The 14 Best Comedy Movies of All Time—From The Naked Gun to Modern Classics

Image Credit: Wikimedia Commons

The 14 Best Comedy Movies of All Time—From The Naked Gun to Modern Classics

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Christian Wiedeck, M.Sc.

1. The Naked Gun (1988)

1. The Naked Gun (1988) (image credits: wikimedia)
1. The Naked Gun (1988) (image credits: wikimedia)

Leslie Nielsen’s deadpan delivery made *The Naked Gun* an instant classic. The film is packed with ridiculous sight gags, puns, and over-the-top slapstick. Who can forget the iconic scene where Frank Drebin stumbles through a baseball game, causing chaos? The humor is relentless, never giving the audience a break from laughter. It’s a perfect example of how absurdity can be genius when done right. Even decades later, the jokes still land perfectly. If you haven’t seen it, you’re missing out on one of the funniest films ever made.

2. Airplane! (1980)

2. Airplane! (1980) (image credits: wikimedia)
2. Airplane! (1980) (image credits: wikimedia)

*Airplane!* redefined what a comedy movie could be with its rapid-fire jokes and surreal humor. The film parodies disaster movies with such precision that it’s impossible not to laugh. Lines like “Surely you can’t be serious” and “I am serious… and don’t call me Shirley” have become legendary. The visual gags, like the autopilot blow-up doll, are just as hilarious as the dialogue. It’s a masterclass in spoof comedy that hasn’t aged a day. Every time you watch it, you catch something new you missed before.

3. Monty Python and the Holy Grail (1975)

3. Monty Python and the Holy Grail (1975) (image credits: wikimedia)
3. Monty Python and the Holy Grail (1975) (image credits: wikimedia)

This medieval farce from the Monty Python team is pure comedic gold. From the Black Knight who refuses to surrender to the killer rabbit, every scene is unforgettable. The film’s low-budget charm only adds to its hilarity, making the absurdity even funnier. The coconut horse sound effects and the nonsensical dialogue are still quoted today. It’s a movie that rewards repeat viewings because the jokes never get old. Few films have managed to be this clever and this silly at the same time.

4. Groundhog Day (1993)

4. Groundhog Day (1993) (image credits: wikimedia)
4. Groundhog Day (1993) (image credits: wikimedia)

Bill Murray’s performance in *Groundhog Day* is nothing short of brilliant. The premise—a man stuck reliving the same day—is simple but executed perfectly. Watching Phil Connors slowly lose his mind while trying to escape the time loop is both funny and oddly relatable. The humor ranges from dry sarcasm to outright ridiculous situations. It’s one of those rare comedies that also makes you think about life. Even after all these years, it remains a must-watch.

5. Superbad (2007)

5. Superbad (2007) (image credits: wikimedia)
5. Superbad (2007) (image credits: wikimedia)

*Superbad* captured the awkwardness of teenage life in the most hilarious way possible. Jonah Hill and Michael Cera’s chemistry is unmatched, delivering cringe-worthy yet heartwarming moments. McLovin’s fake ID escapade is comedy gold, and the cops’ antics make it even funnier. The script is packed with quotable lines that still pop up in conversations today. It’s a coming-of-age story that never tries too hard to be profound—just real and ridiculously funny.

6. Borat (2006)

6. Borat (2006) (image credits: wikimedia)
6. Borat (2006) (image credits: wikimedia)

Sacha Baron Cohen’s *Borat* pushed boundaries in ways few comedies dared. The mockumentary style and unscripted reactions from real people made the humor feel raw and unpredictable. Whether he’s wrestling naked or singing an offensive national anthem, Borat’s antics are unforgettable. The film walks a fine line between shocking and hilarious, and it works perfectly. It’s a bold, no-holds-barred comedy that still shocks new viewers today.

7. The Big Lebowski (1998)

7. The Big Lebowski (1998) (image credits: wikimedia)
7. The Big Lebowski (1998) (image credits: wikimedia)

“The Dude” became an instant icon thanks to Jeff Bridges’ laid-back performance. The Coen Brothers’ stoner noir is weird, wonderful, and endlessly quotable. From the rug that “really tied the room together” to John Goodman’s explosive outbursts, every scene is memorable. The plot meanders in the best possible way, making each rewatch feel fresh. It’s a cult classic for a reason—people just can’t get enough of its oddball charm.

8. Bridesmaids (2011)

8. Bridesmaids (2011) (image credits: wikimedia)
8. Bridesmaids (2011) (image credits: wikimedia)

*Bridesmaids* proved that female-led comedies could be just as raunchy and hilarious as male-driven ones. Kristen Wiig’s meltdown on the plane is comedy perfection, and Melissa McCarthy steals every scene she’s in. The film balances gross-out humor with genuine emotional moments, making it more than just a silly romp. It’s one of the few modern comedies that feels both fresh and timeless.

9. Office Space (1999)

9. Office Space (1999) (image credits: wikimedia)
9. Office Space (1999) (image credits: wikimedia)

Anyone who’s ever worked a boring job will relate to *Office Space*. The satire of corporate culture is as sharp today as it was in the ‘90s. The scene where they destroy the printer is cathartic for anyone who’s ever hated office equipment. It’s a slow-burn comedy that gets funnier with every watch. Few movies capture workplace frustration with this much humor.

10. Anchorman: The Legend of Ron Burgundy (2004)

10. Anchorman: The Legend of Ron Burgundy (2004) (image credits: wikimedia)
10. Anchorman: The Legend of Ron Burgundy (2004) (image credits: wikimedia)

Will Ferrell at his absolute best—*Anchorman* is pure chaos in the best way. The news team’s ridiculous antics, from the jazz flute to the street fight, are iconic. The improvisational style makes every line delivery unpredictable and hilarious. It’s the kind of movie where you miss half the jokes because you’re still laughing at the last one.

11. Shaun of the Dead (2004)

11. Shaun of the Dead (2004) (image credits: wikimedia)
11. Shaun of the Dead (2004) (image credits: wikimedia)

Edgar Wright’s zombie comedy is both smart and ridiculously funny. The clever writing makes even the dumbest moments feel brilliant. Simon Pegg and Nick Frost’s chemistry elevates every scene, especially their clueless zombie survival plan. It’s a perfect blend of horror and humor that never takes itself too seriously.

12. This Is Spinal Tap (1984)

12. This Is Spinal Tap (1984) (image credits: wikimedia)
12. This Is Spinal Tap (1984) (image credits: wikimedia)

The granddaddy of mockumentaries, *This Is Spinal Tap* is still the gold standard. The satire of rockstar egos and cluelessness is spot-on. Quotes like “These go to eleven” have entered pop culture permanently. It’s so well-made that some people still think it’s a real documentary.

13. The Hangover (2009)

13. The Hangover (2009) (image credits: wikimedia)
13. The Hangover (2009) (image credits: wikimedia)

The mystery of what happened in Vegas drove this comedy to instant fame. Zach Galifianakis’s weirdo character is the heart of the chaos. The tiger, the baby, and Mike Tyson’s cameo are just the beginning. It’s a wild ride that never lets up from start to finish.

14. Step Brothers (2008)

14. Step Brothers (2008) (image credits: wikimedia)
14. Step Brothers (2008) (image credits: wikimedia)

Will Ferrell and John C. Reilly as grown men acting like children is comedy gold. The bunk bed scene alone is worth the watch. It’s stupid humor done right—completely unapologetic and endlessly quotable. Few movies make immaturity this entertaining.

These films prove that great comedy is timeless. Whether you’re in the mood for slapstick, satire, or sheer absurdity, there’s something here for every sense of humor. Which one will you watch tonight?

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