By: James A. Barnes

1999 produced some of the most iconic films ever made and will go down as one of the greatest years for Cinema history.

“The Matrix” was a once-in-a-lifetime type of film that changed how Hollywood made movies forever. I love its themes surrounding what makes humans human and shines a light on becoming reliant on technology and how it can be both an escape and a prison. The film is also filled with some of the most gripping fight sequences ever put to screen, and Keanu Reeves, Carrie-Ann Moss, and Laurence Fishburne were born to play their characters. 

“Fight Club” tackled the dangers of consumerism, classism, perfectionism, and the need to fit into society in order to feel “normal”. The film also features one of my favorite performances from both Brad Pitt and Edward Norton and has one of the best twists in movie history. 

Here are my picks for the 25 best films of 1999.

South Park: Bigger, Longer & Uncut

ROTTEN TOMATOES: 80% CRITIC RATING | 88% AUDIENCE RATING

In this cinematic adaptation of the beloved animated series, a group of South Park's third graders manages to slip into an R-rated movie featuring the outrageously crude Canadian duo, Terrance and Phillip. As a result, their vocabulary expands in shocking ways, causing uproar among parents and teachers. The film's censorship sparks a nationwide conflict between the United States and Canada, leading to the imprisonment of Terrance and Phillip, and leaving only the kids as their last hope for salvation.

Directed by: Trey Parker

Sleepy Hollow

ROTTEN TOMATOES: 70% CRITIC RATING | 80% AUDIENCE RATING

Set in 1799, "Sleepy Hollow" draws inspiration from Washington Irving's timeless tale, "The Legend of Sleepy Hollow." Embracing the enchanting atmosphere depicted in Irving's narrative, this film weaves together elements of horror, fantasy, and romance. With a captivating ensemble of characters delving into the realm of the supernatural, "Sleepy Hollow" offers a mesmerizing cinematic experience.

Directed by: Tim Burton

The Hurricane

ROTTEN TOMATOES: 83% CRITIC RATING | 87% AUDIENCE RATING

Denzel Washington stars as Rubin "Hurricane" Carter, a determined individual whose aspirations of claiming the middleweight boxing championship were shattered when he found himself implicated in the tragic murders of three individuals at a New Jersey bar. Unjustly accused, Carter and his companion John Artis were sentenced to three lifelong prison terms. This emotionally charged film chronicles their harrowing journey, highlighting the quest for justice and the resilience of the human spirit.

Directed by: Norman Jewison

Election

ROTTEN TOMATOES: 92% CRITIC RATING | 79% AUDIENCE RATING

Matthew Broderick portrays Jim McAllister, a beloved government teacher at a high school. Jim becomes increasingly aware of the unscrupulous methods employed by Tracy Flick, a highly accomplished student portrayed by Reese Witherspoon, to achieve her goals. When Tracy decides to run for the position of school president, Jim believes that her influence on the student body would be detrimental. In an effort to counter Tracy's campaign, Jim convinces Paul, a popular but not particularly bright student-athlete, to challenge her. However, when Tracy discovers Jim's secret involvement in the race, a bitter and intense rivalry ensues.

Directed by: Alexander Payne

The Boondock Saints

ROTTEN TOMATOES: 27% CRITIC RATING | 91% AUDIENCE RATING

Driven by their faith and a profound desire to eradicate the rampant crime plaguing the streets of Boston, Conner (Sean Patrick Flanery) and Murphy (Norman Reedus), twin brothers of Irish Catholic descent, embark on a mission to purge their hometown of wickedness. Determined to administer their unique form of vigilantism, they become relentless forces against evil, striving to restore peace and justice to their community.

Directed by: Troy Duffy

Dogma

ROTTEN TOMATOES: 67% CRITIC RATING | 85% AUDIENCE RATING

After being expelled from Heaven and condemned to a life of exile in Wisconsin, two fallen angels, Bartleby (Ben Affleck) and Loki (Matt Damon), discover a crucial opportunity for redemption. A church in Red Bank, New Jersey, marking its centennial anniversary, holds the power to absolve their sins and grant them reentry into Heaven upon death. Unbeknownst to them, however, their decision to enter the church will unravel the fabric of existence, defying the divine order and jeopardizing the very foundations of reality.

