25
Films Ranked
$4B+
Combined Box Office
10+
Oscars Won
1959-2011
Years Spanning
Airplane!(1980)
Directed by Jim Abrahams, David Zucker, Jerry Zucker — Robert Hays, Julie Hagerty, Leslie Nielsen
$171M worldwide
Airplane! has the highest joke-per-minute ratio of any film in history. It invented the modern spoof genre, launched Leslie Nielsen's comedy career, and killed the disaster movie genre with a single blow. Forty-five years later, 'Don't call me Shirley' still gets a laugh. It is comedy's Everest.
Caddyshack(1980)
Directed by Harold Ramis — Chevy Chase, Bill Murray, Rodney Dangerfield
$39.8M worldwide
Caddyshack put Murray, Chase, and Dangerfield together and let them improvise. The result is the most quotable comedy of the 1980s. Carl Spackler's gopher hunt is the funniest subplot in film history. It defined the comedy of a generation and remains the gold standard for ensemble improvisation.
The Big Lebowski(1998)
Directed by Joel Coen, Ethan Coen — Jeff Bridges, John Goodman, Steve Buscemi
$46.2M worldwide
The Big Lebowski created a cultural movement. Jeff Bridges' Dude is one of the most iconic characters in comedy history. The Coen Brothers proved that a film could fail commercially and still become the most beloved comedy of its era. It spawned a religion. That's, like, the ultimate achievement, man.
Monty Python and the Holy Grail(1975)
Directed by Terry Gilliam, Terry Jones — Graham Chapman, John Cleese, Eric Idle
$5M worldwide
Holy Grail proved that comedy does not need money — it needs wit. Every scene is quotable. The coconut horses, born from a budget constraint, became the film's most iconic joke. It spawned Spamalot, endless memes, and a comedy lexicon that is still in daily use fifty years later.
Groundhog Day(1993)
Directed by Harold Ramis — Bill Murray, Andie MacDowell, Chris Elliott
$105M worldwide
Groundhog Day is the rare comedy that philosophers, monks, and theologians study alongside comedy fans. Bill Murray's performance spans the entire human emotional spectrum. The time-loop concept became a genre unto itself. It proves that the funniest comedies can also be the most profound.
Superbad(2007)
Directed by Greg Mottola — Jonah Hill, Michael Cera, Christopher Mintz-Plasse
$170M worldwide
Superbad is the defining high school comedy of its generation. McLovin became an instant cultural icon. Beneath the R-rated humor is a genuine, moving story about friendship and the fear of growing apart. Rogen and Goldberg wrote it at 13 and perfected it at 25 — that combination of teenage honesty and adult craft is unbeatable.
Bridesmaids(2011)
Directed by Paul Feig — Kristen Wiig, Maya Rudolph, Melissa McCarthy
$288M worldwide
Bridesmaids shattered the myth that female-led comedies could not compete commercially. Melissa McCarthy became a star overnight. The film combined raunchy humor with genuine emotional depth in ways that male-led comedies rarely attempt. It grossed $288M and changed Hollywood's approach to comedy permanently.
Step Brothers(2008)
Directed by Adam McKay — Will Ferrell, John C. Reilly, Mary Steenburgen
$128M worldwide
Step Brothers is the most quotable comedy of the 2000s. Ferrell and Reilly's chemistry is unmatched. 'So much room for activities!' and 'Did we just become best friends?' are permanent entries in the comedy dictionary. The film's commitment to absurdity is so total that it becomes a kind of purity.
Office Space(1999)
Directed by Mike Judge — Ron Livingston, Jennifer Aniston, Gary Cole
$12.8M worldwide
Office Space is the defining comedy about corporate work culture. Bill Lumbergh is the most recognizable boss in comedy. The printer scene is the most cathartic moment in workplace cinema. It bombed theatrically and became a cult phenomenon on home video — proving that the audience it was made for eventually found it.
Anchorman: The Legend of Ron Burgundy(2004)
Directed by Adam McKay — Will Ferrell, Christina Applegate, Steve Carell
$90.6M worldwide
Anchorman gave the world Ron Burgundy, one of the most iconic comedy characters of the century. 'I'm kind of a big deal.' 'Sixty percent of the time, it works every time.' The news team fight. The jazz flute. It produced so many quotes that it fundamentally altered how a generation communicates.
