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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When Harry Met Sally... (1989)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship. (96 mins.)
Director: Rob Reiner
“ 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. ” - steveoinsd
Groundhog Day (1993)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A weatherman finds himself living the same day over and over again. (101 mins.)
Director: Harold Ramis
“ 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." ” - steveoinsd
Sideways (2004)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
Two 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. (126 mins.)
Director: Alexander Payne
“ 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. ” - steveoinsd
Swingers (1996)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Wannabe actors become regulars in the stylish neo-lounge scene; Trent teaches his friend Mike the unwritten rules of the scene. (96 mins.)
Director: Doug Liman
“ 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..." ” - steveoinsd
The Graduate (1967)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
A disillusioned college graduate finds himself torn between his older lover and her daughter. (106 mins.)
Director: Mike Nichols
“ 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. ” - steveoinsd
The Cooler (2003)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
In an old school Las Vegas casino, its top gambling jinx breaks his curse when he falls in love, much to his boss' consternation. (101 mins.)
Director: Wayne Kramer
“ 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. ” - steveoinsd
Butch Cassidy and the Sundance Kid (1969)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
Two Western bank/train robbers flee to Bolivia when the law gets too close. (110 mins.)
Director: George Roy Hill
“ 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." ” - steveoinsd
A New Leaf (1971)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Henry 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. (102 mins.)
Director: Elaine May
“ 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. ” - steveoinsd
Being John Malkovich (1999)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A puppeteer discovers a portal that leads literally into the head of movie star John Malkovich. (112 mins.)
Director: Spike Jonze
“ 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. ” - steveoinsd
Birthday Girl (2001)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
A thirtysomething bank clerk from St Albans has his small-town life exploded by the arrival of his Russian mail-order bride. (93 mins.)
Director: Jez Butterworth
“ 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. ” - steveoinsd
Synecdoche, New York (2008)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
A 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. (124 mins.)
Director: Charlie Kaufman
“ 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. ” - steveoinsd
Kingpin (1996)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A star bowler whose career was prematurely "cut off" hopes to ride a new prodigy to success and riches. (113 mins.)
“ 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?) ” - steveoinsd
Pulp Fiction (1994)
    1 2 3 4 5 6 7 8 9 10 8.9/10 X  
The lives of two mob hit men, a boxer, a gangster's wife, and a pair of diner bandits intertwine in four tales of violence and redemption. (154 mins.)
“ 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. ” - steveoinsd
Dirty Rotten Scoundrels (1988)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Two con men try to settle their rivalry by betting on who can swindle a young American heiress out of $50,000 first. (110 mins.)
Director: Frank Oz
“ 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! ” - steveoinsd
A Fish Called Wanda (1988)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
In London, four very different people team up to commit armed robbery, then try to doublecross each other for the loot. (108 mins.)
“ Brilliant movie. Very, very funny. Amazing cast. Hope no one from PETA saw it. ” - steveoinsd
Eternal Sunshine of the Spotless Mind (2004)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
When their relationship turns sour, a couple undergoes a procedure to have each other erased from their memories. But it is only through the process of loss that they discover what they had to begin with. (108 mins.)
Director: Michel Gondry
“ 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. ” - steveoinsd
Adaptation. (2002)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A lovelorn screenwriter becomes desperate as he tries and fails to adapt 'The Orchid Thief' by Susan Orlean for the screen. (114 mins.)
Director: Spike Jonze
“ 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. ” - steveoinsd
Educating Rita (1983)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
In London, the twenty-seven year-old hairdresser Rita decides to complete her basic education before having children as desired by her husband Denny... (110 mins.)
Director: Lewis Gilbert
“ 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. ” - steveoinsd
Fargo (1996)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
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. (98 mins.)
Director: Joel Coen
“ 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. ” - steveoinsd
Stakeout (1987)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
Two cops have to observe a woman. One of them falls in love with her. (117 mins.)
Director: John Badham
“ I know I really enjoyed this movie but I can't remember too much about it other than that it was funny and thrilling. ” - steveoinsd
The Goodbye Girl (1977)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
After 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. (111 mins.)
Director: Herbert Ross
“ A great romantic comedy from the pen of Neil Simon. A youngish Richard Dreyfus stars. ” - steveoinsd
Letter to Brezhnev (1985)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
Two Soviet sailors, Peter and Sergei, go ashore in Liverpool to spend one night on the town. Peter can... (94 mins.)
Director: Chris Bernard
“ 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. ” - steveoinsd
Diggstown (1992)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Gabriel Caine has just been released from prison when he sets up a bet with a business man. The business... (98 mins.)
Director: Michael Ritchie
“ 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? ” - steveoinsd