Quiz: How Many of These 1999 Movies Can You Identify?

It’s 2019, which means all of the movies in this quiz turn 20 years old this year. So how many of these 1999 movies can you identify? Some of them are iconic, and anyone should be able to guess them. Others are a little harder to remember. And a few of them you probably won’t remember even if you saw them…

It’s 2019, which means all of the movies in this quiz turn 20 years old this year. So how many of these 1999 movies can you identify? Some of them are iconic, and anyone should be able to guess them. Others are a little harder to remember. And a few of them you probably won’t remember even if you saw them…

What 1999 movie is this?

  • Star Wars: The Empire Strikes Back
  • Star Wars: The Phantom Menace
  • Star Wars: The Force Awakens
  • Star Wars: Super Laser Sword Fighters

"The Phantom Menace" finally gave kids what they really wanted: a movie about a trade embargo.

"The Phantom Menace" finally gave kids what they really wanted: a movie about a trade embargo.

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What 1999 movie is this?

  • The Last American Virgin
  • American Pie
  • Porky's
  • Fast Times at Ridgemont High

Jason Biggs could cure cancer tomorrow but he'll still be known best as the kid who f***ed a pie.

Jason Biggs could cure cancer tomorrow but he'll still be known best as the kid who f***ed a pie.

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What 1999 movie is this?

  • Drop Dead Gorgeous
  • Eyes Wide Shut
  • American Beauty
  • Brokedown Palace

Everyone agrees "American Beauty" is dreadful, and there's no way to explain why we all liked it in 1999.

Everyone agrees "American Beauty" is dreadful, and there's no way to explain why we all liked it in 1999.

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What 1999 movie is this?

  • The Matrix
  • Johnny Mnemonic
  • The Devil's Advocate
  • Speed

"The Matrix" is a movie about a red pill, birthing an entire online subculture of society's worst people.

"The Matrix" is a movie about a red pill, birthing an entire online subculture of society's worst people.

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What 1999 movie is this?

  • Man on the Moon
  • Arlington Road
  • Office Space
  • Deuce Bigalow: Male Gigolo

The details changed — Staplers? Fax machines? What are they? — but office ennui is timeless.

The details changed — Staplers? Fax machines? What are they? — but office ennui is timeless.

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What 1999 movie is this?

  • The Blair Witch Project
  • Idle Hands
  • The Haunting
  • The Sixth Sense

M. Night Shyamalan has made 74 movies since "The Sixth Sense," and all of them are putrid.

M. Night Shyamalan has made 74 movies since "The Sixth Sense," and all of them are putrid.

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What 1999 movie is this?

  • The World Is Not Enough
  • Tomorrow Never Dies
  • Die Another Day
  • GoldenEye

Apart from "GoldenEye," every Brosnan Bond flick is interchangeable. No one knows which one is which.

Apart from "GoldenEye," every Brosnan Bond flick is interchangeable. No one knows which one is which.

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What 1999 movie is this?

  • The End of the Affair
  • Mansfield Park
  • An Ideal Husband
  • The Talented Mr. Ripley

The first cinematic adaptation of "The Talented Mr. Ripley" was the 1960 French film "Purple Noon."

The first cinematic adaptation of "The Talented Mr. Ripley" was the 1960 French film "Purple Noon."

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What 1999 movie is this?

  • Austin Powers: International Man of Mystery
  • Austin Powers: The Spy Who Shagged Me
  • Austin Powers: License to Swing
  • Austin Powers in Goldmember

There have been rumors for years of an impending fourth "Austin Powers" film. God help us all.

There have been rumors for years of an impending fourth "Austin Powers" film. God help us all.

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What 1999 movie is this?

  • Toy Story
  • Toy Story 2
  • Toy Story 3
  • Toy Story 4

It's going to take an extinction level event to get them to stop making "Toy Story" sequels.

It's going to take an extinction level event to get them to stop making "Toy Story" sequels.

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What 1999 movie is this?

  • Good Burger
  • American Pie
  • 10 Things I Hate About You
  • She's All That

Ah, yes, the movie that thinks you'll believe Rachael Leigh Cook is unattractive if she's wearing glasses.

Ah, yes, the movie that thinks you'll believe Rachael Leigh Cook is unattractive if she's wearing glasses.

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What 1999 movie is this?

  • Stepmom
  • Notting Hill
  • Runaway Bride
  • Erin Brockovich

You're forgiven if you don't know the difference between "Notting Hill" and those three other films.

