Can You Name These Movies That Are 20 Years Old in 2020?

By: Jane Andrews
Estimated Completion Time
4 min
Can You Name These Movies That Are 20 Years Old in 2020?
Image: Scott Free Productions/ Red Wagon Entertainment[1]

About This Quiz

In the year 2000 (channel your best Conan O'Brien impression here), there was a brand spanking new century in front of us. As we bid the '90s a fond farewell and welcomed the start of the new millennium, we reveled in Nokia flip phones, AOL messenger, Madonna's "Music" and more. "The Sopranos" and "Sex and the City" were our premium-TV obsessions (remember the slogan "It's not TV. It's HBO"?), while sitcoms like "Friends" and "Frasier" ruled the primetime airwaves. And when it came to movies, we actually had to go to the theater to see one. In this era before the dawn of streaming services, the closest thing we had to on-demand entertainment was a trip to the nearest Blockbuster Video.

One warning about this quiz — it may make you feel a little old. It's hard to believe that the turn of the century was 20 years ago and that these movies have been a part of American pop culture for two decades. From silly cult comedies like "Bring It On" and "Dude, Where's My Car?" to Oscar contenders such as "Gladiator" and "Cast Away," 2000 was a memorable year for movies. 

How well do you remember the fine films (and famous flops) that entertained audiences during this year? Take our quiz and show us what you know!

8. miss
Castle Rock Entertainment/ Village Roadshow Pictures/ NPV Entertainment/ Fortis Films
Can you name this popular Sandra Bullock comedy?
"While You Were Sleeping"
"Miss Congeniality"
"Two Weeks Notice"
"Practical Magic"
Correct Answer
Wrong Answer

Released on December 22, 2000, this hit movie earned a box office gross of $213 million worldwide. Its sequel, "Miss Congeniality 2: Armed and Fabulous," also starring Sandra Bullock, came out in 2005.

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9. gladiator
Scott Free Productions/ Red Wagon Entertainment[1]
What's the name of this Oscar-winning drama?
"Apocalypto"
"Gladiator"
"The Knights of the Quest"
"King Arthur"
Correct Answer
Wrong Answer

The second-highest-grossing film of 2000, "Gladiator," won five Academy Awards, including Best Picture and Best Actor (Russell Crowe). It also won Golden Globes for Best Motion Picture — Drama and Best Original Score — Motion Picture.

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1. cast away
ImageMovers/ Playtone
Do you recognize this popular Tom Hanks film?
"You've Got Mail"
"Big"
"Forrest Gump"
"Cast Away"
Correct Answer
Wrong Answer

Released on December 22, 2000, "Cast Away" was a hit with both critics and the box office. Tom Hanks earned an Oscar nomination and a Golden Globe win for his portrayal of stranded FedEx employee Chuck Noland.

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35. obrothers
Touchstone Pictures[1]/ Universal Pictures[1]/ StudioCanal[1]/ Working Title Films[2]/ Blind Bard Pictures[3]
Do you recognize this George Clooney movie?
"One Fine Day"
"Three Kings"
"O Brother, Where Art Thou?"
"Intolerable Cruelty"
Correct Answer
Wrong Answer

George Clooney won a Golden Globe Award for Best Motion Picture — Musical or Comedy for his role in this Coen brothers crime comedy. The movie also received Oscar nominations for Best Adapted Screenplay and Best Cinematography.

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5. erin
Universal Pictures/ Columbia Pictures/ Jersey Films
Can you tell us the name of this Steven Soderbergh film?
"Sex, Lies, and Videotape"
"Erin Brockovich"
"Full Frontal"
"Traffic"
Correct Answer
Wrong Answer

Julia Roberts won an Academy Award for Best Actress for her portrayal of Erin Brockovich in this film, which is based on a true story. The movie also earned nominations for Best Picture, Best Director (Soderbergh), Best Supporting Actor (Albert Finney) and Best Original Screenplay.

