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List of 1999 Movies

Browse the full list of 1999 movies streaming online, including services like Netflix, Hulu, Prime Video, HBO and more. Sort by Rotten Tomatoes, IMDB rating, popularity and more to find something to watch!

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1. The Matrix

IMDB LogoIMDB Star
8.7/10
Rotten Tomatoes Logo88%
Reelgood Logo
97/100
Released: 1999Rated: R
Action & Adventure, Science-Fiction

What it's about: Set in the 22nd century, The Matrix tells the story of a computer hacker who joins a group of underground insurgents fighting the vast and powerful computers who now rule the earth.

Where to Watch: Available to stream on a popular subscription service (Hulu) & rent or buy from $2.99 on 6 services (iTunes, Prime Video & 4 others).

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2. Fight Club

IMDB LogoIMDB Star
8.8/10
Rotten Tomatoes Logo79%
Reelgood Logo
95/100
Released: 1999Rated: R
Drama, Cult

What it's about: A ticking-time-bomb insomniac and a slippery soap salesman channel primal male aggression into a shocking new form of therapy. Their concept catches on, with underground "fight clubs" forming in every town, until an eccentric gets in the way and ignites an out-of-control spiral toward oblivion.

Where to Watch: Available to stream on a subscription service (Cinemax), stream on a popular TV everywhere service (Cinemax) & rent or buy from $2.99 on 6 services (iTunes, Google Play & 4 others).

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3. American Beauty

IMDB LogoIMDB Star
8.3/10
Rotten Tomatoes Logo88%
Reelgood Logo
95/100
Released: 1999Rated: R
Drama

What it's about: Lester Burnham, a depressed suburban father in a mid-life crisis, decides to turn his hectic life around after developing an infatuation with his daughter's attractive friend.

Where to Watch: Available to stream on a popular subscription service (Hulu & CBS All Access), stream on a popular TV everywhere service (Epix) & rent or buy from $2.99 on 8 services (iTunes, Google Play & 6 others).

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4. The Sixth Sense

IMDB LogoIMDB Star
8.1/10
Rotten Tomatoes Logo86%
Reelgood Logo
93/100
Released: 1999Rated: PG-13
Drama, Mystery

What it's about: A psychological thriller about an eight year old boy named Cole Sear who believes he can see into the world of the dead. A child psychologist named Malcolm Crowe comes to Cole to help him deal with his problem, learning that he really can see ghosts of dead people.

Where to Watch: Available to stream on a popular subscription service (Netflix) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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5. The Green Mile

IMDB LogoIMDB Star
8.6/10
Rotten Tomatoes Logo79%
Reelgood Logo
91/100
Released: 1999Rated: R
Crime, Drama

What it's about: A supernatural tale set on death row in a Southern prison, where gentle giant John Coffey possesses the mysterious power to heal people's ailments. When the cell block's head guard, Paul Edgecomb, recognizes Coffey's miraculous gift, he tries desperately to help stave off the condemned man's execution.

Where to Watch: Available to rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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6. Toy Story 2

IMDB LogoIMDB Star
7.9/10
Rotten Tomatoes Logo100%
Reelgood Logo
89/100
Released: 1999Rated: G
Animation, Action & Adventure

What it's about: Andy heads off to Cowboy Camp, leaving his toys to their own devices. Things shift into high gear when an obsessive toy collector named Al McWhiggen, owner of Al's Toy Barn kidnaps Woody. Andy's toys mount a daring rescue mission, Buzz Lightyear meets his match and Woody has to decide where he and his heart truly belong.

Where to Watch: Available to rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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7. The Iron Giant

IMDB LogoIMDB Star
8.0/10
Rotten Tomatoes Logo96%
Reelgood Logo
88/100
Released: 1999Rated: PG
Animation, Action & Adventure

What it's about: In the small town of Rockwell, Maine in October 1957, a giant metal machine befriends a nine-year-old boy and ultimately finds its humanity by unselfishly saving people from their own fears and prejudices.