You're forgiven if you don't know the difference between "Notting Hill" and those three other films.

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What 1999 movie is this?

  • She's All That
  • American Pie
  • 10 Things I Hate About You
  • Cruel Intentions

Sorry, "Clueless" fans, but "10 Things I Hate About You" is the best teen movie of the '90s. Don't @ me.

Sorry, "Clueless" fans, but "10 Things I Hate About You" is the best teen movie of the '90s. Don't @ me.

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What 1999 movie is this?

  • Threesome
  • Three Can Play at That Game
  • Three's a Crowd
  • Three to Tango

I know you think I made "Three to Tango" up, but I swear to God it is a real movie that really exists.

I know you think I made "Three to Tango" up, but I swear to God it is a real movie that really exists.

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What 1999 movie is this?

  • A Walk in the Clouds
  • Kings of New England
  • Mystery, Alaska
  • The Cider House Rules

One of many films that could've been good if not for the relentlessly creepy presence of Tobey Maguire.

One of many films that could've been good if not for the relentlessly creepy presence of Tobey Maguire.

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What 1999 movie is this?

  • Any Given Sunday
  • Sunday Night Football
  • Sunday, Sunday, Sunday
  • Sunday Is for Football

The movie that answers the question: When did Al Pacino become a complete caricature of himself?

The movie that answers the question: When did Al Pacino become a complete caricature of himself?

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What 1999 movie is this?

  • Who Let That Mouse in Here?
  • MouseHunt
  • Stuart Little
  • House Mouse

If only E.B. White had had the imagination to write Stuart Little as a rad skateboarder or whatever.

If only E.B. White had had the imagination to write Stuart Little as a rad skateboarder or whatever.

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What 1999 movie is this?

  • The Truman Show
  • Reality Bites
  • EDtv
  • Stay Tuned

This movie came out after "The Truman Show," and it's a lot like "The Truman Show" but even worse.

This movie came out after "The Truman Show," and it's a lot like "The Truman Show" but even worse.

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What 1999 movie is this?

  • Anna and the King
  • The King and I
  • The King and Anna
  • Anna and the King of Siam

For people who love legendary musical "The King and I" but just wish it didn't have all that music.

For people who love legendary musical "The King and I" but just wish it didn't have all that music.

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What 1999 movie is this?

  • Inside Man
  • On the Inside
  • Getting Inside
  • The Insider

Sit there for two hours and watch a bunch of suits talk to each other about how cigarettes are bad.

Sit there for two hours and watch a bunch of suits talk to each other about how cigarettes are bad.

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What 1999 movie is this?

  • Idle Hands
  • Stir of Echoes
  • House on Haunted Hill
  • Hollow Man

"Stir of Echoes" is a 1999 horror movie that literally no one remembers except my older brother Dave.

"Stir of Echoes" is a 1999 horror movie that literally no one remembers except my older brother Dave.

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What 1999 movie is this?

  • Sesame Street: Elmo's Space Adventure
  • Sesame Street Presents: Follow That Monster!
  • The Adventures of Elmo in Grouchland
  • Sesame Street: Bigger, Longer and Uncut

It's "Follow That Bird" except instead of the most lovable "Sesame Street" character, it has Elmo.

It's "Follow That Bird" except instead of the most lovable "Sesame Street" character, it has Elmo.

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What 1999 movie is this?

  • Miss Congeniality
  • But I'm a Cheerleader
  • Jawbreaker
  • Drop Dead Gorgeous

People dunk on Denise Richards for some reason, but she rules. And "Drop Dead Gorgeous" is why.

People dunk on Denise Richards for some reason, but she rules. And "Drop Dead Gorgeous" is why.

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What 1999 movie is this?

  • Entrapment
  • Double Jeopardy
  • Malice
  • She Dips Beneath Lasers

This is one of those movies you paid $10 to watch even though you were interested in only one scene.

This is one of those movies you paid $10 to watch even though you were interested in only one scene.

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What 1999 movie is this?

  • Lost and Found
  • There and Back
  • Truth and Romance
  • Here and Now

"Three to Tango" is a real movie, but we made this one up. There's no such movie as "Lost and Found."

"Three to Tango" is a real movie, but we made this one up. There's no such movie as "Lost and Found."

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What 1999 movie is this?

