These 10 Hilarious Comedies From The 1990s Never Got Enough Love

The 1990s were such a great period for comedy movies that there are plenty of great films from this era that never quite got their due. While this was the time when stars like Adam Sandler, Jim Carrey, and Mike Myers released some of their best movies, plenty of talented comedians also led hilarious films that did not hit big at the box office or gain the sort of long-standing cultural relevance as things like Happy Gilmore, Ace Ventura, or Austin Powers. For every blockbuster comedy, there’s another underappreciated, hidden gem just waiting to be discovered.

Some of the best comedies of the 1990s never got enough love and have now been wallowing in obscurity for decades. Luckily, in the age of the internet and streaming, it’s easy to go back and rediscover a lost classic and give a misunderstood film its due well after the fact. While none of these films had achieved the kind of outstanding cultural impact as the most popular comedies of the 1990s, they were still laugh-out-loud hilarious and deserve more attention.

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10

Grumpy Old Men (1993)

Directed by Donald Petrie

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Grumpy Old Men

PG-13

Comedy

Release Date

December 25, 1993

Runtime

103 minutes

Cast

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• 

  Jack Lemmon

  John Gustafson

• 

  Walter Matthau

  Max Goldman

• 

  Ann-Margret

  Ariel Truax

• 

  Kevin Pollak

  Grandpa Gustafson

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Screen legend Jack Lemmon reunited with his frequent collaborator and his Odd Couple co-star Walter Matthau for a light-hearted comedy about two neighbors with a long-standing rivalry. Proving that the duo hadn’t lost any of their incredible onscreen chemistry, the pair’s ill will toward one another only intensified when a new female neighbor moved in across the street. While Lemmon and Matthau had funnier collaborations in the past, it was delightful to see them share the screen once again in this enjoyable comedy that just doesn’t get enough love.

With Lemmon and Matthau both in their 60s, it was hilarious to see the two bickering like teenagers in a holiday movie that’s sure to brighten the day of even the most cynical viewers. Grumpy Old Men was an age-appropriate role that put its elderly stars front and center and was even successful enough to get a sequel, Grumpier Old Men, in 1995. However, by that stage, the joke had run dry, and it just did not have nearly the same appeal.

9

Black Sheep (1996)

Directed by Penelope Spheeris

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Black Sheep

PG-13

Comedy

8/10

3/10

Release Date

February 1, 1996

Runtime

87 Minutes

Cast

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• 

  Chris Farley

• 

  David Spade

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Director Penelope Spheeris had previously found success working with Saturday Night Live alumni on Wayne’s World and decided to team up with Lorne Michaels once again for Black Sheep. With Chris Farley and David Spade in the lead roles, this hilarious comedy depicted a political aide’s attempts to control the brother of a candidate for Governor of Washington. While Farley and Spade’s buddy comedy from the previous year, Tommy Boy, had more laughs than Black Sheep, this underrated release still deserves far more attention.

With plenty of juvenile humor and some predictable setups, Black Sheep was a broad comedy that depended entirely on the chemistry between its two main stars. Luckily, Spade and Farley knew how to deliver, and for those looking to enjoy a glimpse into the often silly excesses of 1990s comedy movies, this film will be exactly what you’ve been searching for. Black Sheep wasn’t groundbreaking, but it definitely should be far more recognizable than it is.

8

Soapdish (1991)

Directed by Michael Hoffman

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Soapdish

PG-13

Comedy

Romance

Release Date

May 31, 1991

Runtime

97 minutes

Cast

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• 

  Sally Field

• 

  Kevin Kline

• 

  Robert Downey Jr.

• 

  Cathy Moriarty

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While Soapdish was well-received at the time, modern viewers have mostly forgotten this satirical comedy. This was a real shame, as this backstage story explored the comedic chaos and behind-the-scenes antics of a daytime soap opera and all the outrageous rivalries, double-crossing, and subtle resentments that build up in the dog-eat-dog world of show business. With a fantastic lead performance from Sally Field and appearances from the likes of Robert Downey Jr., Whoopi Goldberg, and Carrie Fisher, plenty of A-list comedic talent helped make this a laugh-out-loud spoof of the life behind the small screen.

By tapping into the jealousy and resentment of these soap opera actors, Soapdish showcased the genre’s sheer ridiculousness and melodramatic nature. With the perfect balance of clever humor and zany performances, something interesting was constantly happening on screen, and the movie was just plain fun to watch. Although Soapdish never quite got the love it deserved, a TV adaptation was first announced in 2022 (via Deadline), so perhaps the viewers will go back and discover its appeal when it finally makes it to air.

