86 2000s Pop Culture Trivia Questions (Ranked From Easiest to Hardest)

Updated Date:
January 9, 2023
Which companies play trivia with their co-workers every week?
lyft logo
amazon logonike logoimpossible logo

Are you looking for the ultimate source of 2000s pop culture trivia questions?

From Britney Spears to Justin Timberlake, the 2000s were a decade full of iconic pop culture moments.

And what better way to relive those memories than with a trivia game?

Whether you're planning a 2000s-themed party or just want to take a trip down memory lane, our list of 2000s pop culture trivia questions is sure to give you a blast from the past.

Before we take a dive into our 2000s pop culture trivia questions and answers, we want to tell you a bit about Water Cooler Trivia.

Water Cooler Trivia is the perfect way to add some fun and friendly competition to your next gathering.

We've got a wide variety of trivia categories to choose from, including pop culture, history, sports, and more.

And best of all, we offer a four-week free trial - so you can try us out before making a commitment.

Get your friends together and see who can answer the most 2000s pop culture trivia questions correctly.

86 2000s Pop Culture Trivia Questions Ranked From Easiest to Hardest (Updated For 2023)

  1. Jack Black starred in a sports comedy film in 2006 that was loosely based on the real-life story of a Mexican Catholic priest. What was the name of this film, the alter ego of the priest when he entered the wrestling ring?

    Answer: Nacho Libre

  2. 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

  3. In 2004, what popular ABC TV show began with Jack opening his eyes on a mysterious beach, amidst a plane crash?

    Answer: Lost

  4. 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

  5. What Canadian artist released her debut studio album "Let Go" in 2002 which heavily emphasized her skate punk persona? The album's release led to critics and music publications to anoint her as the "Pop Punk Queen."

    Answer: Avril Lavigne

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

    Answer: The Pussycat Dolls

  7. Burger Beard, also known as Painty the Pirate, sings the theme song to what long-running and frequently meme-able animated TV series?

    Answer: SpongeBob SquarePants

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

    Answer: Bracelet

  9. 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

  10. What 2008 Rihanna hit, featuring Jay-Z, featured a video of Ri Ri in part dancing with the titular protective device?

    Answer: Umbrella

  11. Which 2007 nerdy teen comedy starred Jonah Hill, Michael Cera, Emma Stone, and Christoper Mintz-Plasse (as “McLovin’”)?

    Answer: Superbad

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

    Answer: Kelly Clarkson

  13. 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

  14. The 2012 song "Skyfall" was written and recorded for the James Bond film of the same name. It won an Academy Award, a Grammy Award, and a Golden Globe for Best Original Song, as well as the Brit Award for British Single of the Year. What singer co-wrote and performed the track?

    Answer: Adele

  15. 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

  16. 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

  17. T-t-t-totally dude! In 2007, Shop Boyz wanted you to Party Like a ______.

    Answer: Rock Star

  18. A Canadian actor began his acting career on the Mickey Mouse Club as a teen in 1993 and transitioned to adult stardom with the massively popular "The Notebook" in 2004 and an Academy Award nomination in 2006 for "Half Nelson." Who is this Ontarian?

    Answer: Ryan Gosling

  19. 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

  20. 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

  21. "With a taste of a poison paradise," what 2003 hit song was originally written with Janet Jackson, not Britney Spears, in mind?

    Answer: Toxic

  22. 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

  23. In 2011, an online petition was started to protest what oft-decried rock band from providing the halftime entertainment of a Thanksgiving NFL game in Detroit? More than 50,000 people signed the petition. The band's name is also a football-related term.

    Answer: Nickelback

  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. What 2000s medical TV show was set in New Jersey and included frequent allusions to the titular protagonist's similarities to Sherlock Holmes?

    Answer: House

  26. 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

  27. Sandra Bullock plays a boss who forces her assistant, played by Ryan Reynolds, to marry her so she can avoid being deported, in what 2009 rom-com?

    Answer: The Proposal

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

    Answer: Friends

  29. 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

  30. Cuauhtémoc Moctezuma Brewery has many brands of popular beer, but only one had a series of commercials that lasted more than a decade and starred Jonathan Goldsmith. Goldsmith's name-less character became iconic enough to be included in many internet memes in the 2000s. Name the beer brand OR the character.

