39 Good Smart Comedy Movies to Watch

One of the most creative comedies ever made.

This might just be the most insightful movie about men. Watch if you are a guy and you will cringe endlessly from seeing yourself in the characters, and if you are a girl  you should also watch it to laugh and understand the men around you better (yes, it is that insightful). Rob Gordon, a music fanatic who owns a record store, tells the stories of how his relationships ended, included the one ongoing. So if you are asking if this is a romantic comedy about a man trying to move on from a breakup, yes, it is. And it Works. High Fidelity is in fact funny, interesting and comes with a unique look at relationships. But it is mostly simple and entertaining, and with perfect performances from John Cusack and Jack Black as well as an immaculate soundtrack, it is a must-watch.

In this comedy/drama, Bill Murray plays an aged, dispirited war veteran named Vincent who openly disdains most people and gives little attention to anything beyond alcohol and horse racing. Living a life of solitude in Brooklyn, everything takes a turn when a young single mother (Melissa McCarthy) and her son Oliver move in next door. Vincent eventually takes on the responsibility of watching over Oliver when Maggie is at work. Murray is perfectly unpleasant in his darkly comedic role, as his relationship with Oliver evolves despite his own misgivings, providing young Oliver (Jaeden Lieberher) with the fatherly/grandfatherly presence he desperately needs. Though somewhat formulaic, St. Vincent rises above expectations by way of great dialogue, favourable performances from all of the leads, and an unbelievably touching finale that will melt your heart. Much better than you probably expect—definitely check this one out.

An American romantic comedy, Beginners is told through a series of flashbacks telling the story of Oliver and his complicated and difficult relationship with his father. The film is gorgeously heartbreaking, demonstrating how hurtful we are to those we love, while showing the ties of mutual need that bind people. In the way it also takes on the process of finding one's happiness, through the character's eyes and his father's, what that process has in common for both, and how one is inspired from the other. Beginners is lovely, funny, interesting, and above all very enjoyable.

A heartwarming and (ironically) heartbreaking indie film based around the lives of Mary, an 8-year old girl from Australia, and her pen pal Max, a 44-year old man from America. The film follows these two as they deal with life's complications, from the perspective of a child and an autistic man. One of the most riveting and diverse films I've seen, with many joyous moments and cold plot twists. Would recommend 8 condensed milks out of 10.

Shot in black and white to be the best dialogue-driven, character-study film it can be; Blue Jay stars Sarah Paulson and Mark Duplass in a cozy, slow-burning film. Their characters, respectively Amanda and Jim, are former high-school sweethearts who run into each other in their hometown 20 years later. They talk, they get coffee, and then beer and jelly beans, until they find themselves to Jim’s mother’s house. As they familiarize themselves again, and the movie moves forward, it abandons its romantic chops to become a truly heartfelt and real film. A revelation of a movie.

Enough Said is a realistically sweet movie that handles serious emotions without compromising its comedic chops. It portrays the difficulties and doubts that come with post-divorce relations in a somewhat goofy and original way. James Gandolfini is impeccably wonderful in his last lead role, and joined by Julia Louis-Dreyfus they generate exquisite chemistry right from their first scene together all the way until the movie ends. Like many other beautiful movies such as Your Sister’s Sister, Enough Said is hilarious, romantic, but to that it adds being smart and realistic. You'll love it.

It's often said that trying to make a comedy movie featuring a character with cancer is just a bad idea. And while there may be a good share of failed attempts in that category, 50/50 is not one of them. In a movie that comes closer to a believable real life situation than most, 50/50 manages to mine humor, pathos and simple honesty from a dark and traditional situation.  Starring Seth Rogan and Joseph Gordon-Levitt, this film isn't afraid to 'go there' but you'll enjoy the journey.

Sit back, relax, and wait for the feels. With amazing performances from the ensemble cast including Julianne Moore, Mark Ruffalo and Annette Bening, as well as excellent directing; The Kids Are Alright is a highly realistic yet entertaining take on family, growing up, and witnessing children grow up. Two kids meet the sperm donor who enabled their parents to have them, and develop a relationship with him. This confuses everyone as to how it redefines their status, from the parents who add a major issue to their already delicate relationship, to the laid-back and lovingly goofy sperm donor (portrayed perfectly by Ruffalo). The Kids Are Alright is beautifully emotional, funny, and just overall a pleasant watch. Nominated to four Oscars and winner of two Golden Globes.

Four Lions is as black and as dark as a movie can ever get, mixing cultural relevancy with humor and ridiculousness. It is insensitive to Islam, insensitive to terrorism and insensitive to the viewer. But it is hilarious. The director spent three years talking to Imams, terrorism experts and basically everyone. The result? A legit 97 minutes that will dazzle even extremists with its knowledge of Islam and the accuracy of its lines. Needless to say that it will upset quite a few people, but that is always a good sign for black comedy movies, right?

The Fundamentals of Caring is an offbeat comedy/drama starring Paul Rudd as a man attempting to overcome his looming divorce by becoming the caretaker for a teenager with muscular dystrophy (Craig Roberts, Submarine). The two develop an unconventional relationship based largely on sarcasm and profanity, delivering many laugh-out-loud moments, while also slowly exposing the pain each is carrying inside.Together, at Ben’s urging, they embark on a road trip across the western United States for Craig to see the world. It’s somewhat formulaic but fun and touching road movie that covers much familiar ground, but also offers a fine illustration of caregiving, personal growth, and emotional healing. Paul Rudd is as good ever, and Roberts is utterly superb. One of the best movies on the Netflix Originals catalog, and an undeniable winner, all-in-all.