15. Clueless (1995)
“As if!” Writer/director Amy Heckerling (Fast Times at Ridgemont High) had a charming hit on her hands––one that would spawn a series of YA books and a short-lived TV sitcom––with her Jane Austen-inspired (think “Emma”) coming-of-age comedy Clueless. Starring a scorchingly hot teen starlet Alicia Silverstone––she was huge at the time thanks to the music video for Aerosmith’s “Cryin’”––as the shallow, sheltered, and very privileged high school pris Cher Horowitz.
The most popular and superficial socialite Valley Girl-type at her Beverly Hills high school, she finds success as a matchmaker after hooking up two lovesick teachers, Mr. Hall (Wallace Shawn) and Miss Geist (Twink Caplan) and soon finds herself trying to either fix or play cupid with everyone in her orbit.
The game cast includes Stacey Dash, Brittany Murphy, and Paul Rudd, the soft satire and social insights are easy to digest and all quite enjoyable, adding up to a surprisingly fun, and at times even profound, insight into contemporary teen life. “As if!”
14. Austin Powers: International Man of Mystery (1997)
The 1990s were very good to amicable funnyman Mike Myers, and while some of his jokes haven’t aged well, it’s fair to say that elated outcries of “Yeah, baby!” and “One million dollars!” were repeated ad nauseum and with oomph ever since his world-class playboy with horrible teeth and menacing adversary first hit the silver screen.
This playful pisstake on the swinging 60s and the James Bond mythos was fresh and invigorating back in 1997, and viewed today some 20 years later a lot of the jokes are still surprisingly sharp.
International playboy and touted “Man of Mystery” Austin Powers (Myers) is a special agent who was cryogenically frozen for 30 years, defrosted to go up against his diabolical nemesis Dr. Evil––also played by Myers.
Still stuck in the rampant free love sexuality of yesteryear, Austin’s old school mindset comes into conflict with his attractive new sidekick, agent Vanessa Kensington (Elizabeth Hurley), meanwhile Dr. Evil is at odds trying to relate to his teenaged Gen X son, Scott Evil (Seth Green), while plotting world domination via “Project Vulcan” and amassing a new slough of vile henchman (including Will Ferrell, Mindy Sterling, and Robert Wagner).
Better than all the sequels that came after, Austin Powers, for all his horny foibles and well-timed zingers, is terribly hard to resist. “Ooo, Behave!”
13. Welcome to the Dollhouse (1995)
Todd Solondz’s second feature as writer-director is the bitterly amusing coming-of-age black comedy Welcome to the Dollhouse––his first feature film was 1989’s little seen musical comedy Fear, Anxiety & Depression––and it was the toast of Sundance in ‘95, where it took home the Grand Jury Prize.
Set in one of writer-director Solondz’s favorite locales, middle-class suburbia, Welcome to the Dollhouse unrolls amidst a New Jersey adjacency where a ruthlessly teased middle-school student, eleven-and-a-half-year-old Dawn Wiener (Heather Matarazzo) lives.
Painfully shy and reluctantly nicknamed “Wiener Dog” by her peers, Dawn is the middle child caught between her snobby nerd of an older brother Mark (Matthew Faber) and her fawned over little sister Missy (Daria Kalinina), with little room for herself to fit in and be a pre-teen.
A frequently dark and often times cruel tale of 7th-grade exploitation––this is a Solondz film, after all––Dawn isn’t always portrayed in a sympathetic or even pleasant light. She’s rather flawed, and frequently contentious, even when being harassed and hazed by her tormentor Brandon (Brendan Sexton III). A critically lauded picture, and something of a sleeper, this is a quirky and rather cold-blooded account of the awkward stage before adulthood, told with provocation and spite, yet guiltily as amusing as it is mean.
12. Mrs. Doubtfire (1993)
What could easily be a treacly, over sentimental snore, or a carbon-copy of Tootsie (1982) with a dash of Some Like it Hot (1959) winds up being a delightful, madcap, cross-dressing romp thanks largely to Robin Williams’ winning performance as divorced dad Daniel Hillard.
Granted, for Mrs. Doubtfire to work you’ve got to suspend disbelief––the same way you would for the aforementioned films or any broad screwball farce––and just go with it.
With assured direction from prolific and populist director Chris Columbus (Adventures in Babysitting, Home Alone), Mrs. Doubtfire dives into the life of our troubled protagonist Daniel, and his upset that he sees so little of his children now that he and his ex-wife Miranda (Sally Field) have gone their separate ways.
Leaning on his creative makeup artist brother Frank (Harvey Fierstein), he adopts the alter ego of Scottish nanny Mrs. Euphegenia Doubtfire to win over his estranged kids and become a better person overall. That thin premise ends up going pretty far as the gags, white lies, and erstwhile shenanigans escalate. That it all works out in the end is of no surprise, but the irresistible charms of this often OTT comedy will surprise even the most jaded audience member.
