Category 1: TRL & Radio Hits
Category 2: TV After School
Category 3: Movies We Wore Out on VHS/DVD
Category 4: Fashion Crimes (But We Loved Them)
Category 5: Tech Before Smartphones
100

This boy band asked us to tell them why.

Who is Backstreet Boys?

100

Did I do that?” came from this sitcom character.

What is Family Matters?

100

As if!” came from this teen movie.

 What is Clueless?

100

These pants were low-rise and emotionally dangerous.

What are Low-rise jeans?

100

This device let you rewind songs manually.

What is A cassette tape?

200

This teen pop star sang Genie in a Bottle.

Who is Christina Aguilera?

200

– This show made vampires hot before it was cool.

What is Buffy the Vampire Slayer?

200

This movie had us afraid to let go… literally.

What is Titanic

200

This brand was famous for velour tracksuits.

What is Juicy Couture?

200

This service screamed “You’ve got mail!”

 What is AOL?

300

This rapper taught us it was “Hard Knock Life.”

Who is Jay-Z?

300

This teen drama took place in Beverly Hills, ZIP code