My Top 5 All-Time Comedy Movie Picks

Some nights, you just want a good laugh, no deep plots, no heavy themes, just pure, ridiculous fun. The best comedies are the ones you can rewatch again and again, the kind that lift your mood and make even the dullest Tuesday night feel better. Whether it’s physical humour, clever dialogue, or over-the-top characters, these films all have one thing in common — they deliver when you need a dose of feel-good escapism. I’ll admit, this one was tough to narrow down. there were at least another four or five films I could’ve included. I might just have to make a Part Two!

If you enjoy classic comedies with a bit more edge, check out my post 5 Essential Old-School Comedies That Couldn’t Be Made Today — it’s packed with nostalgia and films that pushed the limits of what comedy could get away with. If you are wondering whether streaming is going to take over completely and wipe out the old disc media, have a read of my post Is Disc Media Dying – or Just Waiting for Its Comeback? and see if you agree with my assessment.

1. Old School (2003)

Three guys in their 30s — played by Luke Wilson, Vince Vaughn, and Will Ferrell — decide to relive their college glory days by starting a fraternity near their old campus. Naturally, chaos follows. Old School is one of those early-2000s comedies that still hits every note, with unforgettable lines, ridiculous stunts, and Ferrell’s legendary “Frank the Tank” performance stealing every scene.

My 2 Cents: This movie is a brilliant comedy with a great cast. It was also unusual as it featured Metallic - Master of Puppets in its soundtrack, a first for the band to allow.It has all the features of an outrageous comedy and finishes on a high.

2. The Dictator (2012)

Sacha Baron Cohen stars as General Aladeen, the eccentric and ruthless leader of the fictional nation of Wadiya. After being betrayed during a trip to New York, he’s forced to live among the people he once ruled — with predictably chaotic results. It’s outrageous, politically incorrect, and full of the kind of shocking humour only Cohen can pull off.

My 2 Cents: I love this movie and I find Sacha Baron Cohen's humour to be right on point. There are little witty references to real life throughout if you are quick enough to spot them. As with all good comedies, the hero goes through trials and tribulations and comes out good in the end. If you don’t already own it, it’s one worth adding to the shelf.

3. Private Parts (1997)

Howard Stern’s outrageous rise from awkward radio DJ to national shock-jock superstar is retold here in a film that’s equal parts biography and comedy. Private Parts blends genuine heart with raw, uncensored humour — and even if you’ve never listened to Stern, it’s hard not to be pulled into his story. A strange mix of honesty, absurdity, and self-mockery that somehow just works.

My 2 Cents: I first saw this movie years ago and it was very funny. I introduced it to my adult son a few years ago and he got a great kick out of it too. It’s about that time to dust off the jewel case and give it another spin.

4. Wedding Crashers (2005)

John Beckwith (Owen Wilson) and Jeremy Grey (Vince Vaughn) have mastered the art of crashing weddings — free food, free drinks, and endless romantic opportunities. But when one of them actually falls in love, their game starts to unravel. Smartly written and endlessly quotable, Wedding Crashers has aged surprisingly well and still delivers genuine belly laughs.

My 2 Cents: Owen and Vince were on top of their game when this one was made. A hilarious comedy and one I still come back to every year or so. It still hits all the right notes after all these years, and every rewatch reminds me why it became a classic.

5. Kingpin (1996)

Woody Harrelson plays Roy Munson, a washed-up bowling prodigy who discovers a naïve Amish talent (Randy Quaid) with a golden arm. Together they set out to win a major tournament and face off against Roy’s sleazy rival, played by Bill Murray at his absolute best. Equal parts crude, absurd, and oddly heartwarming, Kingpin is a perfect example of why the Farrelly Brothers ruled 90s comedy.

My 2 Cents: This comedy certainly wouldn't be made today in our politically correct world, more's the pity. There are plenty of laugh-out-loud moments as Roy chases riches and fame, only to rediscover the dignity he thought he’d lost years earlier. A great comedy with a surprisingly heartfelt ending — definitely one for your collection.

Final Thoughts

Comedy’s a funny thing, what makes one person cry laughing might leave another scratching their head. But these five have stood the test of time for me. They’re the kind of films I can throw on any night and still laugh at every single scene. If you haven’t seen them in a while (or ever), do yourself a favour: grab a drink, kick back, and press play.

Thanks for Reading,

David

💬 Have a thought on this? Please leave a comment below, I’d love to hear your take.

About the Author

I’m David Condon, a movie enthusiast from Tralee, Co. Kerry. I’ve been collecting DVDs and Blu-rays for years, and along the way my shelves have become a mix of favourites, hidden gems, and titles I occasionally decide to resell.

I’m not a professional critic — just someone who enjoys good films, well-made discs, and the odd rant about the quirks of collecting. This blog is where I share my thoughts, opinions, reviews, and experiences as a fan.

💬 Note from the Author
This blog is a hobby project where I write about DVDs, Blu-rays, and the ups and downs of being a collector. If you enjoyed this post, you might also like my other writing:

David Condon Finds – my lifestyle and review blog
David Condon Woodcraft – my main website focused on woodturning and handmade pieces

If you’d like to support the blog, you can do so through the Buy Me a Coffee button below. It helps keep this little side project alive — thank you!

Search This Blog

Phoenix DVD Blog