11. Office Space (1999)
Writer-director Mike Judge (of Beavis and Butt-head fame) made his live-action directorial debut with this workplace satire Office Space that, while originally just a minor success, is today thought of as an influential cult classic as well as a fond social artifact of the late-90s experience.
Ron Livingston (Swingers) is corporate drone Peter Gibbons, bitter about his soul-sucking job at Initech, a thankless software company. One day while undergoing hypnotherapy from his therapist Dr. Swanson (Mike McShane), Peter gets into a Zen-like state of euphoria which is extended when, in the middle of his session, Dr. Swanson suffers a fatal heart attack.
With his new and improved outlook on life Peter is better able to function and put his foot down at much of Initech’s unreasonable demands––which wouldn’t you know it, puts him in line for a promotion.
Rounding out the personable and playful cast are Jennifer Aniston, Diedrich Bader, Gary Cole, David Herman, Ajay Naidu, and Stephen Root, and the plot, more character driven than it is situational, goes off on some particularly silly scenarios, one of which referencing Superman III––the one with Richard Pryor––of all things.
If you’ve ever worked in IT or enjoy Judge’s wry and here, surprisingly restrained observances, Office Space is time well spent.
10. There’s Something About Mary (1998)
As with all of their comedy films, Bobby and Peter Farrelly are every bit as interested in breaking taboos as they are in laughing over breaking wind, and There’s Something About Mary is no exception. In fact, perhaps what this puerile and plucky rom com is best remembered for is a hair gel gag that involves Mary (Cameron Diaz) applying a glob of polymer to her coif that’s actually semen––talk about versatility!
There’s Something About Mary details the story of Ted Stroehmann (Ben Stiller), whose dream prom date with Mary Jensen (Diaz) doesn’t quite work out due to an embarrassing injury involving Ted’s frank and beans in her bathroom before their departure. Several years later an adult Ted hires inept private dick Pat Healy (Matt Dillon) to track down Mary so he can reconnect with her and perhaps rekindle those passions from long ago.
A weasel on all counts, Pat lies to Ted about Mary as he uncovers all he can about her to dupe her into dating him instead. Ted, rather than surrender having come so far, decides to reconnect with Mary all the same and soon has to weave through numerous obstacles and deceptions that both Pat and Mary’s curious friend Tucker (Lee Evans) have placed in the way in order to win her over.
Bonus points to the Farrelly’s for working in some fun musical interludes and cameo narration from Jonathan Richman as well as making sure The Foundations’ twee opus “Build Me Up Buttercup” is stuck in your head for days after viewing.
9. Dazed and Confused (1993)
While American auteur Richard Linklater had already started to carve a considerable name for himself and a cult following via his influential film from 1991, Slacker, it’s his coming-of-age comedy Dazed and Confused that found his most appreciative admirers, especially if, like me, you were a teenager at the time of its release.
Set on the last day of school in 1976 in Austin, Texas, Dazed and Confused is a multi-protagonist picture that features a wide-ranging and very impressive cast of young stars that were almost all virtual unknowns at the time.
Joey Lauren Adams, Ben Affleck, Rory Cochrane, Adam Goldberg, Cole Hauser, Milla Jovovich, Jason London, Parker Posey, Nicky Katt, and scenery chewing (and stealing) Matthew McConaughey are among the fresh faces as the graduating class of Lee High School haunt pool halls, parking lots and keg parties ready to usher in an exciting summer.
Pivoting on star football player Randall “Pink” Floyd (London) ill-advised promise to abstain from partying all summer long to focus on the championship game as well as the unsavory hazing practices that seniors instigate on incoming freshman, much of the draw of Dazed and Confused comes from familiarity and nostalgia of being young and chasing desire, with a little booze and marijuana indulgence tossed in for added vim.
To anyone who ever wanted to fit in, be cool, find young love, listen to meaningful music with friends, and enjoy being a kid one last time before adult responsibilities come crowding in, this film is for you.
8. The Castle (1997)
Aussie filmmaker Rob Sitch, who co-wrote The Castle with Santo Cilauro, Tom Gleisner and Jane Kennedy, captured the glorious eccentricity of the quirky and good-humored Kerrigan family, with warm and winning results. Living in a makeshift home, the titular “Castle” is located just a couple of yards from the bustling Tullamarine Airport in Melbourne, and the clan are unabashedly prideful and proud of their detailed, modest, and rather tartan dwelling.
The patriarch of the Kerrigan clan is Darryl (Michael Caton), and his hand is forced into action after a building inspector representing the airport comes along and condemns their home, planning to knock it down and allow for expansion of the runways.
With the help of Tiriel Mora’s hilarious hack attorney Dennis Denuto, the Kerrigan family will defend their lot and watching them appear as blue collar heroes and fiercely loyal subjects is part of what makes The Castle such an endearing and enduring comedic tour de force. A prized classic and certainly Sitch’s magnum opus.