    Answer: Dos Equis (Most Interesting Man in the World)

  31. Starring Keira Knightley and Parminder Nagra, what 2002 film tells the story of Jesminder "Jess" Bhamra, a young woman of Indian descent who defies her parents' wishes to play on a London soccer team?

    Answer: Bend It Like Beckham

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

    Answer: The Pussycat Dolls

  33. 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

  34. Meredith and Olivia are two of the cats owned by what popular singer born in 1989? The pets are named after leading ladies from Grey's Anatomy and Law & Order: SVU.

    Answer: Taylor Swift

  35. What raspy-voiced actor played counterterrorist agent Jack Bauer on the long-running Fox series "24?"

    Answer: Kiefer Sutherland

  36. 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

  37. In the film "Cast Away," Chuck Noland reaches an uninhabited island after a plane crashes into which ocean?

    Answer: The Pacific Ocean

  38. Shadow Man, Tiana, and Louis the Alligator are all characters in what 2009 animated Disney film?

    Answer: The Princess and the Frog

  39. The 2002 movie entitled "______ ______ 2: Island of Lost Dreams" stars Alexa PanaVega and Daryl Sabara as the Cortez siblings who try to save the world from a mad geneticist. The adventures of these undercover youngsters are filmed primarily in Manuel Antonio National Park in Costa Rica. What 2-word film franchise fills in the blank?

    Answer: Spy Kids

  40. 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

  41. Born in Cincinnati, brothers Nick and Drew Lachey were half of the lineup of what "hot" boy band?

    Answer: 98 Degrees

  42. Featuring her then-future husband Jay-Z, what 2003 Beyoncé single was named the greatest pop song of the 2000s by VH1?

    Answer: Crazy in Love

  43. What Disney channel comedy show was created in 2001 by Terri Minsky, and was about the personal life of a titular teenage girl who sometimes had a cartoon version of herself act out her private thoughts? It featured Robert Carradine as the girl’s father.

    Answer: Lizzie McGuire

  44. Hugh Grant was extremely reluctant to film the scene in which he boogies through 10 Downing Street to "Jump (For My Love)" in what classic 2003 Christmas movie?

    Answer: Love Actually

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

    Answer: Veronica Mars

  46. “…of a Dangerous Mind” and “…of a Teenage Drama Queen” end 2000s movie titles that start with what word that was the full title of a 2004 Usher album?

    Answer: Confessions

  47. What singer released the song “Work It Out” in 2002, as part of the “Austin Powers in Goldmember” soundtrack, a movie with which she was involved?

    Answer: Beyonce

  48. What Canadian-American "Grey's Anatomy" actress is the daughter of middle-class South Korean immigrants and currently stars in the American spy thriller series Killing Eve?

    Answer: Sandra Oh

  49. Moto Moto is an animated hippo known for his flirtatious attitude and also for an extremely popular meme of Moto Moto exiting a pond. From what movie franchise is Moto Moto from?

    Answer: Madagascar

  50. In 2000, Nine Days had a hit with “Absolutely (Story of a ______),” the lead single off their album “The Madding Crowd.” (Hint: She cried a river and drowned the whole world)

    Answer: Girl

  51. What rapper and former teen singer, of such late 90’s/early 2000’s hits as “Crush On You”, “That’s How I Beat Shaq”, and “Aaron’s Party (Come Get It)”, is planning on boxing former NBA player Lamar Odom in a June 2021 boxing exhibition match?

    Answer: Aaron Carter

  52. 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

  53. What 2000s sci-fi series starred Jennifer Garner as CIA agent Sydney Bristow, who had to hide the nature of her job from her friends and family?

    Answer: Alias

  54. The AP sued street artist Shepard Fairey over his Obama poster that featured what word?

    Answer: Hope

  55. In the 2005 remake of "Charlie and the Chocolate Factory" starring Johnny Depp, the clandestine candy creator's father worked in what occupation? Hint: some may call the occupation ironic, some may call it coincidental.

