1999 is generally considered to be one of the greatest years in cinema, and I couldn’t agree more. After recently stumbling upon another priceless gem from that year (see #8), I decided to rank the Top 9 Films of 1999, followed by a bonus list of 19 runners-up. Believe me, there’s plenty more where that came from.

9. Election

Every time election season comes around, I’m reminded of Alexander Payne’s razor-sharp satire that managed to explore the modern political scene through the guise of a high school comedy. Reese Witherspoon is unforgettable as the monstrously ambitious class president hopeful, while Matthew Broderick gives the performance of his career as the impotent, chronically unlucky civics teacher–the sort of sad sack that Ferris Bueller could outwit without breaking a sweat. As great as the showdowns are between Witherspoon and Broderick, the scene I hold dearest to my heart is the assembly where the unlikeliest of candidates–an unpopular, budding lesbian (Jessica Campbell)–delivers a truly crowd-pleasing speech…

8. Rosetta

The Dardenne Brothers are masters of suspense on par with Hitchcock, yet their films rely more on documentary realism than impressionistic angles. 17-year-old Émilie Dequenne won the Best Actress award at Cannes for her galvanizing performance as the titular heroine desperately seeking employment. The camera creates tension simply by focusing on Rosetta’s expressive face as nearby threats remain concealed offscreen. The film, which also garnered the prestigious Palme d’Or, recently received an excellent Blu-ray release courtesy of Criterion. Click here to read my review for HollywoodChicago.com.

7. The Insider

Michael Mann was at his very best when he helmed this explosive drama about a Big Tobacco scandal that threatened to destroy the life of a lone whistleblower (played by an uncommonly understated Russell Crowe). The talent-packed cast is led by Al Pacino and Christopher Plummer, though my favorite performance is by the great character actor Bruce McGill, who literally hammers a smug foe into the ground with the ferocity of his words. Just look at him in this scene. “Wipe That Smirk Off Your Face!” should be every bit as immortal a line as “You talkin’ to me?”

6. The Sixth Sense

Forget the twist ending or the media hype that surrounded it or the fact that writer/director M. Night Shyamalan would never come close to equaling it again. Curious how his career crash-landed at the precise moment his ego skyrocketed. It’s a damn shame, since his one truly beloved hit deserves every inch of the praise that was heaped upon it. This isn’t an extended “Twilight Zone” episode that relies purely on gimmickry. It is a deeply touching drama about the pain of alienation and the inability to connect. The performances by Haley Joel Osment and Toni Collette are among the most moving I’ve ever seen. Their big scene in the parked car (sampled below) is one of the few movie moments that never fails to make me cry. If you are one of the few humans on earth who hasn’t seen the film yet, please skip the clip. You’ll thank me later.

5. Boys Don’t Cry

Kimberly Peirce’s dramatization of Brandon Teena’s extraordinary yet ill-fated life is so brutally wrenching that audiences may not care to sit through it twice. Yet it’s a picture that simply cannot (and should not) be missed. Hilary Swank’s Oscar-winning embodiment of Teena is matched every step of the way by Chloë Sevigny’s devastating portrayal of the wayward girl who falls for “him.” Peirce never loses sight of the central love story while refusing to make Teena a mere social symbol. This is perhaps the most captivating variation on the “Romeo and Juliet” tale in cinema history.

4. Being John Malkovich

The mad genius of screenwriter Charlie Kaufman erupted onto the screen in full force courtesy of the adventurous filmmaker Spike Jonze and a game cast. John Cusack has a field day as a struggling street performer who stumbles upon a portal into the mind of self-obsessed actor John Malkovich (played by–who else?–Malkovich). This darkly funny look at puppeteering–in all of its most perverse forms–is chockfull of classic scenes: the office located on Floor 7 1/2, the chase scene through Malkovich’s subconscious and, of course, Malkovich’s personal trip through his own brain portal. It’s enough to make your own brain burst with giddiness. “Malkovich, Malkovich?”

3. The Blair Witch Project

Unfairly dismissed by modern viewers as a glorified YouTube video, this groundbreaking indie horror sensation changed the art form for better and worse. It’s far more terrifying than any of its imitators, including the original “Paranormal Activity.” Directors Daniel Myrick and Eduardo Sánchez literally stranded their actors in the woods and proceeded to devise increasingly fiendish methods of freaking them out. Heather Donahue, Michael C. Williams and Joshua Leonard are completely convincing as the young trio of would-be documentarians, and Leonard’s improvised line about Heather’s obsessive need to keep filming still stands as the best explanation of its kind: “It’s not the same on film is it? I mean, you know it’s real, but it’s like looking through the lens gives you some sort of protection from what’s on the other side.”

2. The Straight Story

In between the elusive weirdness of “Lost Highway” and the blistering brilliance of “Mulholland Dr.,” David Lynch made one of the greatest films of his career–for Walt Disney Pictures. He regards the fact-based story of Alvin Straight–an elderly man who traveled on a riding mower for days upon days in order to visit his ailing brother–with a clear-eyed simplicity that is heartbreakingly beautiful. This is one of the most poignant films about old age ever made. Richard Farnsworth’s lead performance is beyond phenomenal, as is the score by Angelo Badalamenti. Here’s my favorite section of the music, entitled “Laurens Walking” (please disregard the dubbed dialogue)…

1. Magnolia

Is there any filmmaker in America as excitingly unpredictable as Paul Thomas Anderson and has there been any American film in the last decade as wildly audacious and breathtakingly alive as Anderson’s third directorial effort, the operatic ensemble drama, “Magnolia”? Fusing the stylistic urgency of Scorsese with the narrative impulses of Altman, this gloriously exuberant, profoundly sad look at a smorgasbord of LA lonely hearts has the playfulness of a magic act and the emotional stakes of a Shakespearean tragedy. When the actors spontaneously break into an Aimee Mann song, it feels absolutely right. And what actors they are. This is the film that introduced me to Philip Seymour Hoffman, Julianne Moore, John C. Reilly, William H. Macy, Phillip Baker Hall and Melora Walters. Needless to say, I’ve loved them ever since.

19 Runners-Up (in alphabetical order)

All About My Mother by Pedro Almodóvar

American Beauty by Sam Mendes

Audition by Takashi Miike

Bringing Out the Dead by Martin Scorsese

Eyes Wide Shut by Stanley Kubrick

Fight Club by David Fincher

The Iron Giant by Brad Bird

The Limey by Steven Soderbergh

The Matrix by Andy and Lana Wachowski

Mr. Death: The Rise and Fall of Fred A. Leuchter, Jr. by Errol Morris

Princess Mononoke by Hayao Miyazaki

Ratcatcher by Lynne Ramsay

Run Lola Run by Tom Tykwer

Sweet and Lowdown by Woody Allen

Three Kings by David O. Russell

Topsy-Turvy by Mike Leigh

Toy Story 2 by John Lasseter, Ash Brannon and Lee Unkrich

The Virgin Suicides by Sofia Coppola

The War Zone by Tim Roth