Great Years of Cinema: 1999

Brad Pitt made his mark in the legendary Fight Club

Compiled by Eddie on 28/08/2020

1999 was a year unlike any other with the intrigue and anticipation that surrounded the dawn of the 2000’s ever present but in the midst of everything else that was occurring in that unforgettable year was a 12 month period of cinema that will live long in the echelons of incredible years for film fans.

With an eclectic array of films from an abundance of genres, that just so happened to be overflowing with long-standing comedies that arguably created the last truly great year for the big screen genre, 1999 had something for everyone with a mix of up-starts and icons delivering the goods.

In the list arranged below, just some of 1999’s most memorable films are mentioned, all that I am sure you would agree makes for a fairly unquestionable case for the year being one of the greats of cinema.

Happy reading and happy watching!


Tom Cruise delivered one of most unexpected and great turns against type in Magnolia


Director: Paul Thomas Anderson Cast: Tom Cruise, John C. Reilly

A multi-character but intimate epic, Magnolia remains one of director Paul Thomas Anderson’s finest creations that has heart, soul and humanity to spare. Features some amazing performances from its loaded cast with incredible turns from Tom Cruise and John C. Reilly in particular.

The Green Mile

Director: Frank Darabont Cast: Tom Hanks, Michael Clarke Duncan

While he will forever be known as the director that gave us The Shawkshank Redemption, Frank Darabont is also responsible for this other Stephen King prison based adaptation that is just as moving as his touchstone work. A highly memorable drama that gave us the great double billing of Tom Hanks and Michael Clarke Duncan as a bonus.

American Beauty

Director Sam Mendes created an all-time classic with his first feature American Beauty

Director: Sam Mendes Cast: Kevin Spacey, Wes Bentley

As far as cinematic debuts go they don’t get much better than Sam Mende’s Oscar winning classic American Beauty. Telling the story of Kevin Spacey’s middle-aged Lester Burnham going through some odd but somehow relatable everyday crisis situations, this visually arresting and narratively rich film is one of the finest of its kind from the 90’s.

The Insider

Director: Michael Mann Cast: Al Pacino, Russell Crowe

One of the lesser spoken about works of Michael Mann’s filmography, The Insider is a searing dramatic thriller based on real life events that teams up Russell Crowe and Al Pacino to great effect. Filled with tension and well-rounded character development, The Insider is a fine piece of cinema in almost every department.

Man on the Moon

Director: Milos Foreman Cast: Jim Carrey

In one of the performances of his career, Jim Carrey wonderfully brings larger than life comic Andy Kaufman to the big screen in esteemed director Milos Foreman’s biography. Underappreciated upon initial release, Man on the Moon is now regarded as the classic it deserves to be seen as.

Honorable Mentions – The Straight Story, Any Given Sunday


It’s not high-class cinema but The Mummy is cinema at its most enjoyable and entertaining

The Mummy

Director: Stephen Sommers Cast: Brendan Fraser, Rachel Weisz

Not high-class cinema, there’s something truly special about the fun The Mummy has in bringing its world to life on the big screen, heralded in by a collection of strong performances and Brendan Fraser at his most charismatic. A truly enjoyable guilty pleasure, The Mummy is the type of big budget offering we don’t get a lot of these days.

Fight Club

Director: David Fincher Cast: Edward Norton, Brad Pitt

David Fincher’s most widely regarded classic, Fight Club may’ve been a box office disappointment upon release but it didn’t take long to be seen as one of the greatest pieces of film-making ever committed to the big screen. With two on song leads in the form of Edward Norton and Brad Pitt and a story that still resonates today, Fight Club is king of its class.

Deep Blue Sea

Director: Renny Harlin Cast: Thomas Jane, LL Cool J

An absolute riot of popcorn film-making, Renny Harlin’s Jaws on steroids remains the type of endlessly re-watchable piece of trashy cinema that is 100% so bad its good. Embracing it’s over the top nature and giving us an endless procession of memorable set pieces, Deep Blue Sea remains one of the best shark based movies of all time.

Honorable Mentions – Two Hands, Three Kings


Is there a cooler movie trio? The Matrix was and still is a cultural sensation

The Matrix

Directors: The Wachowski’s Cast: Keanu Reeves, Laurence Fishburne

Creating a whole new genre and taking the world by storm with its mix of insane special effects, action and endlessly cool performances, The Matrix is a touchstone piece of science fiction storytelling that remains a cultural phenomenon to this day.

The Blair Witch Project

Director: Daniel Myrick & Eduardo Sánchez Cast: Heather Donahue, Joshua Leonard

A film that still stands as one of the most successful financial ventures of all-time, the birth of the found footage horror film began with The Blair Witch, a film that changed the horror genre and how films are marketed forever. It may not be as scary today as it was upon release but The Blair Witch Project deserves to be remembered as a genuine game changer.

The Sixth Sense

Director: M. Night Shyamaylan Cast: Bruce Willis, Haley Joel Osment

Never able to fully capture the greatness he found with his debut here, director M. Night Shyamaylan took the world by storm when he unleashed The Sixth Sense on the world. Creating a star child performance from Hayley Joel Osment and giving us one of Bruce Willis’s last good performances, this twisting horror/thriller is a classic of the genre.