  • Meet Joe Black
  • Fight Club
  • Spy Game
  • Ocean’s Eleven

Although its iconic in its memory today, the film adaptation of Chuck Palahniuk’s novel “Fight Club” was a total box office bomb in 1999, grossing only $37 million from its $63 million budget.

Although its iconic in its memory today, the film adaptation of Chuck Palahniuk’s novel “Fight Club” was a total box office bomb in 1999, grossing only $37 million from its $63 million budget.

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What 1999 movie is this?

  • Interview with the Vampire
  • Without Limits
  • The Others
  • Magnolia

Director Paul Thomas Anderson followed up the success of “Boogie Nights” with the epic drama “Magnolia,” which starred just about every ‘90s box office draw you can think of, including Julianne Moore, Philip Seymour Hoffman, John C. Reilly and Tom Cruise.

Director Paul Thomas Anderson followed up the success of “Boogie Nights” with the epic drama “Magnolia,” which starred just about every ‘90s box office draw you can think of, including Julianne Moore, Philip Seymour Hoffman, John C. Reilly and Tom Cruise.

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What 1999 movie is this?

  • Heartwood
  • Million Dollar Baby
  • Boys Don’t Cry
  • Insomnia

“Boys Don’t Cry” was way ahead of its time. Hilary Swank earned her first Oscar the following year for her role as a transgeder man. Chloë Sevigny starred alongside her, making this movie a must watch for any film fan.

“Boys Don’t Cry” was way ahead of its time. Hilary Swank earned her first Oscar the following year for her role as a transgeder man. Chloë Sevigny starred alongside her, making this movie a must watch for any film fan.

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What 1999 movie is this?

  • The Best Man
  • How Stella Got Her Groove Back
  • He Got Game
  • She’s Gotta Have It

Malcolm D. Lee’s directorial debut made nearly four times its $9 million budget, reminding everyone that inclusivity in film is totally necessary. This rom-com still holds up, unlike others from the ‘90s.

Malcolm D. Lee’s directorial debut made nearly four times its $9 million budget, reminding everyone that inclusivity in film is totally necessary. This rom-com still holds up, unlike others from the ‘90s.

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What 1999 movie is this?

  • Ferngully
  • The Iron Giant
  • Jetsons: The Movie
  • The Steel Giant

“The Iron Giant” became an instant animated movie classic, marking one of the last great traditionally animated films. Just kidding, the Giant was animated almost entirely using CGI, but it could’ve fooled you, huh?

“The Iron Giant” became an instant animated movie classic, marking one of the last great traditionally animated films. Just kidding, the Giant was animated almost entirely using CGI, but it could’ve fooled you, huh?

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What 1999 movie is this?

  • Galaxy Quest
  • Star Trek: Voyager
  • Star Trek: Enterprise
  • Alien

What makes “Galaxy Quest” the best sci-fi parody movie of all time is its incredible cast. Casting Sigourney Weaver to joke on her “Alien” role was a stroke of genius and Alan Rickman’s chops are enough to carry any film.

What makes “Galaxy Quest” the best sci-fi parody movie of all time is its incredible cast. Casting Sigourney Weaver to joke on her “Alien” role was a stroke of genius and Alan Rickman’s chops are enough to carry any film.

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What 1999 movie is this?

  • Pleasantville
  • Best Laid Plans
  • Simply Irresistible
  • Cruel Intentions

“Cruel Intentions” is like the R-rated version of “Gossip Girl” with some ‘90s powerhouses in the cast. Reese Witherspoon, Sarah Michelle Gellar, Selma Blair and Ryan Phillippe gave audiences something to talk about and earned this movie over $70 million at the box office.

“Cruel Intentions” is like the R-rated version of “Gossip Girl” with some ‘90s powerhouses in the cast. Reese Witherspoon, Sarah Michelle Gellar, Selma Blair and Ryan Phillippe gave audiences something to talk about and earned this movie over $70 million at the box office.

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What 1999 movie is this?

  • In The Loop
  • The Campaign
  • Election
  • Vice

“Election” still holds up as one of the most brutally honest portrayals of high school politics on film and probably says more about the current political system than anything Aaron Sorkin has written.

“Election” still holds up as one of the most brutally honest portrayals of high school politics on film and probably says more about the current political system than anything Aaron Sorkin has written.

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What 1999 movie is this?