Directed by: Kevin Smith

Girl, Interrupted

ROTTEN TOMATOES: 53% CRITIC RATING | 84% AUDIENCE RATING

Taking place during the transformative era of the late 1960s, "Girl, Interrupted" delves into the raw and authentic tale of Susanna Kaysen (Winona Ryder). Plunged into a renowned mental institution for troubled young women, Susanna is faced with a pivotal decision. She must navigate between two distinct worlds—the captivating and perilous realm of individuals who belong within the institution, embodied by the seductive and unpredictable Lisa (Angelina Jolie), and the challenging yet essential reality of the outside world.

Directed by: James Mangold

10 Things I Hate About You

ROTTEN TOMATOES: 71% CRITIC RATING | 69% AUDIENCE RATING

Kat Stratford (Julia Stiles) possesses both beauty and intelligence, but her sharp tongue and abrasive demeanor make it difficult for her to connect with her peers, especially boys. The situation becomes complicated when her younger sister, Bianca (Larisa Oleynik), is forbidden from dating until Kat finds a boyfriend. As a result, a series of events is set in motion to orchestrate a potential romance for the reluctant Kat. In this process, she encounters the charming and enigmatic Patrick Verona (Heath Ledger), a new arrival to their town. The question arises: Will Kat allow herself to let her guard down and succumb to the irresistible allure of Patrick?

Directed by: Gil Junger

The Green Mile

ROTTEN TOMATOES: 79% CRITIC RATING | 94% AUDIENCE RATING

Paul Edgecomb (Tom Hanks) has spent his time as a prison guard accompanying various convicts down the mile. However, none of them compare to the enigmatic John Coffey (Michael Clarke Duncan), an imposing African-American man accused of a brutal double murder of young sisters. Despite Coffey's intimidating physical stature, his demeanor is far from menacing. Behind his innocent and childlike nature, coupled with an irrational fear of darkness, lies a seemingly extraordinary and otherworldly ability. As Paul forms a bond with Coffey, he starts to question the truth behind the heinous crimes attributed to him, wondering if Coffey is truly guilty or if there is more to the story.

Directed by: Frank Darabont

Three Kings

ROTTEN TOMATOES: 94% CRITIC RATING | 77% AUDIENCE RATING

Set in the aftermath of the Gulf War, a group of four American soldiers seizes the opportunity to steal a valuable hoard of hidden gold belonging to Saddam Hussein. Under the guidance of the jaded Sergeant Major Archie Gates (George Clooney), three of the soldiers find themselves rescued by local rebels, while Sergeant Troy Barlow (Mark Wahlberg) is taken captive and subjected to brutal interrogation by Iraqi intelligence. Recognizing their common enemy, the Iraqi rebels implore the remaining American trio to join forces and combat the imminent threat posed by Hussein's Elite Guard. In exchange for their assistance in rescuing Troy, the soldiers agree to lend their fighting prowess to the rebels' cause.

Directed by: David O. Russell

The Insider

ROTTEN TOMATOES: 96% CRITIC RATING | 90% AUDIENCE RATING

Intrigued by the guarded behavior of former "Big Tobacco" executive Jeffrey Wigand (Russell Crowe), seasoned TV producer Lowell Bergman (Al Pacino) becomes convinced that there is a compelling story behind Wigand's reticence. Determined to uncover the truth, Bergman manages to persuade Wigand to reveal his insider knowledge of the tobacco industry's hidden secrets. However, their path to exposing the truth is obstructed by legal battles and powerful corporate forces. Meanwhile, Wigand grapples with the challenges of protecting his family and personal life in the face of lawsuits and ominous threats.

Directed by: Michael Mahn

The Talented Mr. Ripley

ROTTEN TOMATOES: 85% CRITIC RATING | 80% AUDIENCE RATING

In the radiant late 1950s of Italy, where azure waters and picturesque landscapes abound, the young and carefree yearn for la dolce vita. Among them is Tom Ripley (Matt Damon), who becomes enamored with the captivating lifestyle led by the charismatic Dickie Greenleaf (Jude Law). When Dickie's father enlists Tom to bring his wayward son back to America, neither Dickie nor his alluring expatriate girlfriend, Marge Sherwood (Gwyneth Paltrow), suspect the perilous lengths to which Ripley will go in order to claim their idyllic existence as his own.

