Some people hate the term “dramedy.” They would rather have a film that’s either funny or dramatic and not both. But on the contrary, there are plenty of films that can go both ways and actually be great. Many of these films came from the early 21st century, succeeding in the indie world and garnered plenty of acclaim from critics and audiences. The ones that were R-rated were especially memorable given the boundaries they were able to push.
While the R-rated dramedy has obviously been around longer than the 2000s, the ones released during that decade have resonated strongly with today’s audiences for many reasons; nostalgia, inspiration, or just pure viewing pleasure. They were able to test the limits of what can make us laugh or cry or both.Many of these films have delivered profoundly heartfelt moments while being naturally funny. These can often be the testaments of what true filmmaking can do, with the right balancing tone. So, which 2000s dramedies are considered the best?
10’Funny People' (2009)
Directed by Judd Apatow
Funny Peopleis the third directorial effort ofJudd Apatow. Unlike his hit straight comediesThe 40-Year-Old VirginandKnocked Up, this one took a more dramatic route and dealt with more serious subject matter than covered in his films. George Simmons (Adam Sandler) is a retired standup comedian who learns he has leukemia. Already depressed with his life, Simmons returns to his standup roots and meets a struggling comic named Ira (Seth Rogen), whom he hires as an assistant to help him write jokes and cope with the little time he has left.
Originally receiving a mixed response from critics, bombing at the box office,Funny Peoplewas criticized for its length, lack of humor, and the direction it takes halfway when Simmons learns he has beaten his disease. But it deserves re-appraisal;despite Sandller essentially playing a washed-up version of himself, it remains one of the best performances of his career. He manages to skillfully capturelearning how to improve both his professional and personal liveswhile dealing with the frustration of his mistakes and potential death.Funny Peopledoesn’t have all the funny, but it does stay grounded in real people problems.
Funny People
9’In Bruges' (2008)
Directed by Martin McDonagh
Irish-English writerMartin McDonaghis considered to be a specialist in dark comedies; his ability to craft humorous scenarios with brutal bouts of violence in his writing has been highly praised in the worlds of theater and film. His first feature wasIn Bruges, released in 2008 and received critical acclaim as an unapologetically dark comedy/thriller. It starsColin Farrellas Ray andBrendan Gleesonas Ken, two hitmen who are ordered by their boss Harry (Ralph Fiennes) to remain in the Dutch city of Bruges after a botched job. During that time, they take in the sights of the city until everything begins to unravel.
What McDonagh did was craft a highly entertaining crime thriller filled with witty dialogue reminiscent of the works ofDavid MametandQuentin Tarantinoand atop-notch dynamic between Farrell and Gleeson; the former ended up winning a Golden Globe for Best Actor in a Comedy or Musical. Everybody in the cast, including Fiennes, delivers sharp performances filled with hilarious banter and plenty of curse words to go. McDonagh’s style of dark comedy would carry on into his following films, includingThe Banshees of Inisherin(2022) which reunited him with Farrell and Gleeson.In Brugesis highly entertaining for anyone who loves dark comedy.
8’Punch-Drunk Love' (2002)
Directed by Paul Thomas Anderson
In 2002,Adam Sandlerstarred in three films. The first two wereMr. DeedsandEight Crazy Nights, which were both pretty on-brand for Sandler’s style of comedy. But moviegoers were taken by surprise withSandler’s third 2002 film, a dramedy calledPunch-Drunk Love, by acclaimed directorPaul Thomas Anderson. It was hisfirst dramatic role and often considered to be one of his best films, even landing him a nomination for Best Actor in a Comedy or Musical at the Golden Globes.
Sandler plays Barry Egan, a socially-awkward business owner in the San Fernando Valley who falls in love with Lena (Emily Watson). But along the way, he has to deal with his berating sisters and an extortionist from a phone sex hotline. The filmemploys many of the themes commonly found in Anderson’s work such as lonely protagonists winding up in desperate situations. But ultimately, whatPunch-Drunk Loveis about is falling in love and how good it feels. Sandler brilliantly sells Barry as someone who just needs a break, which leads to dramatic and comedic situations that deserve to be appreciated.