Where to Watch: Available to watch free online (Vudu) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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8. Being John Malkovich

IMDB LogoIMDB Star
7.7/10
Rotten Tomatoes Logo93%
Reelgood Logo
86/100
Released: 1999Rated: R
Comedy, Drama

What it's about: One day at work, unsuccessful puppeteer Craig finds a portal into the head of actor John Malkovich. The portal soon becomes a passion for anybody who enters it's mad and controlling world of overtaking another human body.

Where to Watch: Available to stream on a subscription service (Cinemax), stream on a popular TV everywhere service (Cinemax) & rent or buy from $2.99 on 8 services (iTunes, Google Play & 6 others).

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9. Tarzan

IMDB LogoIMDB Star
7.3/10
Rotten Tomatoes Logo89%
Reelgood Logo
85/100
Released: 1999Rated: G
Animation, Action & Adventure

What it's about: Tarzan was a small orphan who was raised by an ape named Kala since he was a child. He believed that this was his family, but on an expedition Jane Porter is rescued by Tarzan. He then finds out that he's human. Now Tarzan must make the decision as to which family he should belong to...

Where to Watch: Available to stream on a popular subscription service (Netflix), stream on a TV everywhere service (Freeform) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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10. Office Space

IMDB LogoIMDB Star
7.7/10
Rotten Tomatoes Logo80%
Reelgood Logo
85/100
Released: 1999Rated: R
Comedy, Cult

What it's about: Three office workers strike back at their evil employers by hatching a hapless attempt to embezzle money.

Where to Watch: Available to rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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11. Magnolia

IMDB LogoIMDB Star
8.0/10
Rotten Tomatoes Logo83%
Reelgood Logo
84/100
Released: 1999Rated: R
Drama

What it's about: An epic mosaic of many interrelated characters in search of happiness, forgiveness, and meaning in the San Fernando Valley.

Where to Watch: Available to rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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12. The Talented Mr. Ripley

IMDB LogoIMDB Star
7.4/10
Rotten Tomatoes Logo83%
Reelgood Logo
84/100
Released: 1999Rated: R
Crime, LGBTQ

What it's about: Tom Ripley is a calculating young man who believes it's better to be a fake somebody than a real nobody. Opportunity knocks in the form of a wealthy U.S. shipbuilder who hires Tom to travel to Italy to bring back his playboy son, Dickie. Ripley worms his way into the idyllic lives of Dickie and his girlfriend, plunging into a daring scheme of duplicity, lies and murder.

Where to Watch: Available to stream on a popular subscription service (Prime Video & Hulu), stream on a popular TV everywhere service (Epix) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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13. October Sky

IMDB LogoIMDB Star
7.8/10
Rotten Tomatoes Logo91%
Reelgood Logo
84/100
Released: 1999Rated: PG
Biography, Drama

What it's about: Based on the true story of Homer Hickam, a coal miner's son who was inspired by the first Sputnik launch to take up rocketry against his father's wishes, and eventually became a NASA scientist.

Where to Watch: Available to stream on a popular subscription service (HBO), stream on a popular TV everywhere service (HBO) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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14. Sleepy Hollow

IMDB LogoIMDB Star
7.3/10
Rotten Tomatoes Logo68%
Reelgood Logo
84/100
Released: 1999Rated: R
Horror, Drama

What it's about: New York detective Ichabod Crane is sent to Sleepy Hollow to investigate a series of mysterious deaths in which the victims are found beheaded. But the locals believe the culprit to be none other than the ghost of the legendary Headless Horseman.

Where to Watch: Available to stream on a popular TV everywhere service (Sundance & Epix) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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15. Notting Hill

IMDB LogoIMDB Star
7.1/10
Rotten Tomatoes Logo83%
Reelgood Logo
83/100
Released: 1999Rated: PG-13
Comedy, Drama

What it's about: William Thacker is a London bookstore owner whose humdrum existence is thrown into romantic turmoil when famous American actress Anna Scott appears in his shop. A chance encounter over spilled orange juice leads to a kiss that blossoms into a full-blown affair. As the average bloke and glamorous movie star draw closer and closer together, they struggle to reconcile their radically different lifestyles in the name of love.

