98 2000s Pop Culture Trivia Questions (Ranked From Easiest to Hardest) (2024)

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98 2000s Pop Culture Trivia Questions Ranked From Easiest to Hardest (Updated For 2024)

  1. The 2004 documentary "Super Size Me" chronicled the decline in health of filmmaker Morgan Spurlock as he spent 30 days eating food exclusively from which fast food chain?

    Answer: McDonald's

  2. In 2000, who starred in the live-action remake of “How the Grinch Stole Christmas?” (Hint: Oddly, not the first time he had a green face in a film!)

    Answer: Jim Carrey

  3. Founded by an Australian surfer in California who longed for the soft sheepskin boots of his youth, what American boot brand took off in 2003 after being featured as one of Oprah's "favorite things"?

    Answer: Ugg

  4. What controversial music icon made headlines in 2002 when he dangled his nine-month-old son "Blanket" over the balcony of a German hotel to greet a crowd of onlookers?

    Answer: Michael Jackson

  5. “50 First Dates,” “Hitch,” and “The Fifth Element” were among the first films that were released on what new colorfully-named disc format on June 20, 2006?

    Answer: Blu-ray

  6. Reflecting the artist's real name, "The Marshall Mathers EP," which features songs like "Stan" and "Kim," is a 2000 studio album by what one-named rap star?

    Answer: Eminem

  7. 2003 was when Beyoncé Knowles become simply Beyoncé. That was the year she released her first solo album, “Dangerously In Love,” after splitting from which girl group that ruled the ‘90s?

    Answer: Destiny's Child

  8. Michael C. Hall is probably best known for playing the titular serial killer on what Showtime drama that ran from 2006 to 2013?

    Answer: Dexter

  9. What Will Wright created video game series released in 2000 (with sequels in 2004, 2009, and 2014) saw players watching and directing characters to mundane things like eating, sleeping, and cleaning their houses?

    Answer: The Sims

  10. E.L. James's erotic "Fifty Shades of Grey" was originally created as fan fiction for what book/movie series about vampires?

    Answer: Twilight

  11. Everyone was friends with Tom on what groundbreaking website, the most widely used social media site from 2005 to 2009, went live on August 1, 2003?

    Answer: MySpace

  12. "Don't Cha" and "Stickwitu" were 2000s hits from what "feline" girl group fronted by Nicole Scherzinger?

    Answer: The puss*cat Dolls

  13. What actress won an Best Actress Academy Award (for "The Blind Side") in 2010, the same year she won a Golden Raspberry (Razzie) award for Worst Actress (for "All About Steve")?

    Answer: Sandra Bullock

  14. Which celebrity/socialite admitted that her early 2000s catchphrase—“that’s hot”—was a favorite of her sister Nicky’s, but she ran with it and eventually trademarked it?

    Answer: Paris Hilton

  15. Sure, it was a far cry from “Ella Enchanted” and “The Princess Diaries,” but which actor shocked the Internet when she revealed that she was barely in the top 10 choices of actresses to play Andy in 2006’s “The Devil Wears Prada?”

    Answer: Anne Hathaway

  16. In 2002, Justin Guarini finished in second place to what future superstar in the inaugural season of American Idol?

    Answer: Kelly Clarkson

  17. In the year 2000, Kentwood, Louisiana opened a museum dedicated to which 18-year-old songstress who, along with her siblings Bryan and Jamie Lynn, calls the town home?

    Answer: Britney Spears

  18. In the early 2000s, you probably sported what piece of jelly jewelry on your forearm (specifically, a yellow one that said “Livestrong”)?

    Answer: Bracelet

  19. Featuring Christoper Mintz-Plasse as “McLovin,’” what 2007 nerdy teen comedy starred Jonah Hill, Michael Cera, and Emma Stone?

    Answer: Superbad

  20. What 2000 novel by Meg Cabot, adapted into a film starring Anne Hathaway, introduced the world to Mia Thermopolis, a NYC teen who discovers she's actually a royal of the fictional country of Genovia?

