The Best 25 Movies Of 1999 Ranked

1999 Movie poster collage
Everett Collection

Sometimes pegged the best year ever for film, of course, 1939 really holds that title but our staff members put their heads together to come up with a list of our favorite movies that were released in 1999.

Neck and neck almost to the finish line a full furlong ahead of the pack of theatrical movies were The Sixth Sense and Star Wars: Episode I — The Phantom Menace. A last-minute surge propelled The Sixth Sense across the line to win our poll, just as it did in the summer of 1999 at the box office.

Double Jeopardy came in third, followed by a tie for fourth between Analyze This and Austin Powers: The Spy Who Shagged Me. Fifth place went to Message In A Bottle. See where some of your favs may have placed.

Top 25 movies of 1999

1The Sixth Sense

In this chilling psychological thriller, 8-year-old Cole Sear is haunted by a dark secret: He is visited by ghosts. Confused by his paranormal powers, Cole is too young to understand his purpose and too afraid to tell anyone about his anguish, except child psychologist Dr. Malcolm Crowe. Stars Bruce Willis, Haley Joel Osment, Toni Collette and Olivia Williams.

2Star Wars: Episode I — The Phantom Menace

Young Anakin Skywalker comes under the tutelage of Obi-Wan Kenobi and his Jedi master, Qui-Gon Jinn. Stars Liam Neeson, Natalie Portman, Ewan McGregor and Jake Lloyd.

3Double Jeopardy

Framed for the murder of her husband, Libby Parsons survives the long years in prison with two burning desires sustaining her — finding her son and solving the mystery that destroyed her once happy life. Standing between her and her quest, however, is her parole officer, Travis Lehman. Stars Tommy Lee Jones, Ashley Judd, Bruce Greenwood and Annabeth Gish.

4Analyze This

New York’s most powerful gangster has been experiencing anxiety attacks and decides to see a shrink and get in touch with his feelings before a big mob conference. You try telling him his 50 minutes are up. Stars Robert De Niro, Billy Crystal, Lisa Kudrow and Chazz Palminteri.

5Austin Powers: The Spy Who Shagged Me

Double-O behave! Austin Powers must travel back in time to the swinging ’60s to recover his “mojo” — his life force and the source of his libido — which has been stolen by Dr. Evil in his plot to annihilate the world. Stars Mike Myers, Heather Graham, Michael York, Robert Wagner, Rob Lowe, Seth Green and Verne Troyer.

6Message In A Bottle

Following a hurtful divorce, a woman discovers a passionate letter in a bottle along a deserted stretch of coastline. The letter’s poetry and heartache prompt her to begin a search for the author that eventually leads her to a grief-stricken sailboat builder. Stars Kevin Costner, Robin Wright Penn, John Savage, Illeana Douglas, Robbie Coltrane and Paul Newman.

7American Beauty

In this bold look at suburban angst, middle-aged Lester Burnham, provoked by forbidden passions, makes a few changes in his rut of a life — including turning his lustful gaze toward his daughter’s sultry friend. Winner of five Academy Awards®, including Best Picture, Best Actor and Best Director. Stars Kevin Spacey, Annette Bening, Thora Birch, Wes Bentley, Mena Suvari and Chris Cooper.

8The Green Mile

Set on Death Row in a Southern prison in 1935, this is the big-screen adaptation of Stephen King’s 1996 bestselling serialized novel about a prison guard who develops a poignant relationship with one inmate who possesses a magical gift that is both mysterious and miraculous. Nominated for four Oscars®. Stars Tom Hanks, Michael Clarke Duncan, David Morse, Bonnie Hunt and James Cromwell.

9The Blair Witch Project

On October 21, 1994, Heather Donahue, Joshua Leonard and Michael Williams hiked into Maryland’s Black Hills Forest to shoot a documentary film on a local legend, “The Blair Witch.” They were never heard from again. One year later, their footage was found. Stars Heather Donahue, Michael Williams and Joshua Leonard.

10The Matrix

Keanu Reeves made a comeback of sorts after his post-Speed blockbuster drought in this futuristic action film that imagines there are two realities: one that consists of the life we live every day — and one that lies behind it. One is a dream; the other is The Matrix. Also stars Laurence Fishburne, Carrie-Anne Moss, Hugo Weaving and Joe Pantoliano.

11The Talented Mr. Ripley

To be young and carefree in Italy in the late 1950s — that’s the life Tom Ripley craves, and Dickie Greenleaf leads. When Dickie’s wealthy father asks Tom to bring his playboy son back to America, Dickie and his expatriate girlfriend never suspect the dangerous extremes to which Ripley will go to make their lifestyle his own. Stars Matt Damon, Gwyneth Paltrow, Jude Law, Cate Blanchett and Philip Seymour Hoffman.

12The Insider

Based on a true story, this Oscar®-nominated film follows tobacco company executive Jeffrey Wigand, who risks his career, his reputation and his family’s safety when he decides to go public about his employer’s concealment of the health dangers of its products. Stars Russell Crowe, Al Pacino, Christopher Plummer, Gina Gershon and Philip Baker Hall.