Directed by: Anthony Mingella

Magnolia

ROTTEN TOMATOES: % CRITIC RATING | % AUDIENCE RATING

Amidst the bustling San Fernando Valley, an assortment of lives converge on a serendipitous day. A father nearing the end of his life, a youthful wife, a devoted male caretaker, a renowned but elusive son, an enamored police officer, a prodigious young genius, a former child prodigy, a charismatic host of a game show, and a distant daughter find themselves entangled in a myriad of captivating narratives. While their individual journeys unfold, these diverse characters collectively contribute to a spellbinding tapestry of interconnected plots, forming a single, extraordinary tale.

Directed by: Paul Thomas Anderson

The Blair Witch Project

ROTTEN TOMATOES: 86% CRITIC RATING | 56% AUDIENCE RATING

Unearthed video footage chronicles the harrowing journey of three aspiring film students (Heather Donahue, Joshua Leonard, and Michael C. Williams) who embark on a quest to capture the haunting legend of the Blair Witch, a notorious local killer. Venturing into a small town, they conduct interviews and gather evidence to authenticate the chilling tale. However, their project takes a terrifying twist as they lose their bearings in the dense woods and are plagued by bone-chilling sounds that unsettle their very souls. In this suspenseful tale, the students' pursuit of truth transforms into a desperate battle for survival.

Directed by: Eduardo Sánchez and Daniel Myrick

Eyes Wide Shut

ROTTEN TOMATOES: 76% CRITIC RATING | 74% AUDIENCE RATING

When Dr. Bill Hartford (Tom Cruise) learns of his wife Alice's (Nicole Kidman) admission about her secret desires for another man, he becomes consumed by his own fixation on a sexual encounter. In his quest, he stumbles upon a clandestine society that indulges in unconventional desires. Tempted by curiosity, Bill decides to attend one of their enigmatic gatherings, only to find himself swiftly overwhelmed by the mysterious and perilous depths he has ventured into. In this gripping tale, Bill's pursuit of sexual exploration takes him on a journey where he must confront his own limits and grapple with the consequences of his choices.

Directed by: Stanley Kubrick

Galaxy Quest

ROTTEN TOMATOES: 90% CRITIC RATING | 79% AUDIENCE RATING

The former stars of a popular 1970s science fiction television series, whose lives now revolve around reruns and sci-fi conventions, find themselves unexpectedly transported onto an extraterrestrial spacecraft. The alien beings, perceiving the cast's fictional exploits as genuine historical events, seek their assistance in liberating their solar system from an oppressive regime. Tasked with fulfilling a heroic destiny beyond the realm of fiction, the ailing celebrities must rally together and use their fading fame to aid the alien species in their fight for freedom.

Directed by: Dean Parisot

Being John Malkovich

ROTTEN TOMATOES: 94% CRITIC RATING | 87% AUDIENCE RATING

In this beloved and offbeat comedy that has gained a devoted following, Craig Schwartz (John Cusack), an unemployed puppeteer in New York City, reluctantly accepts a temporary job as a filing clerk for the eccentric Dr. Lester (Orson Bean). Amidst his mundane tasks, Craig stumbles upon a mysterious portal that grants access to the mind of the renowned actor John Malkovich. As he shares this extraordinary discovery with his alluring co-worker Maxine (Catherine Keener), they embark on a peculiar business venture and navigate an unconventional relationship, further complicated by the involvement of Craig's restless wife, Lotte (Cameron Diaz).

Directed by: Spike Jonze

Man on the Moon

ROTTEN TOMATOES: 64% CRITIC RATING | 79% AUDIENCE RATING

In this captivating portrayal, Jim Carrey takes on the role of the legendary Andy Kaufman, a renowned and enigmatic performer known for his unparalleled innovation. Kaufman's ability to captivate audiences through his eccentric and unpredictable acts made him a true master of his craft. From generating uproarious laughter to provoking absolute silence, evoking tears or inciting chaos, Kaufman's performances were a rollercoaster of emotions. Whether inviting the audience to share in simple pleasures like milk and cookies or challenging societal norms with inter-gender wrestling matches, his boundary-pushing acts blurred the line between reality and illusion, leaving even his closest confidants uncertain of where truth truly resided.

Directed by: Miloš Forman

The Mummy

ROTTEN TOMATOES: 60% CRITIC RATING | 75% AUDIENCE RATING

In the year 1925, amidst an archaeological excavation within the ancient city of Hamunaptra, an American soldier serving in the French Foreign Legion unwittingly awakens a dormant mummy, stirring an ancient curse. This awakened entity, whose existence spans over three millennia, embarks on a destructive rampage while relentlessly seeking the reincarnation of his lost love. As chaos unfolds, the fate of all involved hangs in the balance within this enthralling tale of ancient forces unleashed.