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4. american
Columbia Pictures/ Edward R. Pressman Productions/ Muse Productions
What about this creepy thriller — do you recognize it?
"American Psycho"
"The Skulls"
"Lost Souls"
"What Lies Beneath"
Correct Answer
Wrong Answer

Starring Christian Bale as a psychopathic serial killer, "American Psycho" is based on a Bret Easton Ellis novel of the same name. The movie also features appearances by Willem Dafoe, Jared Leto, Chloë Sevigny and Reese Witherspoon.

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37. perfectstorm
Baltimore Pictures/ Radiant Productions
What's the name of this disaster drama?
"The Perfect Storm"
"Armageddon"
"Deep Impact"
"Jaws"
Correct Answer
Wrong Answer

Based on the 1997 non-fiction book of the same name, this movie about a commercial fishing vessel lost at sea stars George Clooney, Mark Wahlberg, Diane Lane and John C. Reilly. It was a box office hit, earning more than $328 million worldwide.

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33. beach
20th Century Fox
Can you identify this movie, starring Leonardo DiCaprio?
"The Beach"
"Titanic"
"Wolves of Wall Street"
"Inception"
Correct Answer
Wrong Answer

Based on a 1996 novel of the same name, this adventure-drama movie was filmed on location in Thailand, on the island of Ko Phi Phi Le. While a modest box office success, it received mostly negative reviews from critics.

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13. family man
Beacon Pictures/ Saturn Films
What's the name of this romantic comedy-drama?
"Bad Santa"
"The Holiday"
"The Family Man"
"It's a Wonderful Life"
Correct Answer
Wrong Answer

This holiday-themed film with a supernatural spin stars Nicolas Cage, Téa Leoni and Don Cheadle. It tells the story of a bachelor who wakes up one morning to find himself with a very different life.

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26. myselfandirene
Conundrum Entertainment
Jim Carrey starred in this raucous comedy. What's it called?
"Me, Myself & Irene"
"There's Something About Mary"
"Nurse Betty"
"Road Trip"
Correct Answer
Wrong Answer

Directed by the Farrelly brothers, "Me, Myself & Irene" received mixed reviews from critics but was a box office hit. It earned $24.2 million in its opening weekend in the U.S. and a gross of more than $149 million in total worldwide.

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15. chocolat
Miramax Films
What's the name of this delicious romantic comedy?
"Cupcake"
"Chocolat"
"The Bakery"
"The Chocolate House"
Correct Answer
Wrong Answer

Starring Juliette Binoche, Judi Dench, Alfred Molina and Johnny Depp, "Chocolat" was nominated for five Academy Awards, including Best Picture. It lost to the Russell Crowe movie "Gladiator."

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11. What Lies Beneath
ImageMovers
Can you identify this frightening film?
"Memento"
"Hollow Man"
"Enigma"
"What Lies Beneath"
Correct Answer
Wrong Answer

Directed by Robert Zemeckis, this supernatural chiller stars Harrison Ford and Michelle Pfeiffer. A box office hit, it earned more than $291 million worldwide and became the tenth-highest-grossing film of 2000.

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21. destination
Zide/Perry Productions/ Hard Eight Pictures
A bunch of teens were in a lot of trouble in this creepy flick. Which one is it?
"Final Destination"
"Book of Shadows: Blair Witch 2"
"Scream 3"
"Terror Tract"
Correct Answer
Wrong Answer

The first of five movies, "Final Destination" is about people who cheat death, only to die in creepier, more complex ways. In early 2019, New Line announced it was working on a reboot of the successful film franchise.

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32. bigmomma
20th Century Fox[1]/ Regency Enterprises[1]
Do you remember this larger-than-life comedy?
"Blue Streak"
"Black Knight"
"Big Momma's House"
"Big Momma's House 2"
Correct Answer
Wrong Answer

Martin Lawrence stars in this funny film which was panned by critics but a big hit with audiences. It spawned two sequels: "Big Momma's House 2" and "Big Mommas: Like Father, Like Son."