Director: Antonia Bird Cast: Guy Pearce, Robert Carlyle

A film that remains an underseen gem (Jordan wrote a great review of the film many moons ago here on the blog), Ravenous is a dastardly fun horror ride with some great performances to boot. Full of atmosphere and intrigue, Antonia Bird’s classic is a film you need to track down ASAP.


Office Space has become an all time cult classic in the years since its initial release

Office Space

Director: Mike Judge Cast: Ron Livingston, Jennifer Aniston

Most well-known for birthing Bevis and Butthead and King of the Hill into the world, creator Mike Judge nailed his comedic venture Office Space so much so that after 20 years on from release the stature of this smartly observed skewering of office life and working for the man is only growing in reputation.

Being John Malkovich

Director: Spike Jonze Cast: John Malkovich, Cameron Diaz

One of the most bonkers and original offerings of the 90’s, Spike Jonze’s critical hit Being John Malkovich may not suit all tastes but it’s an undeniably effective piece of smartly tuned cinema that remains one of the director’s greatest pieces of work.

Galaxy Quest

Director: Dean Parisot Cast: Tim Allen, Allan Rickman

Ahead of its time in its observations of pop culture and toxic fandom, Galaxy Quest unites a great cast for a seriously fun ride through the universe. It may not make a lot of sense and some of its jokes have failed to stand the test of time but overall this cult classic remains an incredibly fun comedic ride.

Mystery Men

Mystery Men featured an all-star cast as a crazy bunch of colorful characters

Director: Kinka Usher Cast: Ben Stiller, Hank Azaria

Featuring a group of superheroes very different to what comes out of the Marvel wheelhouse, Mystery Men was a box-office dud when it first appeared but remains a cult classic to this day thanks to its high laugh ratio and loaded cast.

American Pie

Directors: Paul and Chris Weitz Cast: Jason Biggs, Sean William Scott

One of the defining teenage comedies of the 90’s, American Pie made stars of its then up and coming cast and changed the teenage genre of comedy films forever. A massive hit that spawned a number of wide ranging sequels and spin-offs, this is raunchy offering that works.

10 Things I Hate About You

Director: Gil Junger Cast: Julia Stiles, Heath Ledger

With two insanely charismatic leads, 10 Things I Hate About You took the world by storm and made a star of Heath Ledger in the process. It may be daft and over the top in many areas, but there’s a charm and magic found in Gil Junger’s film that remains ever present even unto this day.

Honorable Mentions – Election, Analyze This, Bowfinger, Dogma


The Iron Giant is one of the last great hand-drawn classics

The Iron Giant

Director: Brad Bird Cast: Vin Diesel, Jennifer Aniston

Brad Bird will always be remembered for helping bring The Simpson’s to life and directing Pixar classic’s Ratatouille and The Incredibles but one could argue his greatest achievement as a creator remains the underappreciated The Iron Giant. A hand animated gem that is full of heart and soul, this is the special type of film that is meaningful to those of all ages.

Toy Story 2

Directors: John Lasseter & Ash Brannon Cast: Tim Allen, Tom Hanks

The first Toy Story was a beloved piece of cinema but proving to everyone that is was no fluke, Toy Story 2 upped the game with a highly moving and insanely fun second outing. Bringing back everyone’s favorite toys and adding a whole bunch of memorable new ones to the equation, this brilliantly animated and written CGI offering is an endlessly charming affair.

What are some of your favorite films of 1999? Are there any offerings I have overlooked? Let me know in the comments below!

Other great years are cinema are – 







22 responses to “Great Years of Cinema: 1999

  1. So many good films! By sheer coincidence I recently rewatched and reviewed the Matrix over on my own blog. It’s a movie that’s still so incredibly good after all these years😊 Nice to see The Insider mentioned here as well. In my opinion such an underrated movie. Really one of Crowe’s best roles of his career.

    • I think I will go through the Matrix films closer to the new one’s release mate, its a been a few years!

      Great to hear your a fan of The Insider, a very underrated film.

  2. Great year.

    My top two are cheats, as they premiered at film festivals that year. So, if you accept Denis’ Beau Travail – one of my all time favourite films – then it’s that for me. Also, if you include Miike’s Audition, that’s a strong number 2.

    In terms of cinematic release, my favourite would probably be Almodóvar’s masterpiece, All About My Mother.

    I’d also include David Lynch’s strangest film, The Straight Story – strangest because it’s a conventional, Disney produced, family friendly drama.

    Election is also up there for me (though with recent allegations against Payne tarnish it right now).

    I’m also a lover of Cronenberg’s eXistenZ, though it’s not top tier Cronenberg.

    I’d also throw in a token reference to Eyes Wide Shut which, though I’m not a big fan, is one of the year’s most important films – and is a fascinating movie.

  3. Once upon a time, when Hollywood’s critically and popularly acclaimed films overlapped more often than not (and the panned ones became cult hits or guilty pleasures).

    I’d add Blast From the Past starring Brendan Fraser and Alicia Silverstone — it’s ridiculously funny.

    It’s not American, but Lock, Stock, and Two Smoking Barrels should get an honorable mention as it introduced Guy Ritichie to more English language cinemas.

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