27 Best Hollywood Comedy Movies of All Time For Fun Night

Discover the Timeless Allure of Hollywood’s Evergreen Comedy Genre.

Explore Hollywood comedy’s vast and renowned world, a genre cherished by cinema enthusiasts worldwide. Dive into sub-genres like romantic, black, insult, sitcom, musical, surreal, and more, showcasing the genre’s immense popularity.

Hollywood has continually delighted audiences with diverse comedy films since its inception, creating a legacy of funny storytelling, exceptional acting, and memorable dialogues. Through the decades, filmmakers have tirelessly entertained us, leaving an indelible mark with punchlines that have become integral to our daily lives.

These iconic Hollywood comedy films not only serve as a source of laughter but also offer a welcome escape from the stresses of daily life. Join me as we celebrate the Greatest Hollywood Comedy Films of All Time, adding joy and humor to those seeking it.

List of Best Hollywood Comedy Movies

We are sharing the list of Best Hollywood Comedy Movies and the best old classic comedy films and comedy films of the 90s and 2000s decade.

Checkout the list of Best Comedy Films

Duck Soup (1933)

Duck Soup

Duck Soup is a 1933 classic comedy film starring The Marx Brothers. Leo McCarey directs the film and marks as the last film to feature all the four Marx brothers; Groucho, Harpo, Chico, and Zeppo.

Surprisingly, Duck Soup was a box office disappointment, but it wasn’t a flop. The film has been termed as a masterpiece by many critics over time, and Duck Soup is even today considered one of the iconic comedy films of all time in Hollywood history.

The Great Dictator (1940)

The Great Dictator identity crisis theme

Well, the first actor that comes to my mind when someone talks about comedy is definitely Charlie Chaplin. Hence, the list of best Hollywood comedy films would be incomplete without a Charlie Chaplin film.

That’s why the 1940 political satire comedy film The Great Dictator is on our list. The film is Charlie Chaplin’s funny take on fascism, which prevailed highly during those times, primarily led by Adolf Hitler.

In the film, Charlie Chaplin plays a double role: one as a ruthless fascist dictator based on Adolf Hitler and as a persecuted Jewish barber.

Some Like It Hot (1959)

Some Like It Hot 1959 comedy film

If you are a man and a Hollywood black and white classic fan, then I bet you must be crazy over the beautiful actress Marilyn Monroe.

And that brings us to our next film on the list, Some Like It Hot. Some Like It Hot is a 1959 classic romcom set in 1929, directed by Billy Wilder. Starring Marilyn Monroe, Tony Curtis, and Jack Lemmon in the lead roles.

Some Like it Hot is about two musicians who dress in drag to hide from the Mafia gangsters whom they saw commit the Saint Valentine’s Day massacre. The film was first of its kind to feature cross-dressing as well as playing with the concept of homosexuality in films.

Monty Python and the Holy Grail (1975)

Monty Python and the Holy Grail 1975

If you are a fan of comedy as a genre, then you must have heard about the Monty Python group, a British Surreal Comedy group highly active during the 70s.

The group was famous for its sketch comedy series Monty Python’s Flying Circus premiered in 1969. But we are talking about films and it will be unfair not to include one of their best works in Monty Python and the Holy Grail, released in 1975.

Unlike their first film, Monty Python and the Holy Grail focused on a new material instead of relying on a compilation of sketches. The film was based on the legend of King Arthur’s quest to find the Holy Grail.

The popularity of this film and the group can be assessed by the fact that the Monty Python’s influence on comedy is compared to the Beatles on music.

Annie Hall (1977)

Annie Hall 1977 comedy film

Next on our list is a Woody Allen film Annie Hall released in 1977. The film is a fantastic rom-com starring Woody Allen as Alvy “Max” singer and Diane Keaton as his love interest.

Being a romantic comedy, the film follows the life of Max in a comical way while he is trying to figure out the reasons for the failure of his relationship with Annie Hall, played by Diane Keaton.

If you are aware of Woody Allen’s legacy, then you will be amazed to know that the film Annie Hall began his streak of directing at least one film every year and the run is still active as of 2016 as well!

Airplane! (1980)

Airplane 1980 comedy film

Few of the brilliant Comedy films in Hollywood are actually parody films that are based on serious drama or action films. Airplane! is one such satirical parody film written and directed by David and Jerry Zucker and Jim Abrahams.

The film stars one of the best comedy actors of all time, none other than Leslie Nielsen, who is well-known for his antics and his comic timing. The film is basically a parody of 1957 disaster film Zero Hour! and at the same time, the film also borrows some elements from the film Airport 1975.