    Answer: Dentist

  56. What American TV program is based on the Swedish reality show "Expedition Robinson"?

    Answer: Survivor

  57. "______ Allocation Load-Lifter: Earth-class" is technically the name of a beloved movie character from a 2008 film revolving around environmental, romantic, and technological themes. What word is missing from the blank?

    Answer: Waste

  58. Originally airing on Bravo, which reality show pairs up rich, millionaire singles on dates and ran from 2008 to 2015?

    Answer: The Millionaire Matchmaker

  59. What 2004 movie starred Nicolas Cage as Benjamin Franklin Gates, a historian searching for a vast stockpile of artifacts hidden by American Freemasons during the Revolutionary War?

    Answer: National Treasure

  60. Pretty much free advertising for Nike, "Air Force Ones" was a 2002 hit single by what St. Louis rapper?

    Answer: Nelly

  61. You might remember her as Lizzie McGuire, but which Disney star transitioned to pop princess with her 2003 album “Metamorphosis,” which featured bonafide bops like “So Yesterday” and “Come Clean?”

    Answer: Hilary Duff

  62. 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

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

    Answer: Aqua Teen Hunger Force

  64. 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

  65. Before taking the role of Dr Shepherd, Patrick Dempsey auditioned for the role of what titular doctor from a different 2000s TV show?

    Answer: Dr Gregory House

  66. 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

  67. What repetitively-named 2000s rock band is led by the singer, songwriter, and guitarist Karen O?

    Answer: Yeah Yeah Yeahs

  68. "More bars in more places" was a mid-2000s commercial slogan for what American technology company?

    Answer: ATT

  69. 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

  70. 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

  71. Alan Moore and Dave Gibbons are the famous writer-artist pair behind what graphic novel that is frequently considered the magnum opus of its medium? In fact, it was the only graphic novel to appear on Time's 2005 list of the "All-Time 100 Greatest Novels" list.

    Answer: Watchmen

  72. Comedian Jensen Karp went viral after allegedly finding sugar-covered remains of shrimp in his box of Cinnamon Toast Crunch. Shortly afterwards, social media platforms realized his wife was one of the stars of what hit 90s ABC/Disney teen series?

    Answer: Boy Meets World

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

    Answer: Christina Aguilera

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

    Answer: Amelie

  75. 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

  76. 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

  77. 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

  78. What was the shoe feature developed by Nike and incorporated in several of their flagship shoes that included a support system of arranged small hollow columns made primarily with polyurethane? The first shoe with this feature was released in 2000.

    Answer: Shox

  79. 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

  80. Bravo turned away from performing arts, drama, and indie films in the early 2000s to focus on pop culture and reality shows. This makeover "started" in 2003 with the launch of what reality series?

    Answer: Queer Eye for the Straight Guy

  81. What “haunting” 2001 film about the struggles of being a teenage girl stars a young Scarlett Johansson and is based on a popular graphic novel by Daniel Clowes?

    Answer: Ghost World

  82. One of the featured big cat trainers in "Tiger King" had been on stage with Britney Spears during a performance at the 2001 MTV Video Music Awards as her song featured a caged tiger that had been wrangled by this person. Who is he?

    Answer: Doc Antle

  83. Airing for 6 seasons from 2005 to 2010, what VH1 reality show featured stars like Biz Markie and Kelly Le Brock doing physical challenges and competing in teams to lose weight?

    Answer: Celebrity Fit Club

  84. 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 Pussycats

  85. 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

  86. Bill Gates appears on the cover of a May 2005 Time Magazine issue. 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.

Or, if you're looking for a more general trivia quiz, we've got you covered there too.

Every week, you'll receive a new trivia quiz, with questions about a range of topics.

Get started with a free four-week trial today!

Is there an error in one of our questions?

We do everything we can to ensure that Water Cooler Trivia's questions are appropriate, relevant, and accurate. Our database has tens of thousands of questions, so we don't always get it right. If you see a question that needs editing, we would love if you let us know here or email [email protected].

Celebrating brains
1,200 companies play Water Cooler Trivia every week
Learn MoreWeekly Trivia For Your Office →