20+ Best Ever Comedy Dramas
These films aren't just funny, they're funny and thought provoking. They have clever, witty dialogue, interesting characters and more than a few unforgettable scenes. Well that's my opinion anyway. I've tried to only include movies that portray ostensibly "real" characters who occasionally do or say funny things or fall into comedic situations as opposed to outright no-holds-barred comedy. This is why you won't find anything with Adam Sandler, Jim Carrie or Will Ferrell here although much of their stuff is undeniably hilarious.
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- DirectorRob ReinerStarsBilly CrystalMeg RyanCarrie FisherHarry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.Great characters, extremely funny dialog and who can forget Sally's Orgasm act in the diner. The chemistry between Meg Ryan and Billy Crystal is magical and New York is an amazing backdrop. Great script, superb acting, beautiful score and flawless directing. My unabashed number one favorite movie of all time.
- DirectorHarold RamisStarsBill MurrayAndie MacDowellChris ElliottA narcissistic, self-centered weatherman finds himself in a time loop on Groundhog Day.OK I may be stretching the definition of Drama here but this is one of my all time favorites so give me a little leeway. Bill Murray has never been more Bill Murrayish and Andy McDowell is beautifully shot in this hilarious tale that is at the end of the day all about personal growth. Chris Elliot gets to deadpan some great lines as well and the groundhog is superb. "Don't drive angry."
- DirectorAlexander PayneStarsPaul GiamattiThomas Haden ChurchVirginia MadsenTwo men reaching middle age with not much to show but disappointment embark on a week-long road trip through California's wine country, just as one is about to take a trip down the aisle.I love this movie. A lovable loser and a lovable scoundrel team up to create an irresistible "opposites attract" buddy movie. Virginia Marsden and Jackie Oh are fabulous in support and the California Wine country scenery is gorgeous. As for memorable scenes, there are few more beautiful speeches than the ones on the subject of wine appreciation given by Miles and Myra.
- DirectorDoug LimanStarsVince VaughnHeather GrahamJon FavreauA wannabe actor has a hard time moving on from a break-up, but he is lucky to have supportive friends.What a great flick. My favorite "Buddy" movie ever. So many memorable lines and hilarious scenes John Favreau and Vince Vaughn hit it out of the park. Favorite scene.. "You got these huge claws..."
- DirectorMike NicholsStarsDustin HoffmanAnne BancroftKatharine RossA disillusioned college graduate finds himself torn between his older lover and her daughter.An all-time classic dramatic comedy. An eager young Dustin Hoffman opposite sultry cougar Ann Bancroft and a beautiful young Katherine Ross and don't forget that amazing Simon and Garfunkle soundtrack. Movie magic.
- DirectorWayne KramerStarsWilliam H. MacyMaria BelloAlec BaldwinIn an old school Las Vegas casino, its top gambling jinx breaks his curse when he falls in love, much to his boss' consternation.If you haven't seen this flick yet and you are a fan of either Alec Baldwin or William H. Macy then what the heck are you waiting for? Go rent it right now. This movie is in equal parts, uplifting, depressing, sad and funny and its brilliant. WHM naked in a sex scene? Its worth the price of admission just for that. If that doesn't float your boat then perhaps the gorgeous Maria Bello will.
- DirectorGeorge Roy HillStarsPaul NewmanRobert RedfordKatharine RossIn 1890s Wyoming, Butch Cassidy and The Sundance Kid lead a band of outlaws. When a train robbery goes wrong, they find themselves on the run with a posse hard on their heels. After considering their options, they escape to South America.My favorite western of all time and perhaps a lot of people's choice for best buddy-movie. A fantastic script by William Goldman, great characters and lots of funny lines and scenes. Robert Redford, Paul Newman and Katherine Ross again, it doesn't get much better than that. Best line of the movie when Sundance tells Butch he can't swim and Butch retorts "Don't worry the fall will probably kill you anyway."
