30 Comedy Movies With Some Of The Saddest Endings

These movies are guaranteed to make you laugh AND cry

Kylin

• Published in Film & TV
• January 31, 2023

Everyone has their own favorite genre of movie, it’s just part of having your own personal tastes. But there’s no arguing that comedies are definitely in the top 3 movie genres worldwide.

There’s something comforting about going into a movie theater knowing the new 90+ minutes are designed to make you feel good and laugh. A sort of well-deserved break from the stressors of life.

Comedy movies especially seem to permeate our culture. So many fun one-liners or involved quotes have become so embedded that you could recognize the context without ever seeing the movie itself (“Yeah, well, you know, that's just, like, your opinion, man.”).

And when all is said and done with a comedy movie, one would expect to be left feeling some sort of satisfaction from a happy ending. Unless you’re caught off guard by an ending that’s not so happy.

After all, being faced with a bit of sadness can really help one appreciate joyful and silly moments. I think that’s why some of the most acclaimed comedic movies tend to have significant moments of turmoil and sadness or endings that are really emotional.

We put together a list of 30 movies that would be considered “comedies,” but also feature that gut punch of a moving and emotional ending. Keep scrolling to see what made the list, why, and the trailer for each movie.

Get cozy and grab some popcorn

1. P.S. I Love You

A classic rom-com that literally makes me sob every time I watch it. We follow Hilary Swank as Holly Kennedy after she loses her husband and the love of her life, Gerry, played by Gerard Butler.

Gerry knew he wasn't going to survive his illness and made plans prior to his passing to help Holly cope with her loss. Starting on her 30th birthday, she starts receiving letters from him that end up inspiring her to start fresh.

Watch the trailer for P.S. I Love You below

2. Superbad

This movie can hit close to home if you've ever experienced a close friend move away after high school. While yeah, it can definitely be considered a "crude comedy," Superbad actually has significant themes about friendship.

While the premise may be based on two best friends trying to lose their virginity before going to college, we get to watch two close friends grow into their selves. They face and overcome their anxiety of growing apart from one another and being alone.

Watch the trailer for Superbad below

3. (500) Days Of Summer

One of the shining examples of the Manic Pixie Dream Girl tropes, (500) Days Of Summer is still a fun rom-com. We follow a hopeless romantic, Tom, played by Joseph Gordon-Levitt as he thinks back over the relationship he had with Summer, played by Zooey Deschanel after she suddenly breaks up with him.

While going through the past 500 days he spent with Summer, he is able to rediscover his passions in life.

Watch the trailer for (500) Days of Summer below

4. Young Adult

In Young Adult, we follow a very self-absorbed young adult author Mavis Gary, played by Charlize Theron, as she returns to her hometown and tries to steal her high school boyfriend from his wife and child. Although the story may lead you to believe things will turn out nicely, things end up going awry.

But during her travels, Mavis starts to become more self-aware and finds herself in an unusual relationship with a former classmate, Matt Freehauf, played by Patton Oswalt. For a brief moment, it seems as though she unintentionally stumbled into a healthy relationship, one that helps her develop into a decent, empathic person.

Watch the trailer for Young Adult below

5. Chasing Amy

Kevin Smith perfectly captures the feelings of insecurity, jealousy, and even those feelings of inadequacy that can develop from dating someone who has more dating experience than you in Smith's very funny third film set in the View Askewniverse.

Watch the trailer for Chasing Amy below

6. In Bruges

Hitmen, Ray, played by Colin Farrel, and Ken, played by Brendan Gleeson hide out in Bruges, Belgium after a challenging job goes tragically wrong. Ken falls in love with the city, while Ray despises it.

Their experiences and encounters with the locals and other tourists make their lives even more bizarre. All before the climax of a very sad ending.

Watch the trailer for In Bruges below

7. Hot Rod

For a very silly and somewhat simple plot, Hot Rod actually has a lot of heart to it. With the ultimate goal to earn enough money to pay for his stepfather's heart surgery (so he can beat him up to prove he's man enough) Rod Kimble, played by Andy Samberg, is a want-to-be stuntman who risks his life performing stunts.

Rod ends up setting a new record for a motorbike leap, in which he proves to himself that he is "man enough" to achieve his goals in spite of what Frank thinks/says and without Frank's help.

Watch the trailer for Hot Rod below

8. Dr. Strangelove

One of the most famous political satire films, Dr. Strangelove was a parody of the Cold War as it was still ongoing. The end of all life on Earth from nuclear war marks the film's grim ending.  

Watch the trailer for Dr. Strangelove below

9. The Circus

The Circus is a 1928 silent film that features some of Charlie Chaplin's funniest slapstick physical humor, but also one of the most unexpectedly depressing endings in his filmography. The unexpected melancholic finale still manages to hold it's own over 90 years later.

Watch the trailer for The Circus below

10. Don't Look Up

The satirical movie Don't Look Up seems to hit pretty close to how things feel these days. Two scientists do everything they possibly can to warn the public of a comet heading toward the Earth, that would have potentially fatal consequences, but no one seems to care.

