in that MCU film. Namely, Scarlett Johansson's Rosie Betzler (the title character's mother) dies. This was the second surprising death for a Johansson character in a single year, given Black Widow's fall in Avengers: Endgame.
Johansson's Rosie Betzler is a German anti-Nazi spy who specializes in transmitting messages. Unfortunately, this ends up getting her hanged. Even worse, her body is discovered (along with the audience) by her son. Fortunately for the audience, this is revealed only via a tasteful shot of her feet. But it's a devastating moment even without the full visual and stands as one of the narrative's most important moments.
5 Cassie Thomas in Promising Young Woman (2020)
One of the most important films of the last decade, Promising Young Woman is a gut-punch of a film fueled by dazzling work from Carey Mulligan as Cassie Thomas. It's a timely revenge film about chauvinism and rigged systems, where women's abuse is swept under the rug and the rug is never seen again.
But some men went too far with Thomas' friend, and she's systematically going to dismantle their lives. She knows this might cost her life, yet she goes through with it until her prognostication comes true. But, she has a contingency plan for her death, and the people who should finally go down do go down.
4 Colonel Rick Flag in The Suicide Squad (2021)
James Gunn's hilarious and violent The Suicide Squad stands as one of the auteur's best projects, if not his very best. The film starts off surprising, introducing a team of characters populated with familiar faces Suicide Squad (Margot Robbie's Harley Quinn and Jai Courtney's Captain Boomerang) and Gunn's other films (e.g. Nathan Fillion), then brutally kills off all but Harley.
Then, the narrative switches over to Amanda Waller's backup team, including the first film's Colonel Rick Flag (Joel Kinnaman). There's also John Cena's Peacemaker, who views Flag as an idol. The viewer figures if Gunn is going to kill off either Harley or Flag, it's going to be Flag, but they probably don't see it being Peacemaker as the one holding the bloody shard of glass.
One of the best dark comedies to hit the big screen in a while, The Menu's ingredients are pretty stellar from front to back. It's a movie to enter completely fresh, fully unaware of plot points or character details. The script by Will Tracy and Late Night With Seth Meyers' Seth Reiss is top-notch as is the ensemble cast, consisting of Anya Taylor-Joy, Ralph Fiennes, John Leguizamo, and Nicholas Hoult. The latter portrays self-proclaimed foodie Tyler Ledford. But, really, he's just a class-A jerk, which is precisely how he acts toward his date, Taylor-Joy's Margot Mills.
It's revealed that Margot is really an escort named Erin, and her date has been informed that every guest at the dinner will be dead by the end of the night. Slowik is impressed neither with Ledford's proven loudmouth nor his equally proven utter lack of talent. Ledford doesn't take his idol's opinion well and hangs himself. Much of the darkly comedic film is a surprise, but having one of the film's biggest (and usually very likable) performers portraying a truly pathetic monster is an effective twist, as is his shockingly early departure from the movie.
2 Michael Cera in This Is the End (2013)
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Sony Pictures Releasing
This Is the End is full of surprises and, really, it's a pretty impressive directorial debut for Seth Rogen and Evan Goldberg. It's a comedy that takes risks, goes places others haven't (at least not to the same extent), and satirizes Rosemary's Baby in a way that no other movie could.
But what makes it work well for fans is the cast's ability to take their public personas and warp them. Everyone is pretty close to their real-life persona (at least how the layperson viewer imagines them in real life), with a few notable exceptions. The first of these exceptions to rear his coked-out head is Michael Cera, who hilariously plays his part to the moon and dies pretty much immediately into the apocalypse via a light pole through the chest.
1 M. Gustave in The Grand Budapest Hotel (2014)
The Grand Budapest Hotel could very well go down as Wes Anderson's magnum opus, even including The Royal Tenenbaums and Rushmore. For a director who collects such talented ensembles, it's no small compliment to call the cast of Anderson's hotel-set comedy impressive, and everyone is clearly having fun in their roles.
Ralph Fiennes leads the film as the Grand Budapest's longtime concierge M. Gustave, but it's Zero Moustafa who tells Gustave's tale. Specifically, an older version of Zero, and it's not as if Gustave is by his side, so the audience knows that the decades older Gustave has passed. But, they don't know when or how, and the movie's answer is devastating. Gustave sacrifices himself standing between some soldiers and Zero (and Zero's new wife), and while it's a suitable finale for such a likable character, it's a tear-jerker nonetheless.
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