- DirectorElaine MayStarsWalter MatthauElaine MayJack WestonHenry Graham lives the life of a playboy. When his lawyer tells him one day that his lifestyle has consumed all his funds, he needs an idea to avoid climbing down the social ladder. So he intends to marry a rich woman and - murder her.Here's one from left-field for you. Most people have never even heard of this but its a classic. Walter Matthau at his curmudgeonly best. After having squandered his inheritance he plots to marry and murder a rich spinster. Beautifully written and directed by the leading lady Elaine May this is an always funny and ultimately moving film. Honorable mention also goes to George Rose as the perfectly understated Gentleman's gentleman.
- DirectorSpike JonzeStarsJohn CusackCameron DiazCatherine KeenerA puppeteer discovers a portal that leads literally into the head of movie star John Malkovich.Super quirky, super funny. A totally offbeat film about a portal into the head of actor John Malkovitch who plays himself. Another masterpiece from the pen of Charlie Kaufman.
- DirectorJez ButterworthStarsNicole KidmanVincent CasselBen ChaplinA thirtysomething bank clerk from St Albans has his small-town life exploded by the arrival of his Russian mail-order bride.A clever, funny British import. Ben Chaplin as a dorky English assistant bank manager and Nicole Kidman as a crooked Russian mail-order bride are superb. Great supporting work by Vincent Cassel and Mathieu Kassovitz has this movie humming along. Kidman plays a mean Russian. And by mean I mean good if you know what I mean.
- DirectorCharlie KaufmanStarsPhilip Seymour HoffmanSamantha MortonMichelle WilliamsA theatre director struggles with his work, and the women in his life, as he creates a life-size replica of New York City inside a warehouse as part of his new play.A play within a play within a movie. Probably not everyone's cup of tea but obviously I love it. Its got Philip Seymore Hoffman in it for one thing who never puts a foot wrong in this or anything else he has done. It was written by Charlie Kaufman who is simply a comedy/drama genius ('scuse my grammar.) I had to watch this movie three times to follow the machinations of all the character's storylines but each viewing was a labor of love. Everything about this move is absurd but the absurdity sneaks up on you - genius.
- DirectorBobby FarrellyPeter FarrellyStarsWoody HarrelsonRandy QuaidBill MurrayA star bowler whose career was prematurely "cut off" hopes to ride a new prodigy to success and riches.Perhaps this is more comedy than drama but it has a serious message about redemption and forgiveness and blah, blah, blah. More importantly it has Woody Harrelson, Bill Murray and Randy Quaid and it was directed by the Farrelly Brothers who I had to include somewhere in this list. And last but not least it has the mesmorisingly beautiful Vanessa Angel in it (Why have I not seen more of her?)
- DirectorQuentin TarantinoStarsJohn TravoltaUma ThurmanSamuel L. JacksonThe lives of two mob hitmen, a boxer, a gangster and his wife, and a pair of diner bandits intertwine in four tales of violence and redemption.Maybe not everyone's idea of comedy but it has some extremely wry comic moments. A "black" comedy then, and I mean that in the old-fashioned sense: a comedy with dark overtones. Whichever way you want to look at it, its brilliant. John Travolta's come-back movie, a change of direction for Bruce Willis and a triumph for Tarantino.
- DirectorFrank OzStarsSteve MartinMichael CaineGlenne HeadlyTwo con men try to settle their rivalry by betting on who can swindle a young American heiress out of fifty thousand dollars first.I know its a real stretch to call this drama but its achingly funny and I wanted to get Steve Martin onto this list somehow and that I've got Michael Caine to boot.. well come on. It does have a great story too. Two master con artists trying to help out a poor damsel in distress. (The scene where Martin's wheelchair bound Freddy character is being "tested" by Caine's Lawrence is one of the funniest scenes ever put on celluloid.) In case you are the last person on the planet not to have seen this picture I won't spoil the ending for you here. Just go and watch it now!