Where to Watch: Available to stream on a popular subscription service (HBO), stream on a popular TV everywhere service (HBO) & rent or buy from $2.99 on 8 services (iTunes, Google Play & 6 others).

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16. The Mummy

IMDB LogoIMDB Star
7.0/10
Rotten Tomatoes Logo59%
Reelgood Logo
82/100
Released: 1999Rated: PG-13
Action & Adventure, Fantasy

What it's about: Dashing legionnaire Rick O'Connell stumbles upon the hidden ruins of Hamunaptra while in the midst of a battle to claim the area in 1920s Egypt. It has been over three thousand years since former High Priest Imhotep suffered a fate worse than death as a punishment for a forbidden love—along with a curse that guarantees eternal doom upon the world if he is ever awoken.

Where to Watch: Available to stream on a popular subscription service (Prime Video) & rent or buy from $1.99 on 7 services (iTunes, Google Play & 5 others).

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17. The Insider

IMDB LogoIMDB Star
7.8/10
Rotten Tomatoes Logo96%
Reelgood Logo
82/100
Released: 1999Rated: R
Biography, Drama

What it's about: Tells the true story of a 60 Minutes television series exposé of the tobacco industry, as seen through the eyes of a real tobacco executive, Jeffrey Wigand.

Where to Watch: Available to rent or buy from $2.99 on 6 services (iTunes, Google Play & 4 others).

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18. Boys Don't Cry

IMDB LogoIMDB Star
7.5/10
Rotten Tomatoes Logo88%
Reelgood Logo
82/100
Released: 1999Rated: R
Biography, LGBTQ

What it's about: Female born, Teena Brandon adopts his male identity of Brandon Teena and attempts to find himself and love in Nebraska.

Where to Watch: Available to stream on a popular subscription service (HBO), stream on a popular TV everywhere service (HBO) & rent or buy from $2.99 on 6 services (iTunes, Google Play & 4 others).

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19. Election

IMDB LogoIMDB Star
7.2/10
Rotten Tomatoes Logo92%
Reelgood Logo
82/100
Released: 1999Rated: R
Comedy, Drama

What it's about: A high school teacher's personal life becomes complicated as he works with students during the school elections.

Where to Watch: Available to stream on a popular subscription service (Hulu), stream on a popular TV everywhere service (Epix) & rent or buy from $2.99 on 6 services (iTunes, Google Play & 4 others).

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20. All About My Mother

IMDB LogoIMDB Star
7.8/10
Rotten Tomatoes Logo98%
Reelgood Logo
82/100
Released: 1999Rated: R
Comedy, Drama

What it's about: A single mother in Madrid sees her only son die on his birthday as he runs to seek an actress' autograph. Beside herself with grief, she returns to Barcelona to tell the boy's father about the death of the son he never knew he had.

Where to Watch: Available to rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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21. Three Kings

IMDB LogoIMDB Star
7.1/10
Rotten Tomatoes Logo94%
Reelgood Logo
81/100
Released: 1999Rated: R
Action & Adventure, Comedy

What it's about: A group of American soldiers stationed in Iraq at the end of the Gulf War find a map they believe will take them to a huge cache of stolen Kuwaiti gold hidden near their base, and they embark on a secret mission that's destined to change everything.

Where to Watch: Available to rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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22. Eyes Wide Shut

IMDB LogoIMDB Star
7.4/10
Rotten Tomatoes Logo75%
Reelgood Logo
81/100
Released: 1999Rated: R
Drama, Mystery

What it's about: After Dr. Bill Harford's wife, Alice, admits to having sexual fantasies about a man she met, Bill becomes obsessed with having a sexual encounter. He discovers an underground sexual group and attends one of their meetings -- and quickly discovers that he is in over his head.

