10 Criminally Underrated Comedy Movies From the Last 30 Years

10 Criminally Underrated Comedy Movies From the Last 30 Years

Streaming has made it easier than ever to find something funny, but it’s also made it easier for genuinely great comedies to get buried under whatever’s trending this week.

Over the last 30 years, plenty of laugh-out-loud movies landed with critics, built small cult followings, or quietly won over anyone who stumbled onto them at the right time, yet they never became the endlessly quoted “everyone has seen it” classics.

Sometimes the marketing was off, sometimes they opened against a juggernaut, and sometimes audiences just weren’t ready for the tone.

Either way, these movies deserve better reputations than they have, because the jokes still hit, the performances are ridiculously committed, and the rewatch value is real.

If you’re in the mood to feel like you discovered something, these criminally underrated comedies are a perfect place to start.

1. The Man Who Knew Too Little (1997)

A harmless birthday gift turns into the kind of chaos that only Bill Murray can glide through like it’s no big deal.

He plays a guy who thinks he’s participating in an immersive “spy game,” so every real threat looks like part of the entertainment package he paid for.

That misunderstanding becomes a comedy engine, because his relaxed confidence keeps colliding with very serious people who have no idea why this clueless tourist is ruining their plans.

The movie is lighter than a gritty espionage parody, but it’s smarter than its reputation suggests, especially in how it uses timing and miscommunication instead of cheap punchlines.

Murray’s charm does a lot of heavy lifting, yet the supporting cast sells the stakes just enough to keep the absurdity grounded.

It’s the ideal pick when you want steady laughs without something overly loud or exhausting.

2. Dirty Work (1998)

Revenge plots usually sound satisfying in theory, but this movie makes them look like the messy, ridiculous disasters they’d be in real life.

Norm Macdonald and Artie Lange play two lovable screwups who start a business where they get payback for people who’ve been wronged, which immediately spirals into petty schemes and spectacular misfires.

The humor is broad and proudly immature, yet it stays weirdly charming because Norm’s deadpan delivery makes every stupid idea feel oddly reasonable.

The movie also has that late-’90s vibe where side characters show up, steal scenes, and disappear like a comedy drive-by, keeping the pace fast even when the plot is gleefully all over the place.

If you miss comedies that feel like they were made to make the cast laugh as much as the audience, this one still holds up.

3. Bowfinger (1999)

Desperation has rarely been this funny, especially when it’s aimed directly at Hollywood’s weirdest habits.

Steve Martin plays a broke, scheming filmmaker who decides to “cast” a megastar without his knowledge, secretly filming him in real life and building a movie around whatever footage he can steal.

Eddie Murphy is incredible in dual roles, playing both the paranoid celebrity and his sweet, awkward lookalike, which gives the story both chaos and unexpected warmth.

The satire works because it’s exaggerated but uncomfortably plausible, like the movie is only a few degrees away from something that could actually happen.

Every time you think the plan has peaked, it escalates into an even worse idea, and the script keeps the jokes sharp without losing momentum.

It deserves to be talked about in the same breath as the biggest comedy classics from its era.

4. Saving Silverman (2001)

A friendship intervention turns into a full-blown mission here, and the movie commits so hard to the premise that it becomes impossible not to laugh at the escalating nonsense.

Jack Black and Steve Zahn play two best friends who are convinced their buddy is being controlled by a domineering girlfriend, so they attempt increasingly unhinged plans to “rescue” him.

What makes it work is the chemistry, because their panic feels like genuine loyalty even when their decisions are completely unhinged.

The tone is shamelessly early-2000s, meaning everyone is loud, emotions are big, and logic is basically banned from the set, but that’s also part of its charm.

It’s the kind of comedy that’s best enjoyed when you stop asking whether any of it makes sense and just let the chaos roll.

If you like movies that feel like a rowdy group hang, this one is a wildly underrated rewatch.

5. Big Trouble (2002)

An innocent situation explodes into a chain reaction of misunderstandings, and watching it snowball is exactly the point.

The movie juggles a big ensemble where every character’s bad decision bumps into someone else’s bad decision, creating a farce that keeps tightening like a knot.

A mysterious suitcase, incompetent criminals, confused bystanders, and a series of unfortunate coincidences all collide in a way that feels carefully constructed, even when it looks like pure madness.

