30 Great Films of 1999 That Are Worth Your Time

It must have been all that pre-millennial tension. For one reason or another, 1999 truly brought out the best in cinema and film makers across the world. It saw great films from material that you would least expect, solid filmmakers step up to become excellent ones and some of the greatest films of the Nineties all in one year.

1999 inspired works that were challenging, intelligent, thought provoking and, in some cases, absolutely exceptional.

Here is a list of thirty movies from that year, illustrating the wide cross section that 1999 had in regards to influence and inspiration to cinema across the world.


30. Two Hands (Gregor Jordan)

Two Hands

This one’s a little bit out of left field. “Two Hands” is an Australian black comedy/drama set in the crime underworld of Sydney. Heath Ledger plays a young man who wants to get into ‘the game’ that is the crime world. In a brilliant performance, Bryan Brown plays Pando, the underworld big key pin.

Although it features a supernatural sub-plot that doesn’t quite work, “Two Hands”, from debutante director Jordan, is a wonderfully written black comedy; sort of like what you would imagine an Antipodean take on “Lock, Stock & Two Smoking Barrels” would be like. If you’re looking for a film that does something of a different dance with the crime genre, then “Two Hands” is for you.


29. American Pie (Paul Wietz)


A late nineties spin on the classic staple of teen comedy, losing one’s virginity, this was a fresh and charming take on a genre that many thought to be dead. With some great writing and acting to it, “American Pie”, while occasionally straying into ‘shock for shock’s sake’ territory, is a film that has a great deal of heart and empathy to it. It struck something of a chord across the world, becoming a massive hit at the box office.

Again, like “The Matrix”, the franchise was cheapened by lesser sequels, especially the direct to DVD ones that didn’t feature any major cast members. However, the original still rates for being highly entertaining and charming.


28. 10 Things I Hate About You (Gil Yunger)


Following on from the massive success director Baz Luhrman had with his remarkable adaptation of “Romeo And Juliet” in 1996, this totally charming take on Shakespeare’s “The Taming Of The Shrew” was one of the more successful modern takes on The Bard.

Featuring heart and style to burn, “10 Things” had a bubbliness that was hard to ignore, managing to melt even the hardest of hearts. Thankfully taming down the more misogynist and negative elements of the original text, this film proved to be the launching pad for two very talented actors, Julia Stiles and the late Heath Ledger.


27. Office Space (Mike Judge)


An acidic comedy from Mike Judge, creator of MTV’S “Beavis And Butthead”, this takes a broad swipe at working life, with all its inconsistencies, frustration and ability to destroy the soul.

A standout in this underrated comedy is where three workers, sick of dealing with a malfunctioning photocopy machine, ‘abduct’ it, take it to a field and beat it with baseball bats! Who hasn’t wanted to do that at some time in their lives.

An accurate and very funny look at work and how it affects life, “Office Space” somehow didn’t fire at the box office upon release. Again, this is another film that found the audience it so rightly deserves in the home market.


26. Man On The Moon (Milos Forman)


Not the most prolific of directors, Czech expatriate Forman brings his sublime skills to the fore to create a highly entertaining biopic on cult American comedian Andy Kaufman. Wonderfully ed by Jim Carey, this enigmatic and enjoyable film lets us into the mysterious life and times of Kaufman, an avant-garde comedian that many didn’t ‘get’ when he was alive.

Also starring Courtney Love and one of Kaufman’s compatriots, Danny De Vito (Kaufman’s co-star in the TV show “Taxi”), this is biopic at its most unconventional, but no less entertaining for being so.


25. Romance (Catherine Breillat)


Uncompromising in the way that only a French director can be, Catherine Breillat’s “Romance” was the film that really introduced her to a greater audience.

Depicting a female school teacher experiencing highly charged and challenging sexual situations, this is not pornography, despite how frank its depiction of sex is.

This is a film that will confuse and provoke in a highly emotional manner. While a bleak and depressing film, it stands out for its intelligence and depth in the way it looks at sex and what it means to us as human beings.


24. eXistenZ (David Cronenberg)


At a point where he was well into his career, Canadian director David Cronenberg was showing no signs of fatigue in regards to his keen intellect in cinema. “eXistenZ”, following hot on the heels of his highly controversial adaptation of the J.G. Ballard novel “Crash”, was a strong illustration of Cronenberg as provocateur, always wanting to push limits and boundaries.

Starring Jude Law and Jennifer Jason Leigh, this look at the video game world covers the director’s obsessions that have run throughout all of his films, such as love, sex, death, reality and insanity.

Visually stylish and thematically compelling, “eXistenZ” is a film that will challenge and provoke in equal measure.


23. Boys Don’t Cry (Kimberly Pierce)


Based on an explosive true story, “Boys Don’t Cry” was a lacerating, powerful film about gender identity and being. Hilary Swank, in an Oscar winning performance, plays a woman who dresses as a man, confused about her identity and being. The ramifications that follow are swift and deadly.

Co-starring Chloe Sevigny and Peter Saasgaard, this was cinema at its most personal and impactful. It’s a shame that talented director Pierce has only made two films since this, her debut feature.


22. Go (Doug Liman)


Fresh of the success of “Swingers”, this was director Doug Liman’s sophomore effort. Featuring a circular narrative where three stories dovetail into one, “Go” beautifully captured that time in one’s life where, in their late teens and early twenties, they are young, full of energy, think they’re bulletproof and all the strange and crazy adventures they get into.

Featuring a bright and energetic visual style, “Go” is a film with energy to burn. It also has a great cast to it, featuring the likes of Timothy Olyphant, Sarah Polley, Scott Wolf and Katie Holmes. “Go”, like its title, is punchy, energetic and really captures beautifully the time when one jumps off from being a child/teenager to being an adult.


21. Ghost Dog: The Way Of The Samurai (Jim Jarmusch)

ghost dog

Jim Jarmusch is one of the most unique, highly idiosyncratic and individual directors working today. All of his films, from “Mystery Train” to his latest, “Only Lovers Left Alive”, have a truly different and personal sense of identity and being to them. His 1999 film, “Ghost Dog: The Way Of The Samurai”, is no different.

A slow, meditative crime drama, Forrest Whittaker stars as an African-American hit man who models his way of life on that of the Japanese Samurai. A thoughtful look at a man who lives by a code, “Ghost Dog” is a wonderfully left of centre take on the crime film. “Ghost Dog” is definitely recommended if, as a lover of cinema, you’re searching for something out of the ordinary.