The film is highly regarded among the best comedy films of all time for its surreal humour and the visual as well as verbal puns and gags.

Ghostbusters (1984)

Ghostbusters 1984 film comedy

If you are the 80s or 90s kids, then you must be aware of the popular supernatural animation show, The Real Ghostbusters, and Extreme Ghostbusters.

Well, these supernatural series were actually produced after the Ghostbusters franchise debuted with the 1984 supernatural comedy film Ghostbusters. Directed by Ivan Reitman, the film starred Bill Murray, Dan Aykroyd, and Harold Ramis as the Ghostbusters, who start a ghost-catching business in New York City.

Aykroyd and Ramis have also written the film’s story together.

Dumb & Dumber (1994)

Dumb & Dumber 1994 film

If you prepare a list of iconic comedians in the Hollywood history, Jim Carrey would surely make it to the top 10 list.

One of his biggest hits and cult favourite film, Dumb & Dumber proves his mantle along with several other films as a comic actor. Directed by Peter and Bobby Farrelly, the film follows the life of Lloyd Christmas, played by Jim Carrey, and Harry Dunne, played by Jeff Daniels. Both Christmas and Dunne are dumb guys as well as best friends and roommates.

The film becomes special with some comic goof-ups and idiotic moments beautifully crafted by the two lead actors justifying the title of the movie in true essence.

Four Weddings And A Funeral (1994)

Four Weddings And A Funeral

Four Weddings And A Funeral is a 1994 British romantic comedy film starring Hugh Grant and Andie MacDowell in the lead roles.

The film’s unusual title assures that it will be something interesting and funny, to begin with.   Well, the film follows the romantic story of Charles and Carrie, who meet each other at four weddings and a funeral, which justifies the film’s unusual title.

The film also marks the first of the several films featuring the collaboration of screenwriter Richard Curtis and Hugh Grant.

The Big Lebowski (1998)

the big lebowski 1998 film

Just imagine what ruckus mistaken identities can cause in real life. Well, why to imagine when you can visualize it in the 1998 crime comedy film The Big Lebowski.

The cult favorite film follows the life of Jeffrey “The Dude” Lebowski, who is mistaken for a millionaire also named Jeffrey Lebowski and is dragged into a mess that it involves all sorts of crimes.

Directed by Joel and Ethan Coen, the film was a box-office disappointment at the time of its release but eventually became a cult favorite as it garnered accolades for its idiosyncratic characters, dream sequences, unconventional dialogues, and eclectic soundtrack.

American Pie (1999)

American Pie

One of the most controversial films at the time of its release as well as one of the best sex comedies of all time, American Pie makes it to our list as well. Directed by Paul and Chris Weltz, the film is the first installment of the American Pie film series.

The film basically follows the life of five best friends, who make a pact, except Stifler, to lose virginity before their high school graduation. From there, a series of funny incidents follow in their conquest to score with girls to complete the pact.

Office Space (1999)

office space 1999 film

Office Space, as the title suggests, is a 1999 comedy-drama based on a typical office life in the IT industry of the 90s. Directed by Mike Judge; the film stars Ron Livingston, Jennifer Aniston, Gary Cole, Stephen Root, David Herman, Ajay Naidu and Diedrich Bader.

Because of the widespread office culture because of the IT revolution during that time, the film Office Space earned a cult status among its fans and is considered to be one of the best films based on white-collar employees and workforce themes. The film is inspired by Mike Judge’s animated series Milton.

Also Read: Best Hollywood Cult Movies of All the Time

Anchorman: The Legend of Ron Burgundy (2004)

Anchorman The Legend of Ron Burgundy

While Office Space was about the office culture of the IT industry in the 90s, Anchorman: The Legend of Ron Burgundy is a 2004 comedy film based on the 70s Action news format.

Basically, the film follows the life of Ron Burgundy, played by Will Ferrell, a famous anchorman for the local San Diego TV station. The film’s main theme is the rivalry between Ron and his new co-anchor Veronica, played by Christina Applegate, and a series of funny and hilarious moments caused by the fierce competition between the two.

The film also stars Paul Rudd, Steve Carell, David Koechner, Chris Parnell, Kathryn Hahn, and many others.

Wedding Crashers (2005)

Wedding Crashers comedy movies

Wedding Crashers is a romantic comedy film starring Owen Wilson and Vince Vaughn, who play the titular characters as the wedding crashers.

The duo in the film plays John Beckwith and Jeremy Grey respective, who are divorce mediators in Washington D.C. They are expert playboys who crash wedding parties to meet and bed a woman.

However, things get complicated when John falls for Clair, the maid of honor, at one of the weddings they crash. The film also stars Christopher Walken, Rachel Adams, Isla Fisher, Bradley Cooper, and many others in important roles.

Kiss Kiss Bang Bang (2005)

Kiss Kiss Bang Bang 2005

Presumably the first black comedy on our list, Kiss Kiss Bang Bang is one of the best black comedies I have ever seen. Starring Robert Downey Jr. and Val Kilmer in the lead roles, the film is adapted from Brett Halliday’s novel Bodies Are Where You Find Them.

Directed by Shane Black, the film is about Harry Lockhart, played by Robert Downey Jr., a petty thief who successfully auditions for a film while escaping police during a chase.

However, things turn ugly when he becomes involved in a murder mystery along with his Perry, played by Val Kilmer, the private investigator hired to help Harry study the role. Although dark, the film will make you laugh at the tragedies that follow in the life of Harry.

The 40-Year-Old Virgin (2005)

The 40-Year Old Virgin

The 40-Year Old Virgin is a 2005 American comedy film that follows the life of a 40-year old man Andy Stitzer, played by Steve Carell, who is a virgin and lives alone, collects action figures, plays video games and works at an electronics store named SmartTech.

When Andy’s co-workers find that he’s still a virgin, they team up to help Andy lose his virginity by making him do stuff that he has never done before while trying to hook him up with every possible woman they come across.

Directed by Judd Apatow, the film is a laughter ride as you see how the group unsuccessfully tries to help Andy lose his virginity. The film also stars Catherine Keener, Paul Rudd, Romany Malco, Seth Rogen, Elizabeth Banks and many others.

Borat (2006)


Borat is one of the funniest films you will ever watch in the mockumentary comedy genre. Larry Charles directs the film and follows the life of the title character Borat Sagdiyev, a fictitious Kazakh journalist visiting the United States to record real-life interactions with Americans.

The film is written by Sacha Boran Cohen, who also plays the lead role of Borat in the film. Borat gets funnier and funnier as the Americans interviewed by Borat believe him to be a foreigner with no knowledge of American customs and results in funny and hilarious outcomes.

Knocked Up (2007)

Knocked Up 2007

Knocked Up is a 2007 American romantic comedy starring Seth Rogen and Katherine Heigl in the lead roles. The film is basically about a one-night stand between Alison Scott, played by Heigl, and Ben Stone, played by Rogen, after a drunken night that results in Alison getting pregnant.

Directed by Judd Apatow, the film is actually a delight as the repercussions of the one-night stand change the lives of both Alison and Ben, resulting in them starting a relationship for the sake of their unborn child.

The film also stars Paul Rudd, Ken Jeong, Harold Ramis, and Leslie Mann in pivotal roles.

Superbad (2007)


Superbad is a 2007 American teen comedy starring Jonah Hill and Michael Cera as best friends Seth and Evan.

Directed by Greg Mottola, the film is written by Seth Rogen and Evan Goldberg when they were just 15, who have their character names based on their real names.

Superbad is among the list of super comedies produced by Judd Apatow, who is also known for his excellent directorial work giving films like The 40-year Old Virgin and Knocked Up that are already on the list.

The Hangover (2009)

The Hangover 2009 comedy film

Undoubtedly one of the best comedy films of the new millennium, The Hangover is directed by Todd Philips. The film follows the experience of four friends who set off on a road trip to Las Vegas to celebrate the upcoming wedding of Doug, one of the friends.

However, things turn ugly as the friends Phil, Stu, and Alan, played by Bradley Cooper, Ed Helmes, and Zack Galifianakis respectively wake up from last night’s hangover to find Doug missing without having any memories of the previous night.

Now, the trio must recount the events of the previous night through clues they find on the way to locate Doug before the wedding. The search for their Doug by the trio turns out to be laughter ride for the audiences enlisting the film on the list of best comedy films of all time in Hollywood.

Zombieland (2009)

Zombieland zombie comedy film

Well, if you have been a fan of supernatural thriller films based on Living Dead or Zombies, then I am cent percent sure that you will like the 2009 horror comedy Zombieland.

The film stars an ensemble cast of Woody Harrelson, Jesse Eisenberg, Emma Stone, and Abigail Breslin as the only survivors after a zombie apocalypse.

Directed by Ruben Fleischer, the film basically follows the life of a geek kid named Columbus, played by Eisenberg, who is surviving the different scenarios resulted from the recent Zombie Apocalypse and meets the other characters Tallahassee, Wichita, and Little Rock resulting in a road trip to find a sanctuary free from zombies.

Despicable Me (2010)

Despicable Me

Despicable Me is an interesting film on our list of best Hollywood comedies of all time. For one, it is the first animated film on the list and secondly, the film actually introduced us to minions.

Directed by Pierre Coffin and Chris Renaud, the story of the film follows the life of a supervillain named Felonious Gru, who adopts three girls from an orphanage to infiltrate his rival Vector’s base to retrieve the shrink ray that Vector stole from Gru.

From then on, a series of hilarious events follow in the life of Gru caused by his minions and the girls throughout the film making it a laughter ride for the audience. Owing to the film’s success, a sequel was released in 2013 and a prequel Minions in 2015.

Crazy, Stupid, Love (2011)

Crazy, Stupid, Love 2011

Crazy, Stupid, Love is a 2011 romantic comedy film directed by Glenn Ficarra and John Requa. The film features an ensemble cast of Steve Carell, Ryan Gosling, Julian Moore, Emma Stone, Marisa Tomei, and Kevin Bacon.

The film is about Carl Weaver played by Carell, who finds out that his wife Emily, played by Moore, has cheated on him with a co-worker. While getting drunk at a bar, Carl meets Jacob, played by Gosling, who offers to teach him how to pick up women.

As Carl becomes an expert at picking up women, a surprising truth about Jacob spoils his relationship with him and now he has to make things right with his family as well as with his life.

Ted (2012)

Ted 2012 film

Ted is an American comedy film starring Mark Wahlberg, Mila Kunis and a teddy bear voiced Seth MacFarlane in the lead roles.

Directed by Seth MacFarlane, the film follows the life of John Bennett, a lonely child who finds his best friend in a teddy bear that comes to life during a Christmas night after John wishes for it.

Despite being best friends, the life of Ted and John takes turmoil when their friendship comes in between John and Lori’s relationship causing a lot of funny and hilarious events. A sequel Ted 2 was released in 2015.

Neighbors (2014)

Neighbors 2014 film

Having good relations with your neighbors can help keep the neighborhood friendly and secure. But, what if when you find that your new neighbors are a college fraternity known for outrageous parties? Well, that’s the story of the next film on our list.

Directed by Nicholas Stroller, Neighbors is a 2014 American comedy-drama that would make you wonder what if your neighbors turn out to be the ones in the film.

Starring Seth Rogen, Zac Efron, Rose Byrne, Dave Franco, and Christopher Mintz-Plasse in important roles, the film features the rift between a happy couple and Delta Psi Beta, their new neighbors well-known for their outrageous parties.

Owing to its success, a sequel to the film Neighbors 2: Sorority Rising was released in 2016 with Rogen, Byrne, Efron, and Franco reprising their roles from the previous film.

Paddington (2014)

Paddington 2014

Paddington is a 2014 family comedy film based on the popular fictional character in children’s literature, Paddington Bear created by Michael Bond.

The film stars Ben Whishaw as the title character’s voice, while Hugh Bonneville, Sally Hawkins, Julie Walters, Nicole Kidman, Jim Broadbent, and Peter Capaldi are live-action characters. Directed by Paul King, the film follows the life of a rare species of a bear named Paddington that is intelligent and speaks English.

Paddington arrives in London to find a home for himself with the help of a human friend of his uncle, however, Paddington is lost and finds shelter in the Brown family. Later, a sadistic museum taxidermist named Millicent Clyde, played by Kidman, goes after Paddington to kill him and stuff him for the museum. Whether Paddington survives or not is what makes the rest of the film.

War Dogs (2016)

war dogs 2016 comedy film

War Dogs is a 2016 crime comedy-drama film adapted from an article by Guy Lawson, who later also wrote a book titled Arms and the Dude describing the story in detail.

Directed by Todd Phillips, the film follows the story of two arms dealers Efraim Diveroli and David Packouz, who the US Government hires to supply weapons for U.S. Troupes in Afghanistan.

Although the film is fictionalized and dramatized, some of its events, such as the duo driving through Iraq, were inspired by the real-life experiences of screenwriter Stephen Chin. The film stars Jonah Hill and Miles Teller as the arms dealers duo along with Ana de Adams and Bradley Cooper in supporting roles.

Your Turn!

Note: Most of these films are also available in Hindi or other Indian languages like Tamil, Telugu, Malayalam, and Bengali on Netflix and Amazon Prime.

These are our favorite Hollywood comedy movies. Share your list in the comment section!

Also Check: Best Feel Good Hollywood Movies on Prime