  • Knowing John Malkovich
  • Seeing John Malkovich
  • Hearing John Malkovich
  • Being John Malkovich

This meta-comedy still manages to be one of the weirdest things ever shown on screens and thankfully it does it well. “Being John Malkovich” picked up three Oscar nominations that year.

This meta-comedy still manages to be one of the weirdest things ever shown on screens and thankfully it does it well. “Being John Malkovich” picked up three Oscar nominations that year.

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What 1999 movie is this?

  • Mean Machine
  • Lock, Stock and Two Smoking Barrels
  • Turn It Up
  • Snatch

This British crime comedy starring Jason Statham and Sting was one of the biggest box office draws in England in 1999, making over $20 million. It was also Statham’s first role as an actor.

This British crime comedy starring Jason Statham and Sting was one of the biggest box office draws in England in 1999, making over $20 million. It was also Statham’s first role as an actor.

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What 1999 movie is this?

  • Out of Sight
  • The Peacemaker
  • Three Kings
  • The Perfect Storm

This 1999 film takes place in 1991 during a military mission in Iraq. Perfect setting for comedy, right? Even stranger is its cast, which includes George Clooney, Mark Wahlberg and Ice Cube, taking the comedy potential through the roof.

This 1999 film takes place in 1991 during a military mission in Iraq. Perfect setting for comedy, right? Even stranger is its cast, which includes George Clooney, Mark Wahlberg and Ice Cube, taking the comedy potential through the roof.

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What 1999 movie is this?

  • Bowfinger
  • Dead Men Don’t Wear Plaid
  • The Out-of-Towners
  • Showtime

“Bowfinger” is as great as a buddy-film starring Steve Martin and Eddie Murphy can get. Martin as a Z-grade film producer and Murphy as his paranoid star really work well together in this Frank Oz directed vehicle.

“Bowfinger” is as great as a buddy-film starring Steve Martin and Eddie Murphy can get. Martin as a Z-grade film producer and Murphy as his paranoid star really work well together in this Frank Oz directed vehicle.

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What 1999 movie is this?

  • The Bone Collector
  • Playing By Heart
  • Drop Dead Gorgeous
  • Girl, Interrupted

Completely dominating the sad girl must-watch list, “Girl, Interrupted” earned Angelina Jolie an Oscar and blessed us all with her cringe-worthy acceptance speech where she confessed her incredible love for her brother.

Completely dominating the sad girl must-watch list, “Girl, Interrupted” earned Angelina Jolie an Oscar and blessed us all with her cringe-worthy acceptance speech where she confessed her incredible love for her brother.

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What 1999 movie is this?

  • Pokémon Forever
  • Space Jam
  • Pokémon: The First Movie
  • Dragon Ball Z: The Movie

It’s hard to remember how big of an event this movie was for all ‘90s kids. The Pokémon movie premiered on a Wednesday, which led to so many kids blowing off school that a new illness was coined, “the Pokéflu.”

It’s hard to remember how big of an event this movie was for all ‘90s kids. The Pokémon movie premiered on a Wednesday, which led to so many kids blowing off school that a new illness was coined, “the Pokéflu.”

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What 1999 movie is this?

  • October Sky
  • Home Grown
  • Lovely and Amazing
  • Highway

“October Sky” was a great Jake Gyllenahaal vehicle and a total tear-jerker, but now it comes across as a movie made for substitute teachers to show in class when there isn’t any work to do.

“October Sky” was a great Jake Gyllenahaal vehicle and a total tear-jerker, but now it comes across as a movie made for substitute teachers to show in class when there isn’t any work to do.

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What 1999 movie is this?

  • Bringing Out the Dead
  • Kiss of Death
  • Snake Eyes
  • Deadfall

Any Nicolas Cage movie is gonna have its ups and downs. In this one, he plays an ambulance driver in the mean streets of New York. It was also the last movie to ever be sold on LaserDisc.

Any Nicolas Cage movie is gonna have its ups and downs. In this one, he plays an ambulance driver in the mean streets of New York. It was also the last movie to ever be sold on LaserDisc.

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What 1999 movie is this?

  • Encino Man
  • Mission: Impossible
  • The Mummy
  • Journey to the Center of the Earth

“The Mummy” was the successful first installation of the franchise that has continued much longer than it needed to. Brendan Fraser plays a dumbed-down Indiana Jones type, which is enough fun for just about one feature length film.