Directed by: Stephen Sommers

The Iron Giant

ROTTEN TOMATOES: 96% CRITIC RATING | 90% AUDIENCE RATING

In this animated retelling of Ted Hughes' Cold War allegory, a colossal extraterrestrial robot (voiced by Vin Diesel) descends upon the quaint town of Rockwell, Maine, during the year 1957. While exploring his surroundings, the curious machine captures the attention of a young local boy named Hogarth, leading to an improbable bond between the two. However, as a paranoid government agent named Kent Mansley sets out to annihilate the robot, Hogarth and his unconventional friend, beatnik Dean McCoppin (voiced by Harry Connick Jr.), embark on a mission to protect the misunderstood mechanical being from impending destruction.

Directed by: Brad Bird

Toy Story 2

ROTTEN TOMATOES: 100% CRITIC RATING | 87% AUDIENCE RATING

When Woody (Tom Hanks) is unexpectedly snatched from his home by the unscrupulous toy dealer Al McWhiggin (Wayne Knight), Buzz Lightyear (Tim Allen) and their loyal companions embark on a daring mission to rescue their beloved friend. However, upon reuniting with his long-lost comrades, including Jessie the spirited yodeling cowgirl (Joan Cusack), his trusty horse Bullseye, and the cunning Stinky Pete the Prospector (Kelsey Grammer), Woody uncovers a startling revelation. Realizing his worth as a cherished collectible from a bygone television series called "Woody's Roundup," he becomes torn between his newfound identity and his loyalty to his cherished companions.

Directed by: John Lasseter

The Sixth Sense

ROTTEN TOMATOES: 86% CRITIC RATING | 90% AUDIENCE RATING

In this gripping tale, young Cole Sear (Haley Joel Osment) finds himself tormented by a haunting secret: he can see and communicate with restless spirits. Plagued by the unsettling presence of these unresolved apparitions, Cole harbors his fears in silence, except for confiding in child psychologist Dr. Malcolm Crowe (Bruce Willis). As Dr. Crowe delves deeper into the mysteries surrounding Cole's extraordinary gift, both therapist and patient are thrust into a startling journey that defies explanation, awakening them to a realm of the inexplicable.

Directed by: M. Night Shyamalan

American Beauty

ROTTEN TOMATOES: 87% CRITIC RATING | 93% AUDIENCE RATING

Lester Burnham (Kevin Spacey) leads a seemingly content life as a married man and father in the suburbs. However, his dissatisfaction with the monotonous and unfulfilling routine pushes him to make a bold decision. He walks away from his conventional job and embarks on a transformative journey to rediscover himself as a carefree and rebellious teenager, indulging in marijuana and shirking his responsibilities. This poignant and darkly comedic tale unfolds with a mix of cynicism and humor, ultimately culminating in a profoundly moving and uplifting turn of events.

Directed by: Sam Mendes

Fight Club

ROTTEN TOMATOES: 79% CRITIC RATING | 96% AUDIENCE RATING

In the grip of insomnia and deep melancholy, a despondent individual (Edward Norton) crosses paths with an enigmatic soap salesman named Tyler Durden (Brad Pitt). Drawn into Tyler's unconventional world, the man abandons his pristine existence when his immaculate apartment is reduced to ruins. Seeking refuge in Tyler's dilapidated abode, the two disillusioned souls establish an underground club governed by stringent regulations, where disenchanted men engage in physical altercations as an escape from their mundane lives. However, their once-perfect alliance begins to crumble when Marla (Helena Bonham Carter), a fellow interloper in their support group, captures Tyler's attention, leading to unforeseen consequences.

Directed by: David Fincher

The Matrix

ROTTEN TOMATOES: 88% CRITIC RATING | 85% AUDIENCE RATING

Neo (Keanu Reeves) is convinced that Morpheus (Laurence Fishburne), a mysterious and notorious figure, holds the key to unraveling the enigma known as the Matrix. Determined to uncover its true nature, Neo finds himself in the company of Trinity (Carrie-Anne Moss), a captivating stranger who guides him into a hidden realm. There, he encounters Morpheus and is thrust into a perilous struggle against a formidable group of relentless and cunning agents. As Neo and his allies fight fiercely for survival, they come face-to-face with a truth that carries a weight far greater than their very existence.

Directed by: The Wachowskis