    Answer: The Princess Diaries

  21. Years before she starred in “Big Little Lies” with his daughter, which actress was engaged to Lenny Kravitz in 2002? (Hint: She’s now married to Keith Urban and famously divorced from Tom Cruise)

    Answer: Nicole Kidman

  22. A little birdie told us that Noah Glass, Biz Stone, and Evan Williams were three of the four founders of what social network that launched in 2006?

    Answer: Twitter

  23. Flaunt Your Fashion is a 2022 video game whose characters are based on what brand of dolls that debuted in 2001 and instantly became known for their pouty-lipped faces?

    Answer: Bratz

  24. The American version of the show "The Office" premiered on NBC in 2005. The show takes place in which Pennsylvania city?

    Answer: Scranton

  25. "The Last One" was the simple name of the final episode of what TV series, which ended its 10 and final season in 2004?

    Answer: Friends

  26. Nathalia Ramos, Skyler Shaye, Logan Browning, and Janel Parrish starred in a 2007 film based on what line of "fashion-forward" kids' dolls?

    Answer: Bratz

  27. What is the somewhat-logical term for the internet prank and meme in which an unexpected appearance of the music video for the 1987 Rick Astley song "Never Gonna Give You Up" is "planted" into an unrelated link? The meme's popularity dates back to 2008.

    Answer: Rickrolling

  28. One of the biggest hits of 2003, "Bring Me to Life" was recorded by what rock band whose name is a synonym for "impermanence?"

    Answer: Evanescence

  29. The songs "Hey Mama" by the Black Eyed Peas, "Technologic" by Daft Punk, and "Vertigo" by U2 appear in a series of commercials featuring black silhouettes dancing in front of brightly coloured backgrounds. What product, released in 2001, were these commercials created to advertise?

    Answer: iPod

  30. Released in 2005, “PCD” was the debut album of which girl group? “Don’t Cha” know the answer?

    Answer: The puss*cat Dolls

  31. Who won the Academy Award for Best Supporting Actor in 2009 just over a year after his death, becoming just the second person to win a posthumous acting Oscar?

    Answer: Heath Ledger

  32. David Brent was played by Ricky Gervais in the 2001-2003 British version of an iconic mockumentary TV series, but who played his counterpart Michael Scott in the 2005-2013 American version?

    Answer: Steve Carell

  33. In 2006, which star hot off “Mean Girls” starred in a rom-com called “Just My Luck” with Chris Pine?

    Answer: Lindsay Lohan

  34. The U.S. version of "The Office" starred Steve Carrell as the central character, Michael Scott. Who played the boorish boss in the original British version of the show?

    Answer: Ricky Gervais

  35. It could happen if the G7 combined their military might. What iconic song of the early 2000s got its title from when, as a child, Jack White (the song's singer and writer) misheard the name of The Salvation Army?

    Answer: Seven Nation Army

  36. One of the top five television series of the 2000s according to IMDb.com, what miniseries about an army regiment in Europe during W.W.II was created by Tom Hanks and Steven Spielberg, who also acted as executive producers?

    Answer: Band of Brothers

  37. Which 2004 show starred Kirsten Bell as a teen sleuth with a planetary name?

    Answer: Veronica Mars

  38. In 2007, Earl Cole became the first winner of what reality TV show to receive all the votes in the final (a fact made even more impressive by the fact there were nine people casting votes in his season, compared to the previously standard seven)?

    Answer: Survivor

  39. In “Friends,” Ross famously lets Rachel’s name slip when he’s saying his wedding vows to his second wife. What was her first name?

    Answer: Emily

  40. In 2005, which stop-motion musical from the mind of Tim Burton starred Johnny Depp as Victor, who accidentally married a dead girl?

    Answer: Corpse Bride

  41. The AP sued street artist Shepard Fairey over his Obama poster that featured what four-letter word?

    Answer: Hope

  42. Being the source of many memes, and quite a few laughs, the 2004 movie ‘Anchorman: The Legend of Ron Burgundy’ starting Will Ferrell is primarily set in which U.S. city?