Where to Watch: Available to rent or buy from $1.99 on 8 services (iTunes, Google Play & 6 others).

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23. The Virgin Suicides

IMDB LogoIMDB Star
7.2/10
Rotten Tomatoes Logo76%
Reelgood Logo
81/100
Released: 1999Rated: R
Drama, Romance

What it's about: A group of male friends become obsessed with five mysterious sisters who are sheltered by their strict, religious parents.

Where to Watch: Available to watch free online (Sony Crackle & PopcornFlix), stream on a popular subscription service (Prime Video, Showtime & Kanopy), stream on a popular TV everywhere service (Showtime & Epix) & rent or buy from $2.99 on 6 services (iTunes, Google Play & 4 others).

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24. Galaxy Quest

IMDB LogoIMDB Star
7.3/10
Rotten Tomatoes Logo90%
Reelgood Logo
81/100
Released: 1999Rated: PG
Action & Adventure, Comedy

What it's about: The stars of a 1980s sci-fi show—now eking out a living through re-runs and sci-fi conventions—are beamed aboard an alien spacecraft. Believing the cast's heroic on-screen dramas are historical documents of real-life adventures, the band of aliens turn to the cast members for help in their quest to overcome the oppressive regime in their solar system.

Where to Watch: Available to rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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25. The Straight Story

IMDB LogoIMDB Star
8.0/10
Rotten Tomatoes Logo96%
Reelgood Logo
81/100
Released: 1999Rated: G
Biography, Independent

What it's about: A retired farmer and widower in his 70s, Alvin Straight learns one day that his distant brother Lyle has suffered a stroke and may not recover. Alvin is determined to make things right with Lyle while he still can, but his brother lives in Wisconsin, while Alvin is stuck in Iowa with no car and no driver's license. Then he hits on the idea of making the trip on his old lawnmower, thus beginning a picturesque and at times deeply spiritual odyssey.

Where to Watch: Available to rent or buy from $2.99 on 5 services (iTunes, Google Play & 3 others).

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26. South Park: Bigger, Longer & Uncut

IMDB LogoIMDB Star
7.7/10
Rotten Tomatoes Logo81%
Reelgood Logo
80/100
Released: 1999Rated: R
Comedy, Animation

What it's about: When the four boys see an R-rated movie featuring Canadians Terrance and Philip, they are pronounced "corrupted", and their parents pressure the United States to wage war against Canada.

Where to Watch: Available to rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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kanopy

27. The Boondock Saints

IMDB LogoIMDB Star
7.8/10
Rotten Tomatoes Logo22%
Reelgood Logo
80/100
Released: 1999Rated: R
Action & Adventure, Crime

What it's about: With a God-inspired moral obligation to act against evil, twin brothers Conner and Murphy set out to rid Boston of criminals. However, rather than working within the system, these Irish Americans decide to take swift retribution into their own hands.

Where to Watch: Available to watch free online (Tubi TV), stream on a popular subscription service (Prime Video & Kanopy) & rent or buy from $2.99 on 6 services (iTunes, Google Play & 4 others).

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28. 10 Things I Hate About You

IMDB LogoIMDB Star
7.3/10
Rotten Tomatoes Logo68%
Reelgood Logo
80/100
Released: 1999Rated: PG-13
Comedy, Drama

What it's about: On the first day at his new school, Cameron instantly falls for Bianca, the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date until her ill-tempered, completely un-dateable older sister Kat goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy with a nasty reputation of his own.

Where to Watch: Available to rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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29. Girl, Interrupted

IMDB LogoIMDB Star
7.3/10
Rotten Tomatoes Logo54%
Reelgood Logo
80/100
Released: 1999Rated: R
Drama, Biography

What it's about: Set in the changing world of the late 1960s, Susanna Kaysen's prescribed "short rest" from a psychiatrist she had met only once becomes a strange, unknown journey into Alice's Wonderland, where she struggles with the thin line between normal and crazy. Susanna soon realizes how hard it is to get out once she has been committed, and she ultimately has to choose between the world of people who belong inside or the difficult world of reality outside.