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2. charlie
Columbia Pictures/ Leonard Goldberg Productions/ Flower Films/ Tall Trees Productions
What's the name of this action-packed movie?
"Charlie's Angels"
"Charlie's Angels: Full Throttle"
"Crouching Tiger, Hidden Dragon"
"The Matrix"
Correct Answer
Wrong Answer

This revamp of the popular 1970s TV show "Charlie's Angels" stars Drew Barrymore, Cameron Diaz, Lucy Liu and Bill Murray. It earned more than $259 million worldwide at the box office and was followed by a sequel in 2003.

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19. scary movie
Wayans Bros. Entertainment[1]/ Gold/Miller Productions[1]/ Brad Grey Pictures[1]
What's this horror movie spoof called?
"Scream"
"Scared Straight"
"Scary Movie"
"Shriek If You Know What I Did Last Friday the Thirteenth"
Correct Answer
Wrong Answer

A parody of popular horror flicks like "Scream" and "I Know What You Did Last Summer," "Scary Movie" spawned four sequels of its own. Anna Faris stars in all but the fifth installment.

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18. xman
Marvel Entertainment Group/ The Donners' Company/ Bad Hat Harry Productions
Do you recognize this Marvel movie?
"X-Men"
"X2"
"The Wolverine"
"Logan"
Correct Answer
Wrong Answer

"X-Men," which inspired multiple sequels, prequels and spin-offs, was popular with critics and audiences. The movie features an ensemble cast, including Hugh Jackman, Halle Berry, Ian McKellen and Patrick Stewart.

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14. best in
Castle Rock Entertainment
Do you know the name of this hilarious mockumentary?
"Best in Show"
"Waiting for Guffman"
"This Is Spinal Tap"
"A Mighty Wind"
Correct Answer
Wrong Answer

Directed by Christopher Guest, this film focuses on contestants participating in a prestigious dog show. It features frequent Guest collaborators, including Catherine O'Hara, Eugene Levy, Michael McKean and Parker Posey.

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3. bringiton
Beacon Pictures
How about this cult classic cheerleading film — what's it called?
"Fired Up"
"Pom-Pom Girls"
"Bring It On"
"Bring It Down"
Correct Answer
Wrong Answer

Starring Kirsten Dunst and Eliza Dushku, this surprise hit became a film franchise, spawning five direct-to-video sequels, none of which feature the original cast. A stage musical was also produced in 2011.

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25. wheresmycar
Alcon Entertainment (uncredited)
Do you know the name of this Ashton Kutcher comedy?
"Dazed and Confused"
"Friday"
"Dude, Where's My Car?"
"Pineapple Express"
Correct Answer
Wrong Answer

Jennifer Garner makes an early film appearance in this flick as Wanda, the girlfriend of Ashton Kutcher's character, Jesse. The movie, which did well at the box office but was disliked by critics, also stars Seann William Scott.

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20. almost
Columbia Pictures/ DreamWorks Pictures/ Vinyl Films
Can you tell us the name of this Cameron Crowe classic?
"Say Anything"
"Almost Famous"
"Jerry Maguire"
"Vanilla Sky"
Correct Answer
Wrong Answer

Kate Hudson earned an Academy Award nomination for Best Actress in a Supporting Role for her breakout performance as band promoter Penny Lane in this film. The movie won one Oscar, for Best Original Screenplay.

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31. ladiesman
SNL Studios
This comedy is based on a character from "Saturday Night Live." What's it called?
"The Ladies Man"
"Superstar"
"Coneheads"
"It's Pat"
Correct Answer
Wrong Answer

Starring "Saturday Night Live" cast member Tim Meadows, "The Ladies Man" follows the misadventures of Leon Phelps, the Courvoisier-loving radio host created by Meadows for the sketch comedy show. It was not well received, unfortunately.

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39. dream
Thousand Words/ Protozoa Pictures
Do you know what movie this shot is from?
"Requiem for a Dream"
"Black Swan"
"Mother!"
"Pi"
Correct Answer
Wrong Answer

This heavy psychological drama about drug addiction stars Jared Leto, Jennifer Connelly, Marlon Wayans and Ellen Burstyn. Burstyn received an Academy Award nomination for Best Actress for her performance.

