Best Comedy Films of 1995
- HaHa Jokester
- Jun 16
- 7 min read
Updated: Jun 20
1995 was a year of stylistic variety and generational shifts in comedy. From teen sarcasm and animated toys to workplace satire and rom-com charm, the genre evolved alongside a changing audience. The loud slapstick of the early ’90s gave way to quirkier, character-driven stories, and indie comedy began to creep into the mainstream. It was a year where cleverness mattered as much as laughs.
The Comedy Landscape in 1995
Teen Culture Takes Center Stage
Clueless wasn’t just a hit—it redefined teen comedies with style, smarts, and valley-girl flair that would influence a decade of high school movies.
Animation for All Ages
Toy Story became the first fully computer-animated feature and proved that great writing and clever humor could entertain both kids and adults.
Work, Identity & Existential Laughs
Films like Living in Oblivion and Kicking and Screaming tackled creative struggle and post-college angst with biting, reflective humor.
Top 10 Comedy Films of 1995
Clueless
Runtime: 1hr 37min
A wealthy, fashion-forward teen in Beverly Hills plays matchmaker but discovers love and self-awareness in the process.
In Clueless, Cher Horowitz (Alicia Silverstone), a charming yet superficial high schooler, reigns over her Beverly Hills social circle with wit and style. Inspired by a sense of goodwill (and her own ego), she transforms a new student’s life, plays matchmaker for teachers, and doles out fashion advice, all while remaining oblivious to her own romantic feelings. Loosely based on Jane Austen’s Emma, the film cleverly satirizes teen culture while offering heartfelt growth and timeless quotability.
Toy Story
Runtime: 1hr 21min
When a cowboy doll feels threatened by a flashy new space toy, an unexpected adventure teaches them both the value of friendship.
Toy Story, the first fully computer-animated feature film, follows Woody, a pull-string cowboy, whose position as favorite toy is challenged when Buzz Lightyear, a high-tech space ranger, joins the toy box. Their rivalry leads to mishaps that separate them from their owner, Andy, forcing them to work together to find their way home. Blending heart, humor, and groundbreaking visuals, this Pixar classic explores themes of jealousy, identity, and loyalty while revolutionizing animated storytelling.
Tommy Boy
Runtime: 1hr 35min
A lovable screw-up and his uptight partner go on a chaotic road trip to save the family business.
In Tommy Boy, the bumbling but big-hearted Tommy Callahan (Chris Farley) inherits his father’s struggling auto parts company and teams up with the straight-laced Richard (David Spade) to sell brake pads across the country. Their mismatched partnership leads to physical comedy, wild mishaps, and unexpected growth as Tommy learns to believe in himself. A cult favorite, the film thrives on the electric comedic chemistry between Farley and Spade and blends slapstick with surprising sincerity.
Friday
Runtime: 1hr 30min
Two friends spend a wild day in South Central L.A. dealing with debts, neighborhood drama, and hilarious misadventures.
Friday centers on Craig (Ice Cube), who gets fired on his day off, and his fast-talking friend Smokey (Chris Tucker), who owes a drug dealer money. As the two navigate their eccentric neighborhood, they encounter a parade of colorful characters and escalating problems, all within the span of one Friday. Mixing comedy with social commentary, the film became a touchstone for urban storytelling and launched a beloved trilogy known for its humor, heart, and quotable dialogue.
The American President
Runtime: 2hr 9min
A widowed U.S. President falls in love with a lobbyist, complicating both his personal life and political career.
In The American President, President Andrew Shepherd (Michael Douglas) is a popular widower whose budding romance with environmental lobbyist Sydney Ellen Wade (Annette Bening) causes public and political turmoil. As their relationship unfolds under media scrutiny, Shepherd must balance national interests with personal happiness. Directed by Rob Reiner and written by Aaron Sorkin, the film blends romantic comedy with political drama, offering charm, sharp dialogue, and a precursor to The West Wing’s tone and style.
While You Were Sleeping
Runtime: 1hr 43min
A lonely transit worker saves her crush and gets mistaken for his fiancée—only to fall for his brother.
While You Were Sleeping stars Sandra Bullock as Lucy, a Chicago transit worker who rescues a man she secretly admires from an oncoming train. When his family believes she's his fiancée during his coma, Lucy gets swept up in their warm embrace—and inadvertently falls for his skeptical brother. This romantic comedy thrives on mistaken identity, heartfelt emotion, and Bullock’s relatable charm, becoming a holiday favorite and a key entry in the ‘90s rom-com canon.
Billy Madison
Runtime: 1hr 28min
A spoiled man-child must redo grades 1–12 to inherit his father’s company.
In Billy Madison, Adam Sandler plays an immature slacker whose wealthy father challenges him to prove he's capable of running the family business by redoing every grade of school. Billy’s absurd, juvenile antics turn each classroom into a comedic playground, but he gradually matures through friendships, competition, and romance. Ridiculous, quotable, and filled with surreal humor, the film cemented Sandler’s status as a comedy star and kicked off a wave of similarly zany comedies.
To Die For
Runtime: 1hr 46min
An ambitious weather reporter stops at nothing—including murder—to become a famous TV personality.
