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Ranking the films of 1999, pt. 2

| Thursday, October 3, 2019

Cristina Interiano | The Observer

Yesterday, I counted down the 20-11 spots on my list of the best films from 20 years ago. Today, I’m joined by a group of ornery Colorado children, a particularly talented impostor and John Malkovich to list the 10 best movies of 1999.


  1. “South Park: Bigger, Longer & Uncut” (directed by Trey Parker and Matt Stone)

Don’t laugh. All of the worst tendencies of the long-running animated series are sanded down for its feature film adaptation, with Cartman and company taking a stand against censorship in an uproariously puerile farce that just may be the best film musical of the last 20 years.

  1. “Dogma” (directed by Kevin Smith)

Smith is one of the most purely talented comic writers to work in any medium with a dedication to rhetoric more akin to George Bernard Shaw than any screenwriter. His target is the Catholic Church, but instead of skewering organized religion, Smith uses his slyly heartfelt tale of two exiled angels and a 13th apostle to expertly interrogate how Catholicism can help and hinder in equal measure.

  1. “Being John Malkovich” (directed by Spike Jonze)

Along with screenwriter Charlie Kaufman, Jonze crafts a wildly inventive tale of a puppeteer and his wife who discover a portal into the head of actor John Malkovich — playing himself in a nifty bit of self-mythologizing.

  1. “The Sixth Sense” (directed by M. Night Shyamalan)

Even if the film’s final twist has been spoiled by 20 years of discourse, Haley Joel Osment’s delivery of “I see dead people” still has the power to stop viewers in their tracks. That Shyamalan had to be convinced to change the iconic line from his original “I observe deceased individuals” only speaks to the alchemical nature of his near-perfect first feature.

  1. “Todo Sobre Mi Madre” (directed by Pedro Almodovar)

In a career built on empathetic portrayals of life’s outcasts, Almodovar hits his peak with this story of pregnant nuns, transgender sex workers and grieving mothers. With a title that alludes to “All About Eve” and a plot that nods to Tennessee Williams, “Todo Sobre Mi Madre” is a heartbreaking portrayal of the families we make for ourselves.

  1. “The Blair Witch Project” (directed by Daniel Myrick and Eduardo Sanchez)

Full disclosure: Any one of the top five films here could have been number one on this list. Of those five, certainly none are more influential than “Blair Witch,” a genuinely terrifying film that pioneered found-footage horror and guerrilla internet marketing in equal measure. It is a movie even non-horror fans need to watch; that being said, maybe turn a few lights on first.

  1. “Office Space” (directed by Mike Judge)

Easily the most quotable movie on this list, Judge’s comedic triumph turns the impending Y2K scare into just another day at the office. Armed with a killer cast and an equally hilarious soundtrack (shout-out to the Geto Boys’ immortal “Damn It Feels Good To Be A Gangsta”), “Office Space” is a beautiful ode to the allure of doing nothing — and liking it.

  1. “The Talented Mr. Ripley” (directed by Anthony Minghella)

Fresh off the painfully overwrought “The English Patient,” Minghella’s adaptation of Patricia Highsmith’s novel feels positively breezy despite its two-hour-plus runtime. A fashionable, chilling thriller, “Ripley” is bolstered by its trio of lead performers: Matt Damon, Gweneth Paltrow and a never-better-looking Jude Law give life to Highsmith’s characters as Minghella translates her lavish prose to the big screen.

  1. “Three Kings” (directed by David O. Russell)

“Are we shooting?” With those three words, Mark Wahlberg’s Troy Barlow plunges us into Russell’s kinetic war satire, where the Gulf War is a playground for bored American soldiers until they’re forced to act against their government’s wishes. The best scene of any 1999 movie is George Clooney’s exasperated definition of the Kuwaiti bullion at the center of the plot — “No, not the little cubes you use to make soup.”

  1. “Election” (directed by Alexander Payne)

When it was released, Payne’s second feature was a slight commercial flop and equally modest critical success. The subsequent years, however, have revealed “Election” as the masterpiece it truly is. Never has the Midwest been more accurately portrayed on screen; never has the sexism and egocentrism of politics been better crystallized into a wickedly entertaining package, all served up like one of Tracy Flick’s signature cupcakes.

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