Dying is easy; comedy is hard, and laughing through the pain is even harder. However, Hollywood is an expert at finding humor in the drama; thus, the comedy-drama sub-genre was born. Also known as “dramedy,” this peculiar sub-genre has produced some of the best and most memorable pictures in Hollywood history, many of which have come out this century.
From sweet explorations about family to biting character studies on complicated men, these dramedies represent the best of the 21st century. Audiences may laugh, cry, or do both, but they surely won’t forget about these wonderful movies that masterfully balance comedy and drama.

10’Tully' (2018)
The trio ofJason Reitman,Diablo Cody, andCharlize Theronproduced two modern dramedies on their way to becoming classics. However, 2018’sTullymight be the best, with Theron delivering one of her most compelling performances. The film follows the unlikely friendship between Marlo, an over-stressed mother of three, and Tully, her night nanny.
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Anchored by Theron’s vulnerable performance and powered by Cody’s razor-sharp screenplay,Tullyis an honest and nuanced portrayal of the struggles and joys of parenthood. Funny, witty, and offering some intriguing insights into a well-known subject,Tullybrings the best out of everyone involved.
9’Captain Fantastic' (2016)
The offbeatCaptain FantasticstarsViggo Mortensenin one of his most refreshing performances. The actor plays Ben Cash, a man living in isolation with his wife and children for a decade. Unforeseen circumstances force the family to reintegrate into society, causing a culture clash in their tight-knit dynamic.
Quirky but clever,Captain Fantasticis a celebration of familythat excels as a commentary on modern society and a showcase for Mortensen’s comedic abilities. While the plot is nothing out of the ordinary,Captain Fantasticfeels unique and worthwhile thanks to a combination of gravitas and honesty, using its premise to offer intriguing insights into familial dynamics and the importance of challenging conventions.

8’About a Boy' (2002)
Hugh Grantarguably delivers his best performance in the 2002 dramedyAbout A Boy.The film centers on Will, a selfish and irresponsible womanizer who develops a unique bond with Marcus, an eccentric twelve-year-old played byNicholas Hoult.Toni ColletteandRachel Weiszalso star.
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Based on the eponymous novel by Nick Hornby,About a Boyis the perfect vehicle for Grant’s acting sensibilities. Abandoning his usual bulbing shtick, Grant delivers a layered portrayal of shallowness concealing genuine pathos. Perfectly complemented by Hoult’s fresh, offbeat performance, Grant elevatesAbout a Boy, turning it into one of the most surprising and rewarding dramedies of the noughties.
7’Up in the Air' (2009)
Jason Reitman directs one ofGeorge Clooney’s finest performancesin the 2009 comedy-dramaUp in the Air. The film centers on Ryan Bingham, a traveling downsizer whose erratic and carefree way of life is challenged by an ambitious young woman’s proposal. Faced with a shot at something real with a fellow frequent flier, Ryan must decide what he wants from his life.
Up in the Airis among Reitman’s most humane films. Deftly balancing comedy with drama, Reitman brings out the best in Clooney and his equally stellar co-stars,Vera FarmigaandAnna Kendrick. Offering a poignant critique of corporate America,Up in the Airis a fascinating exploration of love, relationships, ambition, and fulfillment.

6’Frances Ha' (2012)
In the pantheon of great screenwriters capable of capturing the humor in tragedy, few outrankNoah Baumbach. The acclaimed director is behind many of the 21st century’s best dramedies, butFrances Hamight be the best. Baumbach’s significant other,Greta Gerwig, stars as the titular character, a struggling twenty-seven-year-old danger pursuing her dreams in New York.
Dizzy to the point of seeming aimless,Frances Hais an endearing and loving ode to the unpredictability of life,a coming-of-age story for adults. Strengthened by a stellar turn from Gerwig and Baumbach’s trademark empathy,Frances Hais a singular dramedy that will ring unbelievably true to millions of twenty-somethings.

5’Sideways' (2004)
Joining Baumbach in the line-up of incredible tragicomedy auteurs isacclaimed writer-directorand two-time Oscar winnerAlexander Payne. Known for his black humor and satirical explorations of Americana, Payne is a master of the dramedy, and his 2004 film,Sideways, might be his crowning achievement.Paul GiamattiandThomas Haden Churchstar as two past-their-prime forty-year-olds who take a road trip to Santa Barbara wine county.
A masterpiece of adult cinema,Sidewaysis a dry, funny, and intelligent look into adulthood and the dreams lost along the way. Full of Payne’s trademark compassion for the broken and dissatisfied,Sidewaysis warm and touching, a film that has aged as beautifully as the wines it celebrates.

4’A Serious Man' (2009)
TheCoensmight be best known for their crime films, but they have mastered multiple genres throughout their prolific career, including the notoriously thorny black comedy. Their 2009 black comedy-dramaA Serious ManstarsMichael Stuhlbargas a man struggling with his faith as his life crumbles around him.
Biting and quite relentless,A Serious Manis among the Coens' most mature and layered efforts. Although imperfect,A Serious Manwears its flaws with pride, using them to further complement its exploration of challenging themes like faith and purpose. With a spectacular performance from Michael Stuhlbarg and a tough screenplay that doesn’t settle for easy answers,A Serious Manis a one-of-a-kind entry into the Coens' filmography.
3’Adaptation' (2002)
The notoriously challengingCharlie Kauffmandelivered his most meta screenplay with 2002’sAdaptation.Nicolas Cagestars as a fictionalized version of Kauffman, also playing his fictitious twin brother, Donald, with the film chronicling Charlie’s struggle to adapt Susan Orlean’s non-fiction bookThe Orchid Thief.Meryl StreepandChris Cooperalso star.
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Bizarre and often pitiful,Adaptationis a truly odd yet fascinating exploration of the creative process. Cage, Streep, and Cooper deliver some of their best work as three - well, four - conflicted, aimless souls whose lives collide with unexpected results.Adaptationis a writer’s movie with a screenplay so daring and wildly original that it becomes instantly unforgettable.
2’Little Miss Sunshine' (2006)
Few tragicomedies are as memorable or effective as 2006’sLittle Miss Sunshine. A practically perfect ensemble, comprised ofGreg Kinnear, Toni Collette,Steve Carell,Alan Arkin,Paul Dano, andAbigail Breslin,star in a story about a dysfunctional family taking their youngest to a child beauty pageant.
Full of broken but endearing and profoundly sympathetic characters,Little Miss Sunshineis an exercise in melancholy disguised as a feel-good movie. The film is an enthusiastic and overt celebration of averageness, a passionate and warm rallying cry for those stuck in the middle. Funny and sentimental but never manipulative,Little Miss Sunshineis a tragicomedy that understands tragedy and humor often go hand-in-hand.
1’The Royal Tenenbaums' (2001)
Wes Andersoncemented his place as one of modern cinema’s most visually distinctive auteurs with his biting black comedyThe Royal Tenenbaums. A truly impressive ensemble gathers to tell the story of the Tenenbaums,a dysfunctional and awkward familywho find their way back to each other after their patriarch reveals he is dying.
Wickedly funny but emotionally poignant,The Royal Tenenbaumscarries itself with an overt playfulness that makes it irresistible. Using its carnival of top-notch performers to its fullest, the film is a quirky but mature and thought-provoking examination of family and legacy and the perfect proof that style and substance can not only co-exist but actually enhance each other under the right guidance.