“The Mummy” was the successful first installation of the franchise that has continued much longer than it needed to. Brendan Fraser plays a dumbed-down Indiana Jones type, which is enough fun for just about one feature length film.

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What 1999 movie is this?

  • Tales from the Hood
  • Ghost Dog: The Way of the Samurai
  • Cradle 2 the Grave
  • Boyz N the Hood

The most memorable aspect of “Ghost Dog” is the score, written by Wu-Tang Clan’s RZA. The rest of the movie was a little too weird to get mainstream attention, but its cool factor still holds up.

The most memorable aspect of “Ghost Dog” is the score, written by Wu-Tang Clan’s RZA. The rest of the movie was a little too weird to get mainstream attention, but its cool factor still holds up.

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What 1999 movie is this?

  • It’s Pat
  • The Ladies Man
  • A Night at the Roxbury
  • Superstar

Perhaps the only good movie made from a “Saturday Night Live” character, Molly Shannon totally rocked it in “Superstar.” Why hasn’t she led any major films since?

Perhaps the only good movie made from a “Saturday Night Live” character, Molly Shannon totally rocked it in “Superstar.” Why hasn’t she led any major films since?

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What 1999 movie is this?

  • Deconstructing Harry
  • Analyze This
  • America’s Sweethearts
  • My Giant

“Analyze This” is an absolutely forgettable moment in Robert De Niro’s career. He’s usually got pretty good comedic timing, but when he’s playing opposite Billy Crystal, he is just not that funny.

“Analyze This” is an absolutely forgettable moment in Robert De Niro’s career. He’s usually got pretty good comedic timing, but when he’s playing opposite Billy Crystal, he is just not that funny.

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What 1999 movie is this?

  • Cast Away
  • The Green Mile
  • Se7en
  • Armageddon

"The Green Mile" was an epic, which might be best exemplified by the fact that the movie required two VHS tapes to view (remember that problem?). Michael Clark Duncan earned an Oscar nom for his role, which included a scene where hundreds of bees fly out of his mouth.

"The Green Mile" was an epic, which might be best exemplified by the fact that the movie required two VHS tapes to view (remember that problem?). Michael Clark Duncan earned an Oscar nom for his role, which included a scene where hundreds of bees fly out of his mouth.

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What 1999 movie is this?

  • Remember The Titans
  • Any Given Sunday
  • Varsity Blues
  • Draft Day

“Varsity Blues” has all of the tropes of any good football movie: a tragic injury, a funny linebacker for comic relief, and a dramatic lead up to the ‘big game.’ What more could you ask for?

“Varsity Blues” has all of the tropes of any good football movie: a tragic injury, a funny linebacker for comic relief, and a dramatic lead up to the ‘big game.’ What more could you ask for?

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What 1999 movie is this?

  • Practical Magic
  • Dark Angel
  • The Craft
  • Dogma

“Dogma” was Kevin Smith’s comedic answer to genre shows like “Buffy the Vampire Slayer” and “Charmed” and it had some solid casting decisions. Alanis Morissette plays God, that’s all you need to know.

“Dogma” was Kevin Smith’s comedic answer to genre shows like “Buffy the Vampire Slayer” and “Charmed” and it had some solid casting decisions. Alanis Morissette plays God, that’s all you need to know.

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What 1999 movie is this?

  • Sugar & Spice
  • Jawbreaker
  • Drop Dead Gorgeous
  • Bring It On

“Jawbreaker” is basically just “Heathers” in the ‘90s, and we’re not mad about that. What is unsettling is Marilyn Manson’s cameo in the movie, which only happened because he was engaged to star Rose McGowan at the time.

“Jawbreaker” is basically just “Heathers” in the ‘90s, and we’re not mad about that. What is unsettling is Marilyn Manson’s cameo in the movie, which only happened because he was engaged to star Rose McGowan at the time.

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What 1999 movie is this?

  • Dune
  • Lost Highway
  • The Straight Story
  • Rabbits

After “Twin Peaks” and before “Mulholland Drive” David Lynch directed the G-rated and Disney-produced “The Straight Story.” It’s a totally tame tear-jerker based on the story of a man who takes a 240-mile drive on a lawn mower to meet his estranged brother.

After “Twin Peaks” and before “Mulholland Drive” David Lynch directed the G-rated and Disney-produced “The Straight Story.” It’s a totally tame tear-jerker based on the story of a man who takes a 240-mile drive on a lawn mower to meet his estranged brother.

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