Music
Which boy band released the smash hit "Bye Bye Bye" in the year 2000?
NSYNC
Which 2001 comedy starring Reese Witherspoon features the tagline "Trying to fit in. Born to stand out"?
Legally Blonde
What iconic pop star famously shaved her head and hit a paparazzo's car with an umbrella during a media frenzy in 2007?
Britney Spears
Which social media platform, launched in 2003, featured a customizable profile layout and a default friend named Tom?
MySpace
Which futuristic electric car company, founded in 2003, released its first production vehicle called the Roadster in 2008?
Tesla
Who won the very first season of American Idol in 2002?
Kelly Clarkson
What is the name of the fictional paper company featured in the American version of The Office, which premiered on NBC in 2005?
Dunder Mifflin
Which reality TV star couples' lavish, televised 2011 wedding lasted only 72 days before they filed for divorce?
Kim Kardashian and Kris Humphries
What sleek, slide-out keyboard cell phone brand became the ultimate status symbol for celebrities and teens in the mid-2000s?
T-Mobile Sidekick
Which Japanese sports car, famously driven by Paul Walker's character Brian O'Conner, became an instant tuner icon in the early 2000s?
Nissan Skyline GT-R (specifically the R34)
What was the title track of Britney Spears' sophomore album released in 2000?
Oops!... I Did It Again
Which 2009 James Cameron film became the highest-grossing movie of all time by taking viewers to the planet Pandora?
Avatar
Which singer experienced a controversial "wardrobe malfunction" during the 2004 Super Bowl halftime show alongside Justin Timberlake?
Janet Jackson
What video-sharing website was founded in February 2005 by three former PayPal employees and later bought by Google?
YouTube
What massive, military-derived SUV brand became the ultimate status symbol for celebrities and rappers in the early 2000s before being discontinued in 2010?
Hummer (specifically the H2)
Which specific song holds the record for the longest climb to number one on the Billboard Hot 100 during the Y2K era, taking 32 weeks to reach the top in 2000?
"With Arms Wide Open" by Creed
What 2006 satirical comedy film stars Sacha Baron Cohen as a fictional Kazakh journalist traveling across the United States?
Borat
Which TV host suffered a highly publicized mishap in 2005 when she accidentally leaked her own cell phone contact list, exposing numbers for Eminem and Victoria Beckham?
Paris Hilton
What was the name of the peer-to-peer internet telephony network that eBay acquired for $2.6 billion in 2005, only to sell it off a few years later?
Skype
What iconic retro-styled sports car did Ford completely redesign in 2005, triggering a massive wave of nostalgic muscle car revivals from Chevy and Dodge?
Ford Mustang (Fifth Generation)
Before finding massive fame with his own solo work, which future R&B superstar co-wrote the 2001 hit song "Survivor" for Destiny's Child?
Anthony Hamilton (or co-producer Anthony Dent)
What specific cable network originally passed on the hit series Mad Men in the early 2000s before AMC eventually picked it up years later?
HBO (and later Showtime).
What specific item did actor Winona Ryder get caught shoplifting from a Beverly Hills Saks Fifth Avenue store in late 2001?
Thousands of dollars worth of designer clothes and accessories (including a Marc Jacobs sweater).
What specific name did Google give to its first-ever branded Android smartphone, manufactured by HTC and released in January 2010?
Nexus One
What ultra-luxury British brand was officially acquired by German automaker BMW in 2003, kicking off a new era with the launch of the massive Phantom sedan?
Rolls-Royce