Nicole Kidman stars in To Die For as Suzanne Stone, an aspiring media personality so obsessed with fame that she manipulates a group of teenagers into murdering her husband. Darkly satirical and chillingly comedic, the film dissects America’s celebrity culture and the dangers of unchecked ambition. With sharp direction from Gus Van Sant and a standout performance by Kidman, it blends mockumentary style and noir elements into a smart, disturbing, and wickedly funny tale.
Get Shorty
Runtime: 1hr 45min
A smooth-talking loan shark tries his hand at Hollywood and discovers crime and showbiz aren’t so different.
In Get Shorty, John Travolta plays Chili Palmer, a Miami loan shark whose trip to collect a debt in Los Angeles evolves into a comically successful attempt to produce a Hollywood movie. Navigating mobsters, actors, and egos, Chili’s criminal savvy proves perfectly suited to the absurdities of the film industry. With a sharp Elmore Leonard script, slick direction, and a charismatic lead, the film satirizes both crime thrillers and Hollywood with style and wit.
Mallrats
Runtime: 2hr 3min
Two slackers hang out at the mall after being dumped and stumble into chaos, comic books, and love.
Kevin Smith’s Mallrats follows Brodie and T.S., two comic book-loving underachievers, who seek solace in their local mall after being dumped by their girlfriends. What follows is a chaotic day filled with eccentric characters, pop culture rants, and a game show sabotage. Packed with nerdy references, raunchy humor, and early appearances by Jason Lee and Ben Affleck, the film has since become a cult classic and an early cornerstone of the View Askewniverse.
Underrated Picks Worth Your Time
Living in Oblivion
Runtime: 1hr 32min
A brilliant indie satire about the chaos of low-budget filmmaking—Steve Buscemi delivers peak neurotic genius in a world of collapsing sets and broken dreams.
Living in Oblivion is a sharp, surreal indie comedy that satirizes the chaos of low-budget filmmaking. Directed by Tom DiCillo, the film follows director Nick Reve (Steve Buscemi) as he tries to complete a seemingly simple scene—only to be thwarted by technical glitches, egotistical actors, insecure crew members, and his own creeping doubts. Told in three segments that blur the line between dreams and reality, the film hilariously captures the tension, absurdity, and fragile egos that plague film sets, offering a love letter and a critique of the independent film world all at once.
Kicking and Screaming
Runtime: 1hr 36min
Noah Baumbach’s debut is a razor-sharp, talky exploration of post-college paralysis, filled with deadpan humor and academic detachment.
Kicking and Screaming, Noah Baumbach’s debut film, is a witty and melancholic comedy about a group of recent college graduates who, paralyzed by uncertainty and nostalgia, refuse to move on with their lives. Centered around Grover (Josh Hamilton) and his friends, the film explores post-graduate aimlessness as the characters linger near campus, debating literature, clinging to old routines, and fearing the responsibilities of adulthood. With sharp dialogue, dry humor, and a deep undercurrent of existential unease, it captures the bittersweet transition between youth and maturity with both affection and biting honesty.
The Brady Bunch Movie
Runtime: 1hr 30min
This meta-parody of the wholesome ’70s TV family drops them into cynical ’90s L.A.—and the result is surprisingly hilarious and self-aware.
The Brady Bunch Movie is a clever and absurdist comedy that transports the iconic 1970s TV family into the cynical, grunge-filled world of the 1990s. As the Brady clan—perpetually wholesome, fashionably outdated, and cheerfully oblivious—struggles to save their house from foreclosure, their retro values hilariously clash with modern-day culture. Featuring deadpan performances, self-aware humor, and spot-on recreations of the original show's quirks, the film parodies both the Brady legacy and the era’s ironic detachment, resulting in a nostalgic yet sharply satirical take on sitcom innocence.
Comedy Highlights & Trivia
Welcome to Sherwood… Again
Clueless, loosely based on Jane Austen’s Emma, proved that timeless story structures could power modern, youth-driven comedy gold.
“You Are a Toy!”
Toy Story became the highest-grossing comedy of the year and launched Pixar as a creative powerhouse in animation and storytelling.
Chris Farley & David Spade = Comedy Gold
Tommy Boy established Farley as a comedic force with heart, slapstick, and an underdog’s soul—anchored by Spade’s perfect dry delivery.
Where to Watch These Today
Clueless – Paramount+, Netflix
Toy Story – Disney+
Tommy Boy – Netflix, Paramount+
Friday – Max, Hulu
Billy Madison – Peacock, Amazon
Get Shorty – Prime Video
To Die For – Tubi, Apple TV
Living in Oblivion – Criterion Channel
Kicking and Screaming – Criterion Channel, Apple TV
To Wong Foo – Netflix, Starz
Closing Thoughts
1995 marked the maturation of ’90s comedy. It wasn't just about big laughs anymore—it was about identity, tone, and clever reinvention. From the heartfelt charm of Toy Story to the biting satire of To Die For, and the cult legacy of Mallrats, the year's comedies embraced both edge and sincerity. It was a turning point—a year when comedy got smarter, stranger, and more varied, laying the groundwork for the rest of the decade.