7

Bottle Rocket (1996)

Directed by Wes Anderson

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Bottle Rocket

R

Comedy

See more : 10 Movies That Break The Fourth Wall In Brilliantly Inventive Ways

Crime

Drama

Release Date

February 21, 1996

Runtime

91 Minutes

Cast

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• 

  Luke Wilson

• 

  Owen Wilson

• 

  Robert Musgrave

• 

  Lumi Cavazos

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While Wes Anderson has built up a reputation for himself as one of the most beloved, idiosyncratic, and quirky directors of modern times, his debut movie, Bottle Rocket, never quite got the attention it deserved. Although this unique crime comedy, co-written by Anderson and its star Owen Wilson, was an early indication of the director’s unique visual flair, as his minimalist and carefully constructed style had yet to emerge. This meant Bottle Rocket was an enjoyable glimpse into Anderson’s creative process and highlighted a more raw, freewheeling version of the future master of composition.

Bottle Rocket told the story of three friends planning to commit the perfect robbery, although they had no idea just how ill-prepared they were for pulling off a clever heist. With plenty of deadpan, awkward humor, Anderson poked fun at the crime genre while also ensuring his dim-witted characters acted with total sincerity. Bottle Rocket was an accomplished, if uneven, directorial debut, and it deserves to be remembered alongside the likes of Rushmore and The Grand Budapest Hotel as an essential addition to Anderson’s acclaimed filmography.

6

It Could Happen To You (1994)

Directed by Andrew Bergman

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It Could Happen to You

PG

Romance

Comedy

Drama

Release Date

July 29, 1994

Director

Andrew Bergman

Cast

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• 

  Nicolas Cage

• 

  Bridget Fonda

• 

  Rosie Perez

• 

  Wendell Pierce

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Nicolas Cage was one of the defining actors of the 1990s, and, alongside all-time great action movies like Con Air and Face/Off, he starred in some great comedies. Among these was It Could Happen to You, the story of a New York cop who half-jokingly promised his waitress that if he won the lottery. While this seemed like a fickle promise that had less than a one-in-a-million chance of coming true, it actually happened, and Charlie Lang made good on his promise to give up half of his $4 million prize to a woman he had only just met.

It Could Happen to You felt like the kind of larger-than-life rom-com story that only happens in the movies, yet this underrated film was inspired by a real news story (via EW.) While Cage has become known for outrageous and often over-the-top performances, he was never sweeter than as this honest cop who stays true to his word.

5

Defending Your Life (1991)

Directed by Albert Brooks

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Defending Your Life

PG

Comedy

Fantasy

Romance

Drama

Release Date

March 22, 1991

Runtime

111 minutes

Cast

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• 

  Albert Brooks

  Daniel Miller

• 

  Meryl Streep

  Julia

• 

  Rip Torn

  Bob Diamond

• 

  Lee Grant

  Lena Foster

Defending Your Life follows advertising executive Daniel Miller, who, after dying suddenly, arrives in Judgment City where the dead must justify their life choices to progress further. While grappling with self-doubt, Daniel encounters Julia, whose influence helps him confront his fears and embrace life more fully.

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The Academy Award-winning actor Albert Brooks has also written and directed plenty of great, underrated comedies, with Defending Your Life being one of his most underappreciated works. Telling the story of a man who finds himself on trial in the afterlife, Brooks played Daniel Miller, an advertising executive who must convince a group of condescending bureaucrats in Judgement City that he’d made enough of his life on Earth to be allowed to move onto the next phase of existence, rather than be reincarnated yet again.

With an insanely clever premise, Defending Your Life captured all the appeal of TV series like The Good Place decades before it was even released. With a smart script that highlighted the value of making the most out of our brief time on Earth, Defending Your Life was a funny reminder of the pointlessness of acting out of fear and not following our hopes, dreams, and ambitions. With an extraordinary 98% on Rotten Tomatoes, Defending Your Life was extremely well received by those who have seen it, but it’s woefully underknown by the average viewer.

4

Half Baked (1998)

Directed by Tamra Davis

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Half Baked

R

Comedy

See more : 10 Movies That Break The Fourth Wall In Brilliantly Inventive Ways

Crime

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10/10

Release Date

January 16, 1998

Runtime

82 minutes

Cast

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• 

  Dave Chappelle

• 

  Guillermo Diaz

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While Half Baked was dismissed by critics for its sheer stupidity at the time of its release, this was part of the reason this stoner comedy has been a quiet cult classic in the marijuana community. Telling the story of four lifelong friends with a love for a certain plant, Half Baked saw these weed enthusiasts forced into action as they came up with elaborate schemes to get their friend out of jail after he accidentally fed a diabetic horse too much junk food. With Dave Chappelle excelling in the lead role, this stoner classic was unfairly panned back in 1998.