Punch-Drunk Love
7’Adaptation' (2002)
Directed by Spike Jonze
Have you ever been so frustrated with writing a movie adaptation of a famous book that you end up writing the screenplay about the adaptation process instead? That’s what happened with screenwriterCharlie Kaufman. From directorSpike Jonze,Adaptationcenters aroundNicolas Cageplaying a self-loathing Kaufman as he struggles to adapt the non-fiction bookThe Orchid ThiefbySusan Orlean—all while dealing with his twin brother Robert (also played by Cage) who wishes to become a screenwriter. That plot also intertwines with Orlean (Meryl Streep) and her journey writing about the orchid thief himself, horticulturist John Laroche (Chris Cooper).
Adaptationreceived critical acclaim for its screenplay and performances, and even won Cooper the Oscar for Best Supporting Actor. While several of the real life events are highly exaggerated, the film mainly excels with its portrayal of the struggles of writing;how to please your audience, how to not be derivative, and how emotions can influence your decisions. These are all common elements in self-reflection and identity crises, which are big themes in the works of Kaufman, as previously demonstrated in 1999’sBeing John Malkovich.Adaptationis not only a great dramedy, but also highly inventive and a wildly original piece of metafiction.
Adaptation.
6’Thank You for Smoking' (2005)
Directed by Jason Reitman
Jason Reitman—son of the late directorIvan Reitman—has made a career of directing films about flawed protagonists, starting with his 2005 debutThank You for Smoking.Aaron Eckhartstars as Nick Naylor, a lobbyist for Big Tobacco who loves his job and will do anything to fight for the American right to smoke cigarettes—but also must be a good role model for his son Joey (Cameron Bright). The dramedy also boasts a strong ensemble cast consisting ofKatie Holmes,J.K. Simmons,Maria Bello,David Koechner,Rob Lowe, andRobert Duvall.
The film was praised for being a sharp satire of the tobacco industry, corporate responsibility, and the politics of social issues. The marriage of thesharp writing and Eckhart’s charismatic performance is what elevatesThank You for Smokinginto a darkly hilarious piece rather than what could have easily been a mean-spirited and sophomoric dud of a film.Thank You for Smokingrevels in wit and irony while not treating its audience disrespectfully, andremembers to be funny while also making a point.
Thank You For Smoking
Nick Naylor, the eloquent and persuasive spokesperson for the Academy of Tobacco Studies, dedicates his career to defending the interests of the tobacco industry. His talent for spinning arguments and manipulating the media makes him a formidable advocate for smokers' rights. However, as he juggles his controversial career and the challenges of fatherhood, Nick faces increasing scrutiny from health advocates and government officials.
5’Happy-Go-Lucky' (2008)
Directed by Mike Nichols
There have been many chronically optimistic characters in media like Buddy fromElf, Leslie Knope fromParks and Recreation, and Ted Lasso, to name a few. But none are as happy-go-lucky as Poppy fromHappy-Go-Lucky. This 2008 British film by directorMike NicholsstarsSally Hawkinsin a Golden Globe-winning performance as an English schoolteacher who is eternally cheerful and upbeat towards everyone in her life, including her pessimistic driving instructor Scott (Eddie Marsan).
Much of the conflict comes from Scott’s frustration at Poppy’s optimism being mistaken for incompetence, butHappy-Go-Luckyhas less of a central plot and is more of a slice-of-life piece. Through its pacing and naturalistic tone, the film allows us to enjoy aspects of Poppy’s life, like being a good teacher, enjoying quality time with friends and family, and even finding love. A lot of it comes from Hawkins’s amazing performance, as you either grow to love or hate Poppy.While she cannot make everybody happy, at least Poppy can live with being happy herself.
Happy-Go-Lucky
4’Little Miss Sunshine' (2006)
Directed by Jonathan Dayton and Valerie Faris
One of the most memorable scenes of 2000s indie cinema comes fromLittle Miss Sunshine, when the Hoover family is rushing to get into their yellow Volkswagen van. It’s one of those images where, if seen in the form of a silhouette, it will be recognized immediately. From directing teamJonathan DaytonandValerie Faris,Little Miss Sunshinetells the story of a dysfunctional family in a race to get their daughter to a beauty pageant. It was a big success in 2006, earning two Oscars forMichael Arndtfor Best Original Screenplay andthe lateAlan Arkinfor Best Supporting Actor.