Where to Watch: Available to watch free online (Sony Crackle & Vudu) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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30. The Hurricane

IMDB LogoIMDB Star
7.6/10
Rotten Tomatoes Logo83%
Reelgood Logo
79/100
Released: 1999Rated: R
Biography, Drama

What it's about: The story of Rubin "Hurricane" Carter, a boxer wrongly imprisoned for murder, and the people who aided in his fight to prove his innocence.

Where to Watch: Available to stream on a popular subscription service (Starz), stream on a popular TV everywhere service (Starz) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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31. American Pie

IMDB LogoIMDB Star
7.0/10
Rotten Tomatoes Logo61%
Reelgood Logo
78/100
Released: 1999Rated: R
Comedy, Romance

What it's about: At a high-school party, four friends find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to all "score." by their senior prom.

Where to Watch: Available to stream on a subscription service (Cinemax), stream on a popular TV everywhere service (Cinemax) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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32. Go

IMDB LogoIMDB Star
7.2/10
Rotten Tomatoes Logo91%
Reelgood Logo
78/100
Released: 1999Rated: R
Comedy, Crime

What it's about: Told from three perspectives, a story of a bunch of young Californians trying to get some cash, do and deal some drugs, score money and sex in Las Vegas, and generally experience the rush of life.

Where to Watch: Available to watch free online (Sony Crackle) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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cbs_all_access

33. The Blair Witch Project

IMDB LogoIMDB Star
6.5/10
Rotten Tomatoes Logo87%
Reelgood Logo
78/100
Released: 1999Rated: R
Horror, Cult

What it's about: In October of 1994 three student filmmakers disappeared in the woods near Burkittsville, Maryland, while shooting a documentary. A year later their footage was found.

Where to Watch: Available to stream on a popular subscription service (Starz & CBS All Access), stream on a popular TV everywhere service (Starz) & rent or buy from $1.99 on 8 services (iTunes, Google Play & 6 others).

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34. Ghost Dog: The Way of the Samurai

IMDB LogoIMDB Star
7.5/10
Rotten Tomatoes Logo82%
Reelgood Logo
78/100
Released: 1999Rated: R
Action & Adventure, Crime

What it's about: An African-American Mafia hit man who models himself after the samurai of old finds himself targeted for death by the mob.

Where to Watch: Available to rent or buy from $1.99 on 3 services (Microsoft, Vudu & PlayStation Store).

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35. Cruel Intentions

IMDB LogoIMDB Star
6.8/10
Rotten Tomatoes Logo54%
Reelgood Logo
77/100
Released: 1999Rated: R
Drama, Romance

What it's about: Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.

Where to Watch: Available to stream on a popular subscription service (Showtime), stream on a popular TV everywhere service (Showtime) & rent or buy from $2.99 on 1 service (PlayStation Store).

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36. Following

IMDB LogoIMDB Star
7.5/10
Rotten Tomatoes Logo80%
Reelgood Logo
77/100
Released: 1999Rated: R
Mystery, Independent

What it's about: A struggling, unemployed young writer takes to following strangers around the streets of London, ostensibly to find inspiration for his new novel.

Where to Watch: Available to stream on a subscription service (The Criterion Channel) & rent or buy from $2.99 on 5 services (iTunes, Google Play & 3 others).

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37. Star Wars: Episode I - The Phantom Menace

IMDB LogoIMDB Star
6.5/10
Rotten Tomatoes Logo53%
Reelgood Logo
76/100
Released: 1999Rated: PG
Action & Adventure, Fantasy

What it's about: Anakin Skywalker, a young slave strong with the Force, is discovered on Tatooine. Meanwhile, the evil Sith have returned, enacting their plot for revenge against the Jedi.

Where to Watch: Available to rent or buy from $19.99 on 8 services (iTunes, Google Play & 6 others).