Watch the trailer for Don't Look Up below

11. Mrs. Doubtfire

The classic Robin Williams film Mrs. Doubtfire is full of hilarious antics as Williams pretends to be an elderly British woman in order to be hired by his ex-wife as their children's Nanny following a contentious divorce that left him without custody. Although his ruse is eventually revealed, Mrs. Doubtfire does improve his children's (and ex-wife's) lives by staying on full-time.

While they do not get back together, both were able to learn from the experience, Williams' character especially.

Watch the trailer for Mrs. Doubtfire below

12. The Grand Budapest Hotel

Wes Anderson is well known for directing incredible tragic comedies that gracefully maintain a tonal balance that will make you laugh, but also have parts that pull the heartstrings in such a way that will make you cry. The Grand Budapest Hotel is no exception.

Watch the trailer for The Grand Budapest Hotel below

13. Planes, Trains and Automobiles

A classic comedy starring some of the comedic heavy-hitters at the time, Steve Martin and the late John Candy. It could be argued that Planes, Trains and Automobiles was one of the founding "improbably buddy road-trip" movies, inspiring a whole new comedic genre.

The overall message is obviously that no one should have to spend the holidays alone. At the end of the movie, Steve Martin's character Neal reflects on his (less-than-relaxing) time with John Candy's character Del and realizes that Del is alone.

Neal rushes out to find Del, and Del ends up joining Neal and his family for Thanksgiving. While the movie may spend a lot of the time being very silly and full of ridiculous things, the ending is really touching.

Watch the trailer for Planes, Trains And Automobiles below

14. Marley & Me

If you're not familiar with Marley & Me, the family comedy centered around a very sweet, loveable albeit mischievous dog, you should be sure to have a box of tissues handy when you go to watch it. As in many movies about a pet's life, it ends with the titular Marley being euthanized after suffering the sudden and fatal condition gastric dilatation volvulus.

Watch the trailer for Marley & Me below

15. American Graffiti

A groundbreaking teen comedy follows a group of soon-to-be college freshmen on their last day together before everyone moves on to college. The ending discloses that two of the characters were in a fatal car crash, while another went missing in Vietnam.

Watch the trailer for American Graffiti below

16. 50/50

50/50 is a witty comedy about the highs and lows of friendship, with the depressing twist that one of the characters gets diagnosed with terminal cancer.

Watch the trailer for 50/50 below

17. Guardians Of The Galaxy Vol. 2

While the first Guardians of the Galaxy had its own intense emotional moments, Vol. 2 ends with Yondu's funeral. Yondu was an important part of Peter Quill's life, as he was a surrogate father figure for him.

Watch the trailer for Guardians Of The Galaxy Vol. 2 below

18. Instructions Not Included

This 2013 Mexican comedy was translated into countless languages and beloved across the globe and became the highest-grossing film in Mexican history. Following Valentín Bravo, played by Eugenio Derbez, a local playboy who ends up forced to care for his baby daughter after an ex-lover dropped her off at his doorstep and left.

Valentín, inspired and motivated by having to care for his daughter, Maggie, crosses the border from Mexico to America and ends up being hired as a stuntman. He raises Maggie for 6 years before finding himself in a custody battle with her mother.

The movie ends with a surprising and devastating twist, that Maggie is terminally ill. This is yet another comedic movie that ends with complete heartbreak.

Watch the trailer for Instructions Not Included below

19. Meet The Parents

This comedy follows Greg Focker, played by Ben Stiller, as he meets his girlfriend Pam's (played by Teri Polo) parents for the first time, with the intention of proposing to her in front of her family. Robert De Niro plays Pam's father, Jack, an ex-CIA agent who interrogated double agents, and made Greg's life as difficult as possible.

After enduring psychological torture from Jack for nearly the entire film, Greg gives up and leaves to catch the next flight home. Realizing he had driven away a great man that his daughter really loves, Jack rushes to fix things with Greg at the airport.

In a touching scene, Jack asks Greg to be his son-in-law, turning the film from a terrifying in-law fever dream into a heartwarming acceptance of families.

Watch the trailer for Meet the Parents below

20. Harold And Maude

A cult classic black comedy, starring Ruth Gordon as an eccentric 79-year-old, and Bud Cort as a dead-pan disillusioned 19-year-old who is intrigued with death. Cort meets Gorden at a random person's funeral and the two develop a friendship, which eventually turned into a taboo romantic relationship.

Watch the trailer for Harold and Maude below

21. Tommy Boy

Tommy Boy isn't just any other buddy adventure comedy. Instead, there's an emotional undercurrent about expectations and parenthood that continue to build to the climax.

Chris Farley plays Tommy Callahan, the son of Thomas R. "Big Tom" Callahan Jr. who owned the family's auto parts plant Callahan Auto, and David Spade plays Richard Hayden, the scornful assistant to Big Tom.

After Big Tom's sudden and unexpected death, Tommy and Richard embark on a mission to sell enough brake pads to save the family business. They travel through hell and back, but ultimately succeed in saving the business.