    Answer: San Diego

  43. According to Nielsen SoundScan, what rapper was the best-selling musical artist between 2000 and 2009? This artist was inducted into the Rock and Roll Hall of Fame in 2022.

    Answer: Eminem

  44. In 2005, Jamie Foxx was nominated for two Academy Awards. He didn't win for his role as Max in Collateral, but did win for his leading role in what biopic?

    Answer: Ray

  45. With an assist from Timbaland, Nelly Furtado became the first Canadian woman to top the Billboard Hot 100 in the 2000s with what 2006 P-word single that really got around to a lot of radio stations?

    Answer: Promiscuous

  46. A Walk to Remember, The Notebook, and Nights in Rodanthe were all 2000s films set in North Carolina's Outer Banks and based on best-selling novels by what writer?

    Answer: Nicholas Sparks

  47. In the 2005 remake of "Charlie and the Chocolate Factory" starring Johnny Depp, the clandestine candy creator's father worked in what occupation that may not have shared an appreciation for sweets?

    Answer: Dentist

  48. Which Disney star actually released a self-titled album a year after her 2003 pop debut “Metamorphosis” which featured hits like “So Yesterday” and “Coming Clean?”

    Answer: Hilary Duff

  49. Each year October 3rd is celebrated as a holiday by the fans of what 2004 film, since it's the day that Jonathan Bennett's character Aaron Samuels asks the protagonist what day it is?

    Answer: Mean Girls

  50. Oh, say, say, say! What band with a triple exclamatory name had a hit with 2003’s “Maps?”

    Answer: Yeah Yeah Yeahs

  51. An alien race arrives on Earth and is exiled to a slum in Johannesburg, South Africa in what critically acclaimed 2009 film?

    Answer: District 9

  52. What annual event, held each year on a popular island off the coast of Los Angeles, actually began as a fictional event in the 2008 comedy Step Brothers?

    Answer: Catalina Wine Mixer

  53. Which 2009 adult animated comedy starred H. Jon Benjamin as a self-centered and self-serving secret agent with the International Secret Intelligence Service?

    Answer: Archer

  54. Worn regularly by Paris Hilton in the 2000s, the fashion brand Juicy Couture is best known for producing what rhinestoned, velour, two-piece outfits?

    Answer: Tracksuits

  55. Marion Cotillard became the first to win a Best Actress award for a non-English language film since Sophia Loren when she portrayed what chanteuse in 2007?

    Answer: Edith Piaf

  56. Before creating the hit Netflix show Orange is the New Black, Jenji Kohan created what Showtime series, which was set in the conservative suburb of Agrestic, California, and premiered in 2005?

    Answer: Weeds

  57. Mr A-Z is the (quite appropriate) name of a 2005 album by what Virginian singer-songwriter behind hits like "The Remedy?"

    Answer: Jason Mraz

  58. What pop hit by the duo of Cee Lo Green and Danger Mouse (known by the name Gnarls Barkley) was named by Rolling Stone magazine to be the best song of the 2000s?

    Answer: Crazy

  59. What popular publication targeted at teenage girls and young women was first published in 2003 as a "sister publication" to a well-known magazine?

    Answer: Teen Vogue

  60. Nike co-founder Phil Knight's son Travis was a lead animator for a 2009 film that was nominated by the Visual Effects Society for best "Character Animation in a Feature Production." What was the name of this stop-motion animated fantasy film based on a 2002 novel by Neil Gaiman?

    Answer: Coraline

  61. The subject of many recent internet memes, a 2007 episode of what Nickelodeon teen sitcom features the two title characters trapped in a newly-built treehouse after forgetting to cut out a doorway?

    Answer: Drake & Josh

  62. French actress Audrey Tautou is perhaps best known in the United States for playing what whimsical waitress in a namesake 2001 film?

    Answer: Amelie

  63. Although she's since been surpassed by Drake and Taylor Swift, what artist's 2005 single "Hung Up" gave her a 36th top ten US hit, then the most of all time?