13Three Kings

A small group of adventurous American soldiers in Iraq at the end of the Gulf War is determined to steal a huge cache of gold reputed to be hidden somewhere near their desert base. Stars George Clooney, Mark Wahlberg, Ice Cube, Spike Jonze and Nora Dunn.

14Notting Hill

Anna Scott is the world’s most famous movie star. William Thacker owns a travel bookstore. For both people, something — or someone — seems to be missing. And when Anna’s and William’s paths unexpectedly cross in the eclectic neighborhood of Notting Hill, romance ensues. Stars Julia Roberts, Hugh Grant, Hugh Bonneville, Emma Chambers and James Dreyfus.

15Big Daddy

In an attempt to impress his girlfriend, slacker Sonny Koufax adopts a five-year-old boy, Julian, under the false pretense of being his biological father. When the plan doesn’t work out and Vanessa leaves him anyway, Sonny tries to “return” the kid to Social Services, but, much to his surprise, he falls for the kid and fights to keep him. Stars Adam Sandler, Joey Lauren Adams, Jon Stewart, Rob Schneider, Kristy Swanson, and Cole and Dylan Sprouse.

16American Pie

A group of friends, fed up with their well-deserved reputations as sexual no-hitters, decide to take action, each trying a different but equally outrageous approach to scoring with the female sex. Stars Jason Biggs, Shannon Elizabeth, Alyson Hannigan, Chris Klein and Natasha Lyonne.

17The Other Sister

In this uplifting and often bittersweet romantic comedy, 24-year-old Carla Tate is a slightly mentally challenged woman who, after years of special education, has successfully transcended many of her limitations — except that of her overprotective mother, Elizabeth. Defying her mother’s wishes, Carla embarks on a personal journey of self-discovery. Stars Juliette Lewis, Diane Keaton, Tom Skerritt, Giovanni Ribisi and Poppy Montgomery.


The heist goes smoothly enough. The cash is already hot. So when Porter and Val steal it, they’re in the clear. The time comes to split the take, and Val makes three grave mistakes: He takes Porter’s cut, he takes Porter’s wife and he tries to take Porter’s life. Porter soon resurfaces, reborn with a serious case of revenge. Stars Mel Gibson, Gregg Henry, Maria Bello, David Paymer, Deborah Kara Unger, William Devane and Kris Kristofferson.


Disney’s animated adventure is an innovative and entertaining exploration of the classic tale by Edgar Rice Burroughs and is filled with technological breakthroughs that bring the jungle to life as never before. Features the voices of Tony Goldwyn, Minnie Driver, Glenn Close, Lance Henriksen, Nigel Hawthorne and Wayne Knight.

20Tea With Mussolini

Taken from a chapter in the autobiography of acclaimed filmmaker Franco Zeffirelli, this film tells of Luca Innocenti and his struggle to assert his independence and find his way into a life of art. Eventually, Luca is raised by five rich unconventional women into a perfect gentleman. Stars Cher, Judi Dench, Joan Plowright, Maggie Smith and Lily Tomlin.

21Runaway Bride

Pretty Woman’s Julia Roberts and Richard Gere struck box-office gold again with this romantic comedy about Maggie Carpenter, a wannabe wife who has jilted so many grooms at the altar that she has become famous for it. Famous cynical reporter Ike Graham is writing about her latest engagement and wants to be there when it falls apart. But will he be the next victim? Also stars Joan Cusack, Hector Elizondo and Rita Wilson.

22The Out-Of-Towners

When a Midwestern couple flee their empty nest and head for the Big Apple, a comic odyssey of unexpected calamities yanks them through the most bizarre 24 hours of their lives. Based on an original screenplay by Neil Simon. Stars Steve Martin, Goldie Hawn, John Cleese, Mark McKinney and Oliver Hudson.

23Fight Club

Bored with being a cog in the corporate machine, a disaffected man gets a dose of excitement when he meets the charismatic Tyler Durden, a streetwise smart aleck who embraces life and manhood by getting into fistfights. Soon, Tyler and his new friend have launched an underground movement called Fight Club, which quickly sweeps through the nation’s basements and back alleys. Stars Brad Pitt, Edward Norton, Helena Bonham Carter, Meat Loaf and Jared Leto.

24The Mummy

In the 1920s, explorers unearth the ancient curse of evil Egyptian high priest Imhotep, whose awesome power takes corporeal form as the Mummy. Unless the explorers can stop him, the Mummy will gain total regeneration into an invincible force of evil. Based on the 1932 classic. Stars Brendan Fraser, Rachel Weisz, John Hannah, Arnold Vosloo and Kevin J. O’Connor.

25Music of The Heart

Roberta Guaspari leaves the security of her small hometown and moves to one of America’s toughest neighborhoods, East Harlem, to teach violin. At first, the kids, parents and the principal are skeptical. But Roberta teaches with such passion that soon her young violinists are making beautiful music, until the school board cuts her funding and others join the fight to keep it. Stars Meryl Streep, Aidan Quinn, Gloria Estefan and Angela Bassett.

Now for the full disclaimer, we made this list IN 1999! There are some huge cult favs that really should have made the cut, hello Office Space!? Or the two odd Tom Cruise films that came out, Magnolia or Eyes Wide Shut being the last movie from acclaimed director Stanley Kubrick You tell us: What did we miss from 25 years ago?

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