It’s true that Half Baked embraced dumb and silly humor, but what more could you expect from a stoner comedy. This was the perfect film to sit back and howl with laughter at with a group of friends, as its laid-back energy and cartoonish logic embrace its own absurdity. With enjoyable cameos from the likes of Snoop Dogg and Bob Saget, Half Baked’s slapstick antics, one-liners, and surreal humor meant it was endlessly rewatchable, assuming you’re in the right state of mind to enjoy something so silly.

3

Blast From The Past (1999)

Directed by Hugh Wilson

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Blast from the Past

PG-13

Comedy

Drama

Romance

Release Date

February 12, 1999

Runtime

112 minutes

Cast

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• 

  Brendan Fraser

• 

  Alicia Silverstone

• 

  Christopher Walken

• 

  Sissy Spacek

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Blast from the Past was a clever comedy about a modern man whose sheltered upbringing in a bomb shelter meant that he was raised entirely on 1950s pop culture. With Brendan Fraser as the clueless Adam Webber, this man’s eccentric father’s belief in a nuclear war meant he was born in a fallout shelter and didn’t get to see the outside world for 35 years. While this intriguing premise brought to mind the video game Fallout, rather than find himself in a post-apocalyptic world, when Adam finally got out, he realized there never was any civilization-ending event at all.

Despite the traumatic implications of Adam’s life circumstances, Blast from the Past was a hilarious comedy with Fraser giving a great performance as a man without any knowledge of the previous decades’ culture. Despite a smart script from Hugh Wilson and Bill Kelly, Blast from the Past underperformed at the box office and has mostly been forgotten by viewers. This was a real shame, as the film’s sly satire was incredibly clever, and this unique fish-out-of-water story provided some big laughs.

2

What About Bob? (1991)

Directed by Frank Oz

What About Bob?

PG

Comedy

Release Date

May 17, 1991

Runtime

100 minutes

Cast

• 

  Bill Murray

  Bob Wiley

• 

  Richard Dreyfuss

  Dr. Leo Marvin

• 

  Julie Hagerty

  Fay Marvin

• 

  Charlie Korsmo

  Sigmund “Siggy” Marvin

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While the Muppet puppeteers Frank Oz’s directorial works, such as The Dark Crystal and Little Shop of Horrors, have rightfully gained devoted fanbases, his 1990s comedy What About Bob? is rarely part of the conversation of his best works. Without the fantastical elements that are usually associated with Oz, this underseen Bill Murray comedy seems to be consistently forgotten about. However, What About Bob? remains truly hilarious as Murray’s performance as a mentally unstable patient following his psychotherapist on vacation hit all the right notes.

Richard Dreyfuss made an excellent straight man to the neurotic, obsessive, but oddly lovable antics of Murray’s character. By flipping the usual therapist-patient dynamic to have the medical professional on the verge of insanity, What About Bob? showcased that there’s a limit to therapists’ patience, as Bob’s actions slowly pushed Dr. Leo Marvin toward the brink of a mental breakdown. As an excellent 1990s film that never quite gets the attention it deserves, viewers should go back and check out What About Bob?

1

Romy And Michele’s High School Reunion (1997)

Directed by David Mirkin

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Romy and Michele’s High School Reunion

R

Comedy

7.2/10

Release Date

April 25, 1997

Runtime

92 Minutes

Cast

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• 

  Mira Sorvino

• 

  Lisa Kudrow

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Everyone wants to show off just how successful and fulfilled they are at their high school reunion, and Romy and Michele’s High School Reunion took this desire to the absolute extreme. With Oscar-winner Mira Sorvino and Friends star Lisa Kudrow in the title roles, this underrated comedy boasted some serious star talent yet never seemed to get its due as one of the funniest comedies of the 1990s. Through a story about two women who have not achieved much in life, orchestrating an elaborate lie for their ten-year school reunion, this cult classic will have you crying with laughter.

Romy and Michele’s High School Reunion was wickedly funny, but this comedy was also elevated by its strong characterization and subtle emotional depth underpinning its story. Although Romy and Michele’s lives were total disasters, they could always rely on one another, and themes of friendship and loyalty powerfully came to the forefront. With an ingenious plan to pretend they became successful by inventing Post-It notes, Romy and Michele’s High School Reunion was as funny as it was totally ridiculous.

Sources: Deadline, EW

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Category: Entertainment