    Answer: Madonna

  64. Which 2008 sci-fi thriller starred Hayden Christiansen as David Rice, a teenager who figures out he can teleport after falling through the ice, then takes his abilities on the road to rob banks and travel the world (that is, until he’s tracked down by some people who are not too pleased with his unique skill)?

    Answer: Jumper

  65. What early 2010’s collectible rubber bracelets that formed into shapes (typically animals) became such a cultural phenomenon that national news outlets reported the toys being banned in school districts?

    Answer: Silly Bandz

  66. Sometimes abbreviated as ATHF, what Adult Swim cartoon revolved around the adventures of Master Shake, Frylock, and Meatwad?

    Answer: Aqua Teen Hunger Force

  67. A short-lived animated TV show based on what 1994 cult classic film featured the voices of actors Jeff Anderson, Jason Mewes, and Kevin Smith (although, for character reasons, not as frequently) reprising their original roles?

    Answer: Clerks

  68. Songwriters Hayley Williams and Josh Farro were added as writers on Olivia Rodrigo's song "Good 4 U," after listeners pointed out the similarities between the song and what band's 2007 hit "Misery Business?"

    Answer: Paramore

  69. Created and written by former police detective David Simon, the HBO crime drama "The Wire" is mainly set in what East Coast city?

    Answer: Baltimore, Maryland

  70. "A History of Violence" (2006) was the last Hollywood movie to be released in what format? It dates back to 1976.

    Answer: VHS

  71. In the early 2000s, trucker hats were all the rage, worn by celebs like Britney Spears, Paris Hilton, Justin Timberlake, and Ashton Kutcher. Which Los Angeles brand, not founded in Germany or the Netherlands like you might guess, popularized this trend?

    Answer: Von Dutch

  72. Released in 2002, “Stripped” is the fourth studio album of which New Yorker whose father was born in Ecuador?

    Answer: Christina Aguilera

  73. What "Coal Miner's Daughter," then 72 years old, released the critically applauded album Van Lear Rose in 2004 in collaboration with Jack White?

    Answer: Loretta Lynn

  74. Though he also released albums like the Black Album and Kingdom Come in the 2000s, from 2001 to 2009, iconic rapper Jay-Z released three sequentially numbered albums all featuring what title?

    Answer: The Blueprint

  75. What word, describing a channel for creativity and communication arising out of the Internet age, was Merriam-Webster's top Word of the Year in 2004?

    Answer: Blog

  76. The iPod, launched in 2001, was named by freelance copywriter Vinnie Chieco, based on images from what movie?

    Answer: 2001: A Space Odyssey

  77. What 2001 film from Japan's Studio Ghibli (which was distributed in North America by Disney in 2002) won the Academy Award for Best Animated Feature in 2003?

    Answer: Spirited Away

  78. In 2003, actor and Miami Heat dancer Trista Rehn became the first person to appear on American television under what titular role?

    Answer: The Bachelorette

  79. You might say author James Frey "fell apart" when he admitted on the Oprah Winfrey Show in 2006 that he had largely made up what bestselling memoir?

    Answer: A Million Little Pieces

  80. "The Angry American" is the subtitle of what aggressively patriotic song that provided Toby Keith his first and only Billboard hit in 2002?

    Answer: Courtesy of the Red, White, and Blue

  81. Made of chenille and equipped with transformative velcro straps, what toys--or decorative home goods, depending on how you look at it--were invented by entrepreneur Jennifer Telfer in 2003?

    Answer: Pillow Pets

  82. "Would you love me if I was down and out?" is just one of the titular things being asked by 50 Cent, J.Period, and Nate Dogg in what hit song from 2003?

    Answer: 21 Questions

  83. The last episode of series Friends went to air in 2004. The character Chandler had the last line of the series at the end of the episode which was only one word. What was that word?

    Answer: Where

  84. In “Spirit: Stallion of the Cimarron (2002)”—an animated adventure by DreamWorks and an emotional soundtrack featuring Bryan Adams— which actor can be heard as the inner voice of the film’s star horse?