The best laughs come from how seriously everyone takes themselves, because the actors play their confusion straight while the plot keeps getting more ridiculous.

It’s also a great example of a comedy that doesn’t pause to over-explain, trusting you to keep up as storylines cross and crash into each other.

If you love “everything goes wrong” movies that feel like controlled chaos, this one is criminally overlooked.

6. The In-Laws (2003)

Meeting the family is stressful enough without accidentally marrying into an action movie.

Albert Brooks plays a tightly wound, anxious guy who wants a normal wedding, while Michael Douglas shows up as the kind of future father-in-law who treats danger like a fun hobby.

The comedy hits because Brooks reacts the way any reasonable person would, which is basically constant disbelief mixed with rising panic, and Douglas plays his chaos with effortless charm.

Their contrast makes every scene feel like a tug-of-war between sanity and swagger, and the script keeps the pace moving so it never drags.

It’s not trying to reinvent comedy; it’s aiming to entertain you for two hours, and it succeeds with ease.

If you want something light, funny, and way more charming than people remember, this is a great underrated pick.

7. Kiss Kiss Bang Bang (2005)

A messy, accidental reinvention of oneself powers this movie, and it blends comedy with noir-style mystery in a way that still feels fresh.

Robert Downey Jr. plays a small-time crook who stumbles into Hollywood and ends up tangled in a case he barely understands, while Val Kilmer steals scenes as a sharp, brutally honest private investigator who seems allergic to nonsense.

The dialogue crackles, the narration is cleverly self-aware, and the jokes land because they come from character dynamics rather than forced punchlines.

What makes it especially rewatchable is how many lines are funny on first listen and even funnier once you know the story beats.

It’s slick without being smug, dark without being depressing, and genuinely hilarious without needing to go broad.

If you like comedies that make you feel smart while you’re laughing, this one is an easy 10/10 that deserves a much louder legacy.

8. Hamlet 2 (2008)

A midlife crisis becomes strangely inspiring here, even as the movie leans into humor that’s gloriously inappropriate and proudly chaotic.

Steve Coogan plays a washed-up actor turned high school drama teacher who decides to write an original play that he believes will be his masterpiece, even though it’s obviously an unhinged disaster.

The funniest moments come from the gap between his confidence and his talent, yet the movie also treats the students like real people instead of disposable punchlines.

As the production grows bigger and more ridiculous, the story becomes unexpectedly sweet, turning into a weird little celebration of trying anyway when life didn’t go according to plan.

It’s bold, awkward, and oddly heartfelt, which is probably why it didn’t become a mainstream favorite.

If you’re tired of safe comedies, this one is a delightfully underrated curveball.

9. Popstar: Never Stop Never Stopping (2016)

A celebrity meltdown has never been this densely hilarious, largely because the movie crams jokes into every corner like it’s afraid you might blink and miss one.

The story follows a pop star whose solo career starts unraveling in spectacularly embarrassing fashion, and it nails the modern fame vibe where everything is overproduced, overhyped, and one bad headline away from disaster.

Andy Samberg is perfect as someone who’s genuinely talented but also completely delusional, and the cameos actually add to the comedy instead of distracting from it.

The mockumentary format works because it feels both ridiculous and painfully accurate, especially when it skewers image management, manufactured authenticity, and ego spirals.

What makes it a 10/10 rewatch is that it hits on multiple levels at once—visual gags, music jokes, cringe comedy, and sharp satire—while still landing as a story about friendship and identity when the spotlight isn’t flattering anymore.

10. The Nice Guys (2016)

A missing-person case shouldn’t be this funny, but this movie turns detective work into a constant parade of mistakes, bad timing, and accidental heroism.

Ryan Gosling plays a barely functional private investigator whose panic-prone energy becomes the comedic heartbeat of the film, while Russell Crowe grounds everything as his tougher, more competent counterpart.

Their reluctant partnership is the real magic, because the movie lets them bicker, fail, and improvise their way through danger like two guys who absolutely should not be trusted with anything important.

The humor is sharp, the action is clean, and the ’70s setting adds a layer of sleazy charm without feeling like a gimmick.

It also has that rare quality where the jokes don’t undercut the story; they make the story more fun to watch.

If you somehow missed it, it’s one of the most criminally underrated studio comedies of the last decade.