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24. battle
Morgan Creek Productions/ Franchise Pictures[1]
This sci-fi film was a big disappointment at the box office. Do you know it?
"Battlefield Earth"
"2001"
"Leviathan"
"Land of the Giants"
Correct Answer
Wrong Answer

"Battlefield Earth" was also referred to as "Battlefield Earth: A Saga of the Year 3000." John Travolta stars in this movie based on an L. Ron Hubbard novel. The box office dud was panned by critics and has been called one of the worst movies ever made by entertainment magazines and websites.

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27. 9yard
Morgan Creek Productions/ Franchise Pictures/ Rational Packaging/ Lansdown Films
This hit comedy spawned a less-successful sequel in 2004. Which 2000 movie is it?
"Hanging Up"
"Meet the Parents"
"The Whole Ten Yards "
"The Whole Nine Yards"
Correct Answer
Wrong Answer

"The Whole Nine Yards" stars Bruce Willis and Matthew Perry. Because the two actors got along so well during the making of the movie, Willis agreed to appear in a three-episode guest-starring role on "Friends."

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12. highf
Touchstone Pictures/ Working Title Films/ Dogstar Films/ New Crime Productions
This movie is based on a Nick Hornby novel. What's it called?
"About a Boy"
"High Fidelity"
"Fever Pitch"
"A Long Way Down"
Correct Answer
Wrong Answer

Starring John Cusack and Jack Black, "High Fidelity" was a critical and box office hit when it was released. It's currently being adapted into a television show, set to debut on Hulu in early 2020.

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17. payitforward
Bel-Air Entertainment/ Tapestry Films/ Pathé
Can you tell us the name of this movie starring Haley Joel Osment and Helen Hunt ?
"As Good As It Gets"
"Pay It Forward"
"The Sixth Sense"
"A.I. Artificial Intelligence"
Correct Answer
Wrong Answer

This drama also features an appearance by rocker Jon Bon Jovi. The movie is loosely based on a 1999 novel of the same name. While critics praised the actors for their performances, most found the story too cliche.

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10. memento
Summit Entertainment/ Team Todd
Here's a brain-bending thriller from 2000. What's it called?
"Memento"
"Memento Mori"
"Amnesia"
"Memory Loss"
Correct Answer
Wrong Answer

Directed by Christopher Nolan, who went on to make big-screen hits such as "Batman Begins," "The Dark Knight" and "Inception," "Memento" premiered at the Venice International Film Festival on September 5, 2000. It didn't hit American theaters until early 2001.

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29. duet
Hollywood Pictures
What's the name of this fun ensemble film?
"Love Actually"
"Valentine's Day"
"Karaoke Queen"
"Duets"
Correct Answer
Wrong Answer

Co-starring Gwyneth Paltrow, Paul Giamatti, Scott Speedman, Huey Lewis and more, this movie was directed by Bruce Paltrow, Gwyneth's dad. It's the only time the two worked together on a film.

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22. returntome
Metro–Goldwyn–Mayer
Actor David Duchovny of the "X-Files" stars in this film. Can you name it?
"I Want to Believe"
"Zoolander"
"Return to Me"
"Evolution"
Correct Answer
Wrong Answer

Duchovny stars alongside Minnie Driver, Bonnie Hunt, Robert Loggia and David Alan Grier in this romantic comedy-drama. The movie also features legendary actor Carroll O'Connor in his final film appearance.

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30. boiler room
Team Todd
What's the title of this Ben Affleck movie?
"Boiler Room"
"Good Will Hunting"
"Chasing Amy"
"Hollywoodland"
Correct Answer
Wrong Answer

Featuring an ensemble cast that includes Giovanni Ribisi, Vin Diesel, Nia Long and Ron Rifkin, "Boiler Room" is a crime drama about a group of young, wealthy stockbrokers with little respect for the law.

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34. you can
Paramount Classics
Do you know the name of this indie film?
"Maze"
"The Gift"
"Where the Heart Is"
"You Can Count on Me"
Correct Answer
Wrong Answer

Laura Linney earned an Oscar nomination for Best Actress for her role in this sweet family film, which also stars Matthew Broderick, a young Rory Culkin, and Mark Ruffalo in his breakout performance.