    Answer: Matt Damon

  85. According to IMDB's ratings, the five best movies of the released between 2001 and 2010 were all directed by one of two directors. Three of them are the Lord of the Rings Trilogy, directed by Peter Jackson, but who directed the other two top rated movies of this time period?

    Answer: Christopher Nolan

  86. Fountains of Wayne frontman Adam Schlesinger wrote several of the songs featured in what 2001 film, which was loosely based on both an Archie Comics series and a Hanna-Barbera cartoon?

    Answer: Josie and the puss*cats

  87. Jennifer Lopez's choice to wear a low-cut green Versace dress to the 2000 Grammy Award ceremony and the attention it recieved prompted the introduction of which specific search engine a year later?

    Answer: Google Image Search

  88. In 2002, which 3D game in the Nintendo Super Mario franchise was released for GameCube and took players on an adventure around Isle Delfino?

    Answer: Super Mario Sunshine

  89. In 2009, which single from Rob Thomas starts out with “Oh what the hell, she says, I just can’t win for losing?” (Hint: The song’s title refers to her tears which fall like a precious gem on the floor…)

    Answer: Her Diamonds

  90. !n 2005, the enigmatic artist Banksy placed a piece of concrete with a picture of a prehistoric man pushing a shopping cart into what prestigious museum? Although the first time was a hoax (which took museum staff three days to notice), the piece went back on display for an exhibition in 2018.

    Answer: British Museum

  91. In 2002, the UK Patent Office ruled against the Metropolitan Police in regard to their objection to the BBC’s trademark claim for an object in the television show Doctor Who. What is the name of the thing the BBC was trying to trademark?

    Answer: TARDIS

  92. Although it was rumored that there were personal feelings involved, which music star was quoted as saying Madonna’s song for the 2002 movie ‘Die Another Day’ was the “worst James Bond song ever”?

    Answer: Elton John

  93. Catapulting both Paris Hilton and Nicole Richie to stardom, the first season of the TV series ‘The Simple Life’ was filmed in which U.S. state?

    Answer: Arkansas

  94. Glamping, manspreading, and fro-yo were all added to the Oxford English Dictionary in 2016. Joining them was a word that defines a particular style of online writing grouping things together. Love them or hate them, we know you've clicked on them. What is this portmanteau word?

    Answer: Listicle

  95. In the Austin Powers movie "Goldmember," released in 2002, the title character is from which European country?

    Answer: Netherlands

  96. In 2007, a number of mysterious blinking electronic signs caused multiple bomb scares in the Boston area. The signs, meant as a guerilla marketing tactic, depicted the Mooninites from what Adult Swim cartoon?

    Answer: Aqua Teen Hunger Force

  97. From a Basem*nt on the Hill was the last album recorded by what influential Portland singer-songwriter, who died before its 2004 release?

    Answer: Elliott Smith

  98. Bill Gates appears on the cover of a May 2005 issue of Time Magazine. He is holding something in his hand, and the subtitle reads: "Microsoft has finally made something hip." What is Gates holding? Circle back to this question later if you can't think of it right now...

    Answer: Xbox 360

What makes 2000s pop culture trivia so engaging?

For starters, the 2000s were a decade full of famous firsts.

It was the first decade of the new millennium, and it saw a lot of technological advances.

From the launch of the first iPod to the rise of social media, the 2000s were a time of change.

And that's reflected in the pop culture of the time.

The 2000s were also a decade of huge pop culture moments.

Just off the top of our heads, we can think of dozens more pop culture trivia questions, but we'll save those for another time.

How can you create the perfect 2000s pop culture trivia quiz?

Using Water Cooler Trivia, you can receive a new trivia quiz every week, straight to your inbox.

You can also customize the quizzes to fit your group's interests.

For example, if you want a quiz that's all about 2000s pop culture, we can make that happen.

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98 2000s Pop Culture Trivia Questions (Ranked From Easiest to Hardest) (1)

About the Author

Eli Robinson is the Chief Trivia Officer at Water Cooler Trivia. He was once in a Bruce Springsteen cover band called F Street Band.

98 2000s Pop Culture Trivia Questions (Ranked From Easiest to Hardest) (2024)
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