Music
This massive Latin pop crossover star had everyone doing the "Cup of Life" and "Livin' la Vida Loca" in 1999.
Ricky Martin
This 2004 cult-classic indie comedy features a tater-tot-loving teenager from Idaho, an election for student body president, and a legendary dance routine to Jamiroquai's "Canned Heat."
Napoleon Dynamite
This MTV prank and stunt show, starring Johnny Knoxville and Bam Margera, premiered in 2000 and always started with a strict "Do not attempt this at home" warning.
Jackass
In 2004, this legendary 19-year-old rookie LeBron James won the NBA Rookie of the Year award while playing for which hometown franchise?
Cleveland Cavaliers
Boasting customizable away messages and an iconic yellow running man mascot, this desktop instant messaging program ruled teen communication in the Y2K era.
AIM (AOL Instant Messenger)
In 2002, Vanessa Carlton released this ubiquitous piano-pop anthem whose music video featured her driving a moving platform piano down a highway.
A Thousand Miles
This 1999 experimental indie horror film terrified audiences using mockumentary-style handheld camera footage of three student filmmakers lost in the Maryland woods.
The Blair Witch Project
This long-running Nickelodeon animated series, premiering in 2001, featured a 10-year-old boy named Timmy Turner who had to navigate the chaos of having two magical, floating fairy godparents named Cosmo and Wanda.
The Fairly Oddparents
At the 2002 World Cup, this legendary Brazilian striker rocked one of the worst haircuts in sports history (a shaved head except for a semi-circle fringe) but still led his country to victory.
Ronaldo
Long before the phrase "social media" existed, thousands of teenagers learned basic HTML just to code their profiles on this early networking site, which featured a default first friend named Tom.
Myspace
In 2003, this pop princess famously made global headlines by sharing a shocking onstage kiss with both Britney Spears and Christina Aguilera during the MTV Video Music Awards performance.
Madonna
"First rule of Fight Club: You do not talk about Fight Club." What was the name of Brad Pitt’s charismatic, soap-making alter ego in this 1999 cult classic?
Tyler Durden
On the hit cartoon Family Guy, which officially returned to FOX in 2005 after being canceled, Peter Griffin spends multiple episodes engaged in incredibly violent, absurdly long, city-destroying fistfights with an unnamed, giant animal. What kind of animal is it?
A Giant Chicken
At the 2002 Winter Olympics in Salt Lake City, this American speedskater became a massive Y2K breakout star, winning gold and gold/silver medals while rocking his signature soul patch and frosted hair.
Apolo Anton Ohno
Released in late 2000, this indestructible mobile phone featured a customizable plastic shell, a remarkably long battery life, and the highly addictive game Snake II. What was the brand?
Nokia
This file-sharing platform, co-founded by Shawn Fanning in 1999, completely revolutionized how the Y2K generation got their MP3s before being shut down for copyright infringement.
Napster
This 1999 romantic comedy, starring Julia Roberts and Hugh Grant, features the famous line: "I'm also just a girl, standing in front of a boy, asking him to love her."
Notting Hill
On the animated sci-fi hit Futurama, which premiered in 1999, what was Philip J. Fry's actual profession in the 20th century before he was accidentally cryogenically frozen?
Pizza Delivery Boy
In one of the most famous college football endings ever, this team won the 2003 Fiesta Bowl National Championship in double overtime against the Miami Hurricanes after a highly controversial, late pass-interference flag.
Ohio State Buckeyes
Long before the iPad, tech-savvy professionals in the early 2000s kept track of their calendars and emails using a "PDA" (Personal Digital Assistant). Which dominant company manufactured the most famous line of these pocket-sized stylus devices, including models like the m100 and the V?
Palm (or PalmPilot)
This masked hip-hop legend, famous for his iconic metal face-guard, released his underground masterpiece album Madvillainy alongside producer Madlib in 2004.
MF DOOM
This 2004 romantic sci-fi drama features Jim Carrey and Kate Winslet as a couple undergoing a high-tech medical procedure to physically erase each other from their memories.
Eternal Sunshine of the Spotless Mind
Before finding massive success as a movie star, Jennifer Garner played CIA double-agent Sydney Bristow on this high-octane ABC spy thriller that premiered in 2001.
Alias
This American figure skater won a shocking, historic gold medal at the 2002 Salt Lake City Winter Olympics at just 16 years old after an flawless long program jumped her up from 4th place.
Sarah Hughes
Launched in 1998, this candy-colored, translucent desktop computer saved Apple from financial ruin and became the ultimate early-2000s school computer lab staple.
iMac G3