Much of what madeLittle Miss Sunshinework came from two crucial elements: the writing, which came from a balance of quirky character moments rather than big gags and punchlines for comedy, and the strong cast. Alongside Arkin,Greg Kinnear,Toni Collette,Steve Carell,Paul Dano,and the Oscar-nominatedAbigail Breslindeliver moment upon moment that, despite the many character flaws, make audiences root for them. The tragedy of the Hoovers is their lack of any major wins, butthe heart ofLittle Miss Sunshinestems from overcoming their insecurities and learning to win together, even if it means reaching a children’s beauty pageant on time.
Little Miss Sunshine
3’Up in the Air' (2009)
The late 2000s was a period of economic hardship due to the worldwide recession, and no other film at that time best reflected it asUp in the Airdid.George Clooneydelivers one of the best performances of his careeras Ryan Bingham, a man whose job is to fly across the United States and fire people on behalf of their companies. He also enjoys solitary living, making as few connections as possible. But along the way, Ryan falls for fellow frequent flier Alex (Vera Farmigia), becomes a mentor to his younger coworker Natalie (Anna Kendrick), and finds his job threatened by new technology.
Coming off the success ofJuno, directorJason Reitmandelivered another great dramedy about sympathizing with a complicated figure, much like whatThank You for Smokingwas. Because Ryan is faced with many different conflicts with his work and way of living, he actually begins questioning his own life philosophy. WhileUp in the Airalso follows the beats of a romantic comedy, it throws in some twists to stand out, all while brilliantly using the recession as the backdrop. The comedic moments come from the terrific performances and the drama stems from theunfortunately familiar feelings during that difficult time in the late 2000s.Up in the Airexcels at being about making connections during disconnected times.
2’Almost Famous' (2000)
Directed by Cameron Crowe
When it comes to having a favoriteCameron Crowefilm, it’s usually narrowed down to two choices:Jerry MaguireorAlmost Famous. The latter is an early 2000s release and often considered to be one of the best dramedies of the decade. Set mostly in 1973,Almost Famouscenters around introverted teenager William Miller (Patrick Fugit) recruited byRolling StoneMagazine to write a cover story about the rock band Stillwater. He joins the band as they go on tour and grows close with them, as well as groupie Penny Lane (Kate Hudson).The film is semi-autobiographical, based on Crowe’s own experiences writing forRolling Stone.
Despite its disappointing box office results,Almost Famouswas one of the most critically acclaimed films of 2000, with praise going towards both its naturally comedic and heartwarming moments and the performances of the cast, particularly Hudson andFrances McDormandas William’s mother Elaine; both received Oscar nominations for Best Supporting Actress. The film was also a great portrayal of the rock scene in the early ‘70s; in such a complicated decade, there’s stillwarmth found in the joy of camaraderie and the music, inviting viewers to take in the journey with nostalgia. With Crowe making it his most personal film,Almost Famousis irresistible in its charm.
Almost Famous
1’Sideways' (2004)
Directed by Alexander Payne
Nearly two decades beforeThe Holdoversbecame an awards season hit, directorAlexander PayneandPaul Giamattiworked together onSideways, another critical darling and one of the best films of 2004. Giamatti stars as Miles, a depressed, struggling writer who takes his carefree best friend Jack (Thomas Haden Church) on a road trip to Santa Barbara wine country before Jack’s upcoming wedding. Miles wants to relax and teach Jack how to appreciate wine, but Jack is in search of an affair, leading them to meet Stephanie (Sandra Oh) and Maya (Virginia Madsen). From there, it spirals into a trip of self-reflection and hijinks as the two men deal with their own mid-life crises.
Originally adapted from the novel of the same name byRex Pickett,Sidewaysworks in the best ways; it feels the most human of all the dramedies of the 2000s.Miles and Jack are such polar opposites and yet their friendship is easily believable. The film also turned Giamatti and Haden Church from recognizable character actors to A-listers, and even won Payne and co-writerJim Taylorthe Oscars for Best Adapted Screenplay. While it didn’t win Best Picture,Sidewayswon plenty of acclaim as one of the best films of the decade, as well as the best R-rated dramedy due to its rewatchability, great balance between humorous and heartbreaking, and refreshingly relaxing tone.It’s like enjoying a glass of fine wine, and once it’s over, you’ll want more.
