For cinephiles, 1999 is considered a banner year akin to 1939 (Gone with the Wind, The Wizard of Oz, etc.), but truth be told, the entire decade was freaking awesome.
1990:

10. The Exorcist III, director: William Peter Blatty
9. Reversal of Fortune, director: Barbet Schroeder
8. The Comfort of Strangers, director: Paul Schrader
7. The Hunt for Red October, director: John McTiernan
6. The Grifters, director: Stephen Frears
5. Edward Scissorhands, director: Tim Burton
4. Total Recall, director: Paul Verhoeven
3. Slacker, director: Richard Linklater
2. Metropolitan, director: Whit Stillman
1. Goodfellas, director: Martin Scorsese
It’s easy to understand why Goodfellas’ Henry Hill is drawn to the gangsters in his neighborhood. In Martin Scorsese’s cinematic universe, a life of crime (as in organized crime) is a blast — provided you can stay alive. Ray Liotta and Lorraine Bracco give big, bombastic performances as Hill and his wife, Karen, but Joe Pesci’s trigger-happy mafiosi Tommy is on a different level. Pesci is consistently electrifying here, whether he’s doling out retribution for being teased about his shoe-shining past or making Michael Imperioli dance around by firing a pistol at his heels. Scorsese allows his audience vicarious thrills by immersing them in gangster life. Michael Ballhaus’ camerawork is flashy and fluid, particularly a justly celebrated Steadicam long take as Henry and Karen saunter through NYC’s storied Copacabana nightclub. Scorsese employs all his cinematic tricks here, from knockout montages to banger needle-drops, even an unforgettable cameo for his own gray-haired mana.
1991:

10. My Own Private Idaho, director: Gus Van Sant
9. Beauty and the Beast, director: Gary Trousdale & Kirk Wise
8. The Doors, director: Oliver Stone
7. Delicatessen, director: Jean-Pierre Jeunet & Marc Caro
6. Homicide, director: David Mamet
5. Terminator 2: Judgment Day, director: James Cameron
4. City of Hope, director: John Sayles
3. The Silence of the Lambs, Jonathan Demme
2. JFK, director: Oliver Stone
1. Barton Fink, director: Joel Coen
John Turturro’s Barton Fink is a humorless, pretentious and thoroughly solipsistic playwright (patterned after Clifford Odets) who has been summoned by 1941 Hollywood to write a wrestling picture for Wallace Beery. Sound like a sweet gig? But the self-satisfied scribe is suffering a major case of writer’s block, and there’s also the matter of … is he in Hell? Nightmarish, paranoid and viciously funny, Barton Fink provides a canvas for filmmakers Joel and Ethan Coen to lacerate the movie studio system, piety and self-congratulatory intellectualism. The brothers also pummel the shit out of the life of the mind. As always with the Coens, the picture is impeccably cast, with great turns by John Goodman, Michael Lerner, Judy Davis, and John Mahoney as a William Faulkner proxy.
1992:

10. The Player, director: Robert Altman
9. One False Move, director: Carl Franklin
8. Hard Boiled, director: John Woo
7. A River Runs Through It, director: Robert Redford
6. Twin Peaks: Fire Walk with Me, director: David Lynch
5. Howard’s End, director: James Ivory
4. Glengarry Glen Ross, director: James Foley
3. Reservoir Dogs, director: Quentin Tarantino
2. Husbands and Wives, director: Woody Allen
1. Unforgiven, director: Clint Eastwood
David Peoples’ screenplay had kicked around Hollywood for years before it ended up on the desk of Clint Eastwood. By then, thankfully, the original title, The Cut Whore Killings, had been replaced by the more austere Unforgiven. Eastwood is William Munny, a widower and single father who reverts to his old, cold-blooded ways to collect a bounty on two cowboys who knifed a prostitute. Clint the actor is very good, but Clint the director is superb, generous enough to allow ample room for excellent supporting performances from Gene Hackman (who won an Academy Award as a sadistic sheriff), Morgan Freeman, Richard Harris and Saul Rubinek. “If I was ever to do a last Western,” Clint told The Los Angeles Times, “this would be it because it kind of sums up how I feel. Maybe that’s why I didn’t do it right away. I was kind of savoring it as the last of that genre, maybe the last film of that type for me.” Certainly Hollywood’s last great western, it also earned Oscars that year for best picture and best director.
1993:

10. King of the Hill, director: Steven Soderbergh
9. Fearless, director: Peter Weir
8. The Fugitive, director: Andrew Davis
7. Jurassic Park, director: Steven Spielberg
6. Short Cuts, director: Robert Altman
5. Dazed and Confused, director: Richard Linklater
4. Carlito’s Way, director: Brian De Palma
3. Groundhog Day, director: Harold Ramis
2. Schindler’s List, director: Steven Spielberg
1. The Nightmare before Christmas, director: Henry Selick
Any of the top five films listed above could well be my favorite for 1992, but none can rival this masterpiece of stop-motion animation for sheer repeated-viewing staying power. I can see The Nightmare Before Christmas over and over; and, as a result of parenthood, I have done so. Producer Tim Burton and director Henry Selick spent three years making this darkly funny and inventive mashup of Halloween and Christmas, and their obsessive attention to detail is apparent in every frame. The phantasmagorical imagery is great fun, of course, but this also happens to be one of the last great movie musicals, thanks to music score maestro Danny Elfman, who also lends his singing voice to displaced protagonist Jack Skellington.
1994:

10. The Lion King, director: Roger Allers & Rob Minkoff
9. Bullets Over Broadway, director: Woody Allen
8. Three Colours: Red, director: Krzysztof Kieślowski
7. The Shawshank Redemption, director: Frank Darabont
6. Quiz Show, director: Robert Redford
5. Heavenly Creatures, director: Peter Jackson
4. The Hudsucker Proxy, director: Joel Coen
3. Crumb, director: Terry Zwigoff
2. Ed Wood, director: Tim Burton
1. Pulp Fiction, director: Quentin Tarantino
Quentin Tarantino’s followup to Reservoir Dogs reveals a director so in love with the movies — exploitation movies, specifically — it is virtually impossible not to get a contact high from his enthusiasm. The greatness of Pulp Fiction (and make no mistake, it’s a masterpiece) comes from “its marriage of original characters (essentially comic) with a series of vivid and half-fanciful events — and from the dialogue,” wrote Roger Ebert. “The dialogue is the foundation of everything else.” He was right, of course, about the stylized, pop culture-saturated dialogue courtesy Tarantino and Roger Avary. In the end, Pulp Fiction boasts a vibe aa cool as three little Fonzies, and for a multitude of reasons: its circular, nonlinear structure; the inspired performances; the dance at Jack Rabbit Slim’s, the gimp…
1995:

10. Clockers, director: Spike Lee
9. Sense and Sensibility, director: Ang Lee
8. Se7en, director: David Fincher
7. Before Sunrise, director: Richard Linklater
6. Apollo 13, director: Ron Howard
5. Casino, director: Martin Scorsese
4. To Die For, director: Gus Van Sant
3. Toy Story, director: John Lasseter
2. Heat, director: Michael Mann
1. 12 Monkeys, director: Terry Gilliam
A few years ago I saw Chris Marker’s La Jetée for the first time. Until then, I had no idea that Terry Gilliam’s sci-fi masterpiece was essentially a reimagining. But 12 Monkeys is much more than a remake. The screenwriting team of David and Janet Peoples create a tale that is rueful, funny, and endearingly twisted. Bruce Willis is an inmate sent from a dystopian future back in time to investigate 1995, when the advent of a virus would eventually decimate the planet (not surprisingly, 12 Monkeys was essential viewing during COVID lockdown). It’s a great concept to ignite lots of ideas about memory, time, and technology. Brad Pitt plays a terrifically unhinged trust fund baby, an early indication that he could do comedy. The ending is one of cinema’s great eureka moments.
1996:

10. La Promesse, director: Luc Dardenne & Jean-Pierre Dardenne
9. Secrets & Lies, director: Mike Leigh
8. The English Patient, director: Anthony Minghella
7. The People vs. Larry Flynt, director: Miloš Forman
6. Jerry Maguire, director: Cameron Crowe
5. When We Were Kings, director: Leon Gast
4. Flirting with Disaster, director: David O. Russell
3. Breaking the Waves, director: Lars von Trier
2. Lone Star, director: John Sayles
1. Fargo, director: Joel Coen
A comic thriller about greed, failure and quiet decency — in other words, a very American movie — Fargo might just be the perfect realization of Joel and Ethan Coen’s playfully misanthropic worldview. A criminal scheme by William H. Macy’s desperate car salesman spirals out of control, leading to kidnapping and murder, and eventually the attention of intrepid rural police chief Marge Gunderson (Frances McDormand). “From one moment to the next this film is gruesome,, bloody, and ‘Oh, no!’ as well as so funny you wish those starchy voices would stop talking for a second,” observed movie scholar David Thomson. The filmmaking is impeccable and, like most of the Coen brothers’ oeuvre, Fargo is endlessly quotable (“He was a little guy, kinda funny lookin’,” “And I guess that was your accomplice in the wood chipper”) There are excellent performances all around, but McDormand, who won the Oscar, is unquestionably the MVP here.
1997:

10. Men in Black, director: Barry Sonnenfeld
9. Lost Highway, director: David Lynch
8. The Ice Storm, director: Ang Lee
7. Open Your Eyes, director: Alejandro Amenábar
6. Titanic, director: James Cameron
5. Funny Games, director: Michael Haneke
4. The Game, director: David Fincher
3. L.A. Confidential, director: Curtis Hanson
2. Jackie Brown, director: Quentin Tarantino
1. Boogie Nights, director: Paul Thomas Anderson
Paul Thomas Anderson’s sophomore effort is ambitious, audacious and admirably outrageous. In other words, it’s just what you might expect from a brilliant young director’s sophomore effort. It’s all right there in the opening shot: a bravura Steadicam long take that introduces us to all the main characters. Mark Wahlberg was never better as the naturally gifted porn star Dirk Diggler (loosely based on the late John Holmes) in this dazzling, nostalgia-soaked paean to the adult film industry of the 1970s and early 80s. Dynamic filmmaking (think Scorsese meets Altman) and an excellent soundtrack are buoyed by a dream-team ensemble that includes Burt Reynolds (who never appreciated the greatness of what would be his final picture), John C. Reilly, Philip Seymour Hoffman, Julianne Moore, William H. Macy, Don Cheadle and Heather Graham.
1998:

10. Primary Colors, director: Mike Nichols
9. Run Lola Run, director: Tom Tykwer
8. Out of Sight, director: Steven Soderbergh
7. The Celebration, director: Thomas Vinterberg
6. There’s Something About Mary, director: Bobby Farrelly & Peter Farrelly
5. The Thin Red Line, director: Terrence Malick
4. Saving Private Ryan, director: Steven Spielberg
3. The Truman Show, director: Peter Weir
2. Happiness, director: Todd Solondz
1. The Big Lebowski, director: Joel Coen
As the bathrobe-clad, Venice Beach stoner who just wants his rug back, man, Jeff Bridges heads up a very, very game cast — including John Goodman, Steve Buscemi, John Turturro, Philip Seymour Hoffman, Julianne Moore, David Huddleston and Sam Elliott— in a comic confection that somehow interweaves the Iraq War, film noir, Westerns, drug culture, the art world and bowling. Oh, and there are wonderful needle drops throughout, including an unforgettable hallucinatory scene to the tune of First Edition’s psychedelic “I Just Dropped In (To See What Condition My Condition Was In).” Brothers Joel and Ethan Coen’s broad mashup befuddled audiences during its theatrical release, but it achieved cult masterpiece status in record time. Proof positive that, indeed, the dude abides.
1999:

10. The Virgin Suicides, director: Sofia Coppola
9. Dick, director: Andrew Fleming
8.. Office Space, director: Mike Judge
7. Election, director: Alexander Payne
6. The Sixth Sense, director: M. Night Shyamalan
5. The Limey, director: Steven Soderbergh
4. Toy Story 2, director: John Lasseter
3. Magnolia, director: Paul Thomas Anderson
2. Fight Club, director: David Fincher
1. Being John Malkovich, director: Spike Jonze
The high-concept that fuels Being John Malkovich — that a portal exists by which people can temporarily live as the titular actor for 15 minutes before being unceremoniously dumped along the New Jersey turnpike — is amusing enough. But what makes this fantastical comedy a masterpiece is how Spike Jonze and screenwriter Charlie Kaufman approach the material as utterly plausible. John Malkovich is a great sport lampooning his brand of celebrity. The love triangle of John Cusack, Cameron Diaz and Catherine Keener comprise the bruised heart and soul of this gloriously poignant and profound meditation on identity.