- DirectorCharles CrichtonJohn CleeseStarsJohn CleeseJamie Lee CurtisKevin KlineIn London, four very different people team up on a jewel heist, then try to double-cross one another for the loot, complicated by their efforts to fool a very proper barrister.Brilliant movie. Very, very funny. Amazing cast. Hope no one from PETA saw it.
- DirectorMichel GondryStarsJim CarreyKate WinsletTom WilkinsonWhen their relationship turns sour, a couple undergoes a medical procedure to have each other erased from their memories forever.OK so I obviously have a "thing" for Charlie Kaufman who wrote this brilliant comedy starring Jim Carrey (yes I know what I said earlier but this is an exception) and Kate Winslet. The plot has a wonderful twist at the end and the writing is as always sublime. Great direction too - the consistent dream like quality of the camera work and lighting fit the plot to a T. Movie magic.
- DirectorSpike JonzeStarsNicolas CageMeryl StreepChris CooperA lovelorn screenwriter becomes desperate as he tries and fails to adapt 'The Orchid Thief' by Susan Orlean for the screen.Yeah, yeah I know, yet another Kaufman creation but this is another great movie. How great is it? Even Nicholas Cage couldn't ruin it, despite playing two different characters! Twins admittedly, but still! It also has Meryl Streep in it so you know the script must have been Grade A material at the very least. The fact is that its also superbly well acted and directed. So there.
- DirectorLewis GilbertStarsMichael CaineJulie WaltersMichael WilliamsAn alcoholic professor has been hired by a working-class girl for higher education.A lovely story and lots of laughs. Michael Caine plays a great alcoholic, his costar Julia Walters is a well known TV actress and commedienne in her UK homeland. A really charming film.
- DirectorJoel CoenEthan CoenStarsWilliam H. MacyFrances McDormandSteve BuscemiMinnesota car salesman Jerry Lundegaard's inept crime falls apart due to his and his henchmen's bungling and the persistent police work of the quite pregnant Marge Gunderson.This is an easy one. Probably on everyone's list. Chalk up another comedic masterpiece to the Cohen Bros. Quirky, clever, unpredicable: all the CB hallmarks and how freaking good is William H. Macy? A must see movie.
- DirectorJohn BadhamStarsRichard DreyfussEmilio EstevezMadeleine StoweTwo detectives observe an escaped convict's ex-girlfriend, but complications set in when one of them falls for her.I know I really enjoyed this movie but I can't remember too much about it other than that it was funny and thrilling.
- DirectorHerbert RossStarsRichard DreyfussMarsha MasonQuinn CummingsAfter being dumped by her live-in boyfriend, an unemployed dancer and her 10-year-old daughter are reluctantly forced to live with a struggling off-Broadway actor.A great romantic comedy from the pen of Neil Simon. A youngish Richard Dreyfus stars.
- DirectorChris BernardStarsPeter FirthAlfred MolinaTracy Marshak-NashTwo Soviet sailors, Peter and Sergei, go ashore in Liverpool to spend one night on the town. Peter can speak a minimal amount of English but it's enough to make contact with two Liverpudlian natives, Elaine and Theresa. Elaine and Peter immediately fall in love with each other, but the night is short and they must leave with the ship. Elaine can't forget him and writes a letter to Soviet General Secretary Leonid Brezhnev, asking him to make it possible for them to reunite.Its unlikely you've seen this but its definitely worth a look if you are into quirky low budget English comedy. Its the story of two factory girls from Liverpool who hook up with a couple of Russian sailors at the height of the cold war.
- DirectorMichael RitchieStarsJames WoodsLouis Gossett Jr.Bruce DernGabriel's released from prison. His con man friend makes a foolish bet with Diggstown's owner on who'd win the boxing matches - their man against ten Diggstown men.Saw this so long ago... but I do remember laughing a lot and being very entertained. I should probably watch it again since I am recommending it huh?