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38. Man on the Moon

IMDB LogoIMDB Star
7.4/10
Rotten Tomatoes Logo63%
Reelgood Logo
76/100
Released: 1999Rated: R
Biography, Stand-up & Talk

What it's about: A film about the life and career of the eccentric avant-garde comedian, Andy Kaufman.

Where to Watch: Available to stream on a popular subscription service (Starz), stream on a popular TV everywhere service (Starz) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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39. The Cider House Rules

IMDB LogoIMDB Star
7.4/10
Rotten Tomatoes Logo71%
Reelgood Logo
76/100
Released: 1999Rated: PG-13
Drama, Romance

What it's about: Homer is an orphan who was never adopted, becoming the favorite of orphanage director Dr. Larch. Dr. Larch imparts his full medical knowledge on Homer, who becomes a skilled, albeit unlicensed, physician. But Homer yearns for a self-chosen life outside the orphanage. What will Homer learn about life and love in the cider house? What of the destiny that Dr. Larch has planned for him?

Where to Watch: Available to stream on a popular subscription service (Starz), stream on a popular TV everywhere service (Starz) & rent or buy from $1.99 on 7 services (iTunes, Google Play & 5 others).

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40. The Thomas Crown Affair

IMDB LogoIMDB Star
6.8/10
Rotten Tomatoes Logo70%
Reelgood Logo
76/100
Released: 1999Rated: R
Crime, Romance

What it's about: A very rich and successful playboy amuses himself by stealing artwork, but may have met his match in a seductive detective.

Where to Watch: Available to stream on a subscription service (Cinemax), stream on a popular TV everywhere service (Cinemax & Epix) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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41. Austin Powers: The Spy Who Shagged Me

IMDB LogoIMDB Star
6.6/10
Rotten Tomatoes Logo52%
Reelgood Logo
75/100
Released: 1999Rated: PG-13
Comedy, Action & Adventure

What it's about: When diabolical genius, Dr. Evil travels back in time to steal superspy Austin Powers's ‘mojo’, Austin must return to the swingin' '60s himself – with the help of American agent, Felicity Shagwell – to stop the dastardly plan. Once there, Austin faces off against Dr. Evil's army of minions and saves the world in his own unbelievably groovy way.

Where to Watch: Available to rent or buy from $3.99 on 6 services (iTunes, Google Play & 4 others).

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amazon_prime
epix
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42. The Limey

IMDB LogoIMDB Star
7.0/10
Rotten Tomatoes Logo93%
Reelgood Logo
75/100
Released: 1999Rated: R
Crime, Drama

What it's about: The Limey follows Wilson, a tough English ex-con who travels to Los Angeles to avenge his daughter's death. Upon arrival, Wilson goes to task battling Valentine and an army of L.A.'s toughest criminals, hoping to find clues and piece together what happened. After surviving a near-death beating, getting thrown from a building and being chased down a dangerous mountain road, the Englishman decides to dole out some bodily harm of his own.

Where to Watch: Available to watch free online (Tubi TV), stream on a popular subscription service (Prime Video & Tribeca Short List), stream on a popular TV everywhere service (Epix) & rent or buy from $2.99 on 6 services (iTunes, Google Play & 4 others).

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43. One Day in September

IMDB LogoIMDB Star
7.8/10
Rotten Tomatoes Logo97%
Reelgood Logo
74/100
Released: 1999Rated: R
Documentary, History

What it's about: The full story of the 1972 Munich Olympics Massacre and the Israeli revenge operation 'Wrath of God.' The 1972 Munich Olympics were interrupted by Palestinian terrorists taking Israeli athletes hostage. Besides footage taken at the time, we see interviews with the surviving terrorist, Jamal Al Gashey, and various officials detailing exactly how the police, lacking an anti-terrorist squad and turning down help from the Israelis, botched the operation

Where to Watch: Available to stream on a popular subscription service (Prime Video) & rent or buy from $0.99 on 1 service (Prime Video).