The movie ends with Tommy, alone on a boat, reflecting on finally accomplishing something to feel more connected to his late father, and acknowledging that all he was doing was trying to live up to his father, whom he deeply loves and misses.

Watch the trailer for Tommy Boy below

22. When Harry Met Sally

This famous rom-com follows the lives of Harry, played by Billy Crystal, and Sally, played by Meg Ryan, as they continuously run into each other throughout their lives. While their bond may be obvious from the get-go, their relationship was contentious at the start.

After years of the passive-aggressive/will-they-wont-they sort of tension, Harry accepts his feelings and surprises Sally at a New Year's Eve party. He shares all the things he adores about her in a timeless romantic monologue.

Watch the trailer for When Harry Met Sally below

23. Roman Holiday

A true classic, the Roman Holiday is a 1950's rom-com starring Audrey Hepburn as a European princess, and Gregory Peck as an American newspaper reporter. The two spend the majority of the movie lying to one another before they realize they're soulmates.

Unfortunately, they cannot be together, with Hepburn returning to her royal duties along with her newfound sense of independence over her life. The movie ends with the two saying goodbye, with Peck leaving on his own as Hepburn returns to her native country.

Watch the trailer for Roman Holiday below

24. Life Is Beautiful

This Italian dramedy is set in 1939 fascist Italy and tells the story of a father who does everything he can to protect his son from the horrors of internment in a Nazi concentration camp. Before finding out the heartbreaking outcome of the main character, Roberto Benigni's talent and skillful physical comedy shine through the movie.

Watch the trailer for Life Is Beautiful below

25. Seeking A Friend For The End Of The World

This apocalyptic rom-com/road trip movie stars Steve Carell and Keira Knightley who play neighbors that end up forming an unexpected bond shortly after learning the world is set to end in a few short weeks as an asteroid was discovered on a fatal collision course towards Earth.

During the final few minutes of the film, Knightley and Carell lay together in bed, talking to distract themselves from the inevitable, with the sounds of the asteroid hitting in the background. Knightley's character says, "I thought that somehow we'd save each other," to which Carell's character answers, "We did."

The two are comforted in each other's embrace as a bright light pours over them, and the movie closes.

Watch the trailer for Seeking A Friend For The End Of The World below

26. Love Actually

The classic Christmas rom-com has multiple endings, which makes sense given the movie follows roughly a dozen different and intertwining stories. A few of the stories don't have a comfortable, easy conclusion, unlike the majority of the stories that end with the characters finding love and happiness.

Like the subplot about the unhappy marriage between Harry and Karen (played by Alan Rickman and Emma Thompson), and the coworkers Sarah and Karl (played by Laura Linney and Rodrigo Santoro) who end up having unrequited affections.

In the first subplot, Karen finds out her husband, Harry, is having an affair. The other, Sarah is about to allow herself to give in to her long-time crush on her coworker, only to have her plans dashed by needing to help care for her mentally ill brother, eventually choosing to put her family's needs above her own love life.

Watch the trailer for Love Actually below

27. The Big Lebowski

The iconic movie The Big Lebowski is as funny as it is beloved. The movie has a moving and unforgettable scene at the end where Jeffrey Lebowski/The Dude, played by Jeff Bridges, and Walter, played by John Goodman, spread their friend Donny's ashes over an oceanside cliff.

Watch the trailer for Instructions The Big Lebowski below

28. Napoleon Dynamite

A lot of folks missed the significance of Napoleon Dynamite. While criticized for having no plot, it's more about how someone like Napoleon, played by Josh Heder, moves through life.

His character has painful social awkwardness (suspected that maybe the character is autistic), and the audience has a front-row view of how difficult it is for him to follow through with typical high school tasks like attending prom or performing in a talent show. It makes the ending even better when he realizes he's happier doing things he likes instead of trying to conform to what others think he should do to have a "normal" life.

Watch the trailer for Napoleon Dynamite below

29. The Break-Up

While the name of the movie gets straight to the point, most viewers likely anticipated this rom-com would end with the couple, played by Jennifer Aniston and Vince Vaughn, would reconcile and getting back together. Instead, their characters continue to grow apart and estranged from each other as the movie progresses, ending with both alone.

During the ending scene, the two find themselves in a surprise encounter, stoking the hopes for a last-minute reunion, instead, they wish each other well and continue on their separate ways. While not tragic or disturbing, it is more melancholic than other battle-of-the-sexes rom-coms.

Watch the trailer for The Break-Up below

30. Intouchables

The film focuses on the unlikely friendship that forms between an older, wealthy quadriplegic and his younger, ex-con caretaker, and their hilarious and heartwarming escapades. The movie ends with a photo of the two real people that inspired the movie.

Watch the trailer for Intouchables below

The combo of funny and sad can be as satisfying as having a snack that’s both salty and sweet. The contradicting hit to your senses (or in this case, your emotions) really adds a depth of enjoyment you didn’t know you wanted.

Did your favorite comedy make this list? Or did we miss an opportunity to include a movie that hit the marks of “comedic but also sad”?

Let us know your thoughts in the comments section below.

Kylin