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6. How the Grinch Stole Christmas
Imagine Entertainment
What's the name of this fantastical Christmas movie?
"The Grinch"
"How the Grinch Stole Christmas"
"Getting Grinchy With It"
"A Very Grinchy Christmas"
Correct Answer
Wrong Answer

This live adaptation of the famous Dr. Seuss story stars Jim Carrey as the Grinch. The movie was a mega hit, earning more than $345 million worldwide and an Academy Award for Best Makeup and Hairstyling.

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38. pollack
Sony Pictures Classics
This movie is about a famous artist. What's it called?
"Matisse"
"Picasso"
"Chagall"
"Pollock"
Correct Answer
Wrong Answer

Marcia Gay Harden won an Academy Award for Best Supporting Actress for her performance in this bio. Ed Harris, who plays painter Jackson Pollack, received an Oscar nomination for Best Actor; however, he lost to Russell Crowe for "Gladiator."

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36. the next
Lakeshore Entertainment
Madonna stars in this comedy-drama. What's it called?
"Evita"
"Desperately Seeking Susan"
"The Next Best Thing"
"A League of Their Own"
Correct Answer
Wrong Answer

Also starring Rupert Everett and Benjamin Bratt, this movie was panned by critics and a box office dud. For her performance, Madonna won a Golden Raspberry Award for Worst Actress.

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28. pitch black
PolyGram Filmed Entertainment/ Interscope Communications/ Gramercy Pictures
Do you recognize this sci-fi action film?
"The Chronicles of Riddick"
"Pitch Black"
"Dark Fury"
"Blind Planet"
Correct Answer
Wrong Answer

"Pitch Black" is the first of three movies featuring Vin Diesel as escaped con Richard B. Riddick. The film's two sequels are "The Chronicles of Riddick," released in 2004, and "Riddick," which came out in 2013.

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40. wonderboys
BBC Films/ Curtis Hanson Productions/ Marubeni/ MFF Feature Film Productions/ Mutual Film Company/ Scott Rudin Productions/ Tele München Fernseh Produktionsgesellschaft/ Toho-Towa
Can you identify this Michael Douglas movie?
"Romancing the Stone"
"War of the Roses"
"Wonder Boys"
"Don't Say a Word"
Correct Answer
Wrong Answer

Based on a novel of the same name, this comedy-drama also stars Tobey Maguire, Frances McDormand, Katie Holmes and Robert Downey Jr. Bob Dylan won both an Oscar and a Golden Globe award for the original song he wrote for the film, "Things Have Changed."

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23. houseofmirth
Three Rivers Productions[1]/ Granada Productions[1]/ Showtime[1]
This movie features an "X-Files" star. Which movie is it?
"Little Women"
"Shakespeare in Love
"Jane Eyre"
"The House of Mirth"
Correct Answer
Wrong Answer

Based on the classic Edith Wharton novel of the same name, "The House of Mirth" stars Gillian Anderson, Laura Linney and Eric Stoltz. Anderson won a British Independent Film Award for Best Actress for her portrayal of the film's heroine, Lily Bart.

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16. mission impossible
Cruise/Wagner Productions[1]
Which Tom Cruise movie is this shot from?
"Minority Report"
"The Firm"
"Mission: Impossible"
"Mission: Impossible 2"
Correct Answer
Wrong Answer

This highly anticipated sequel to the 1996 film "Mission: Impossible" became the highest-grossing film of 2000. It earned more than $549 million worldwide and was followed by "Mission: Impossible III" in 2006.

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7. unbreakable
Touchstone Pictures/ Blinding Edge Pictures/ Barry Mendel Productions/ Limited Edition Productions Inc.
Which M. Night Shyamalan movie is this screenshot from?
"The Sixth Sense"
"Unbreakable"
"Signs"
"Split"
Correct Answer
Wrong Answer

Starring Bruce Willis and Samuel L. Jackson, this hit thriller resulted in two follow-up films that didn't come out until years later — "Split," which was released in 2016, and "Glass," which came out in 2019.

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You Got:
/40
Scott Free Productions/ Red Wagon Entertainment[1]