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44. Any Given Sunday

IMDB LogoIMDB Star
6.9/10
Rotten Tomatoes Logo52%
Reelgood Logo
74/100
Released: 1999Rated: R
Drama, Sport

What it's about: A star quarterback gets knocked out of the game and an unknown third stringer is called in to replace him. The unknown gives a stunning performance and forces the aging coach to reevaluate his game plans and life. A new co-owner/president adds to the pressure of winning. The new owner must prove her self in a male dominated world.

Where to Watch: Available to watch free online (Vudu) & rent or buy from $2.99 on 5 services (Google Play, Microsoft & 3 others).

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cinemax

45. Analyze This

IMDB LogoIMDB Star
6.7/10
Rotten Tomatoes Logo70%
Reelgood Logo
74/100
Released: 1999Rated: R
Comedy, Crime

What it's about: Countless wiseguy films are spoofed in this film that centers on the neuroses and angst of a powerful Mafia racketeer who suffers from panic attacks. When Paul Vitti needs help dealing with his role in the "family," unlucky shrink Dr. Ben Sobel is given just days to resolve Vitti's emotional crisis and turn him into a happy, well-adjusted gangster.

Where to Watch: Available to stream on a subscription service (Cinemax), stream on a popular TV everywhere service (Cinemax) & rent or buy from $2.99 on 5 services (iTunes, Google Play & 3 others).

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free
fandor
shoutfactorytv
+ 1

46. My Best Fiend

IMDB LogoIMDB Star
7.9/10
Rotten Tomatoes Logo80%
Reelgood Logo
73/100
Released: 1999
Documentary, Biography

What it's about: A film that describes the love-hate relationship between Werner Herzog and Klaus Kinski, the deep trust between the director and the actor, and their independently and simultaneously hatched plans to murder one another.

Where to Watch: Available to watch free online (Tubi TV), stream on a subscription service (Fandor, Shout Factory TV & The Criterion Channel) & rent or buy from $2.99 on 4 services (iTunes, Prime Video & 2 others).

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starz
epix

47. Stir of Echoes

IMDB LogoIMDB Star
7.0/10
Rotten Tomatoes Logo67%
Reelgood Logo
73/100
Released: 1999Rated: R
Thriller, Horror

What it's about: After being hypnotized by his sister in law, Tom Witzky begins seeing haunting visions of a girl's ghost and a mystery begins to unfold around her.

Where to Watch: Available to stream on a popular subscription service (Starz), stream on a popular TV everywhere service (Starz & Epix) & rent or buy from $1.99 on 7 services (iTunes, Google Play & 5 others).

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Rent/Buy

48. Buena Vista Social Club

IMDB LogoIMDB Star
7.6/10
Rotten Tomatoes Logo91%
Reelgood Logo
73/100
Released: 1999Rated: G
Documentary, Independent

What it's about: In this fascinating Oscar-nominated documentary, American guitarist Ry Cooder brings together a group of legendary Cuban folk musicians (some in their 90s) to record a Grammy-winning CD in their native city of Havana. The result is a spectacular compilation of concert footage from the group's gigs in Amsterdam and New York City's famed Carnegie Hall, with director Wim Wenders capturing not only the music -- but also the musicians' life stories.

Where to Watch: Available to rent or buy from $2.99 on 4 services (iTunes, Google Play & 2 others).

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epix

49. Payback

IMDB LogoIMDB Star
7.1/10
Rotten Tomatoes Logo54%
Reelgood Logo
73/100
Released: 1999Rated: R
Action & Adventure, Thriller

What it's about: With friends like these, who needs enemies? That's the question bad guy Porter is left asking after his wife and partner steal his heist money and leave him for dead -- or so they think. Five months and an endless reservoir of bitterness later, Porter's partners and the crooked cops on his tail learn how bad payback can be.

Where to Watch: Available to stream on a popular TV everywhere service (Epix) & rent or buy from $2.99 on 2 services (Google Play & PlayStation Store).

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Rent/Buy

50. eXistenZ

IMDB LogoIMDB Star
6.8/10