Blazing Saddles(1974)
Directed by Mel Brooks — Cleavon Little, Gene Wilder, Madeline Kahn
$119.5M worldwide
Blazing Saddles is the most fearless comedy ever made. Brooks used humor as a weapon against racism with a precision that remains unmatched. The fourth-wall-breaking finale invented a comedy technique that films still imitate. It proved that the best satire punches up and never apologizes.
This Is Spinal Tap(1984)
Directed by Rob Reiner — Christopher Guest, Michael McKean, Harry Shearer
$4.7M worldwide
This Is Spinal Tap invented the mockumentary and created the template for The Office, Best in Show, and every pseudo-documentary comedy that followed. 'These go to eleven' is the single most famous joke about rock and roll. Real musicians cannot tell where the parody ends and reality begins.
Dr. Strangelove(1964)
Directed by Stanley Kubrick — Peter Sellers, George C. Scott, Sterling Hayden
$9.4M worldwide
Dr. Strangelove is the greatest political satire in cinema history. Peter Sellers' triple performance is legendary. The bomb-riding finale is the most iconic image of Cold War cinema. Kubrick proved that comedy can be a more powerful weapon against insanity than drama. The film's thesis — that the people in charge of nuclear weapons are as flawed and foolish as the rest of us — has never stopped being relevant.
Some Like It Hot(1959)
Directed by Billy Wilder — Marilyn Monroe, Tony Curtis, Jack Lemmon
$40M worldwide
Some Like It Hot features the greatest closing line in comedy history: 'Nobody's perfect.' Wilder crafted the most structurally perfect farce ever filmed. Monroe, Curtis, and Lemmon are the greatest comedy trio of the studio era. Sixty-five years later, the film's take on gender fluidity feels more modern than most contemporary comedies.
The Hangover(2009)
Directed by Todd Phillips — Bradley Cooper, Zach Galifianakis, Ed Helms
$467M worldwide
The Hangover is the highest-grossing R-rated comedy ever. Galifianakis became an overnight star. The mystery-comedy structure revitalized the genre. The end-credits photos became the most talked-about sequence of 2009. It proved that R-rated comedy could compete with blockbusters at the global box office.
Coming to America(1988)
Directed by John Landis — Eddie Murphy, Arsenio Hall, James Earl Jones
$288M worldwide
Coming to America is Eddie Murphy's masterpiece — the film that showcased his full range as both a leading man and a character actor. The barbershop scenes are the funniest recurring bit of the 1980s. Rick Baker's makeup work was revolutionary. The film grossed $288M and proved that Black-led romantic comedies could dominate the global box office.
Ferris Bueller's Day Off(1986)
Directed by John Hughes — Matthew Broderick, Alan Ruck, Mia Sara
$70.1M worldwide
Ferris Bueller is John Hughes' masterpiece and the defining film about teenage freedom. 'Life moves pretty fast' is the most quoted line in teen cinema. The parade scene is pure joy. Cameron's arc is genuinely moving. It taught a generation that the best days are the ones you seize.
Young Frankenstein(1974)
Directed by Mel Brooks — Gene Wilder, Peter Boyle, Marty Feldman
$86.3M worldwide
Young Frankenstein is the greatest parody film ever made. Gene Wilder's performance is the peak of his career. The 'Puttin' on the Ritz' sequence is the funniest musical number in cinema. Brooks and Wilder proved that parody born from love and knowledge is infinitely funnier than parody born from contempt.
Dumb and Dumber(1994)
Directed by Peter Farrelly, Bobby Farrelly — Jim Carrey, Jeff Daniels, Lauren Holly
$247M worldwide
Dumb and Dumber is the greatest buddy comedy of the 1990s. Jim Carrey's physical comedy is unmatched. Jeff Daniels proved that great dramatic actors can be great comic actors. The film grossed $247M on a $17M budget and proved that pure silliness, performed with total conviction, is a legitimate art form.
Borat(2006)
Directed by Larry Charles — Sacha Baron Cohen, Ken Davitian, Luenell
$262M worldwide
Borat redefined what comedy could be — part character study, part social experiment, part guerrilla journalism. Cohen's commitment to the bit is unmatched in comedy history. The film exposed uncomfortable truths about American prejudice while being relentlessly, painfully funny. It grossed $262M and made the entire world learn the name Kazakhstan.
Beverly Hills Cop(1984)
Directed by Martin Brest — Eddie Murphy, Judge Reinhold, John Ashton
$316M worldwide
Beverly Hills Cop made Eddie Murphy the biggest star in the world and invented the action-comedy as a mainstream genre. The 'Axel F' theme is iconic. Murphy's improvisational genius turned every scene into a masterclass. It was the highest-grossing film of 1984 and launched one of the decade's most profitable franchises.
Mean Girls(2004)
Directed by Mark Waters — Lindsay Lohan, Rachel McAdams, Tina Fey
$129M worldwide
Mean Girls is the most quotable teen comedy of the 21st century. Tina Fey's script turned high school anthropology into art. Rachel McAdams' Regina George is the greatest teen villain since Heathers. October 3rd is now an unofficial holiday. The film proved that smart, female-driven comedy could define a generation.
Trading Places(1983)
Directed by John Landis — Eddie Murphy, Dan Aykroyd, Jamie Lee Curtis
$90.4M worldwide
Trading Places is the smartest social satire disguised as a buddy comedy. Murphy and Aykroyd are a perfect odd couple. The commodities-trading climax turns finance into cinema. The film's thesis — that privilege is arbitrary — was ahead of its time and has only become more relevant.
The 40-Year-Old Virgin(2005)
Directed by Judd Apatow — Steve Carell, Catherine Keener, Paul Rudd
$177M worldwide
The 40-Year-Old Virgin launched Judd Apatow's career and redefined R-rated comedy for a generation. Steve Carell became a leading man. The chest-waxing scene is the most talked-about comedy scene of the 2000s. The film proved that raunchy comedy and genuine heart are not mutually exclusive.
Shaun of the Dead(2004)
Directed by Edgar Wright — Simon Pegg, Nick Frost, Kate Ashfield
$30M worldwide
Shaun of the Dead perfected the genre comedy by being equally excellent as a horror film, a rom-com, and a buddy movie. Edgar Wright's visual comedy is unmatched. The Queen fight scene is the funniest genre sequence of the century. It launched the Cornetto Trilogy and proved that British comedy could conquer the global market.
Frequently Asked Questions
What is the funniest movie of all time?
Airplane! (1980) is widely considered the funniest movie ever made. The Zucker brothers and Jim Abrahams achieved the highest joke-per-minute ratio in film history — roughly three gags per minute for 88 straight minutes. Leslie Nielsen's deadpan delivery ('I am serious, and don't call me Shirley') reinvented comedy and launched an entirely new genre of spoof films.
What makes a comedy 'great' versus just 'funny'?
The greatest comedies are not just funny — they are rewatchable, quotable, and culturally influential. Films like The Big Lebowski and Office Space were box office disappointments that became cultural institutions. Groundhog Day is studied by philosophers and theologians. The best comedies reveal something true about the human condition while making you laugh.
Why are so many comedies from the 1970s and 1980s ranked highly?
The 1970s and 1980s were a golden age for comedy filmmaking. Mel Brooks, the Monty Python troupe, the Zucker brothers, John Hughes, and early Eddie Murphy and Bill Murray were all working at their creative peaks. Comedy was less restricted by franchise obligations and more willing to take creative risks. Many of these films could not be made today, which paradoxically increases their cultural value.
Are there any recent comedies on the list?
Superbad (2007), Bridesmaids (2011), Step Brothers (2008), The Hangover (2009), Borat (2006), and Shaun of the Dead (2004) all represent 21st-century comedy at its best. The Judd Apatow era proved that R-rated comedy could combine raunchy humor with genuine emotional depth, while Edgar Wright and Sacha Baron Cohen pushed the boundaries of what comedy could structurally achieve.
What is the most quotable comedy of all time?
The Big Lebowski, Anchorman, and Monty Python and the Holy Grail are the three most quotable comedies ever made. The Dude's 'That's just, like, your opinion, man,' Ron Burgundy's 'I'm kind of a big deal,' and the Black Knight's 'Tis but a scratch' have all entered everyday language. Step Brothers and Mean Girls are close runners-up.
Get Glen's Musings
Occasional thoughts on AI, Claude, investing, and building things. Free. No spam.
Unsubscribe anytime. I respect your inbox more than Congress respects property rights.
Keep Exploring
Top 25 Action Movies
The greatest action films ever made, ranked.
Read moreTop 25 Sci-Fi Movies
The greatest science fiction films ever made, ranked.
Read moreTop 25 Sports Movies
Rocky, Hoosiers, Rudy — the greatest sports films ranked.
Read moreTop 25 Movie Villains
The greatest antagonists in cinema history, ranked.
Read moreTop 25 Motivational Speeches
The speeches that changed how people think about success.
Read moreConsulting
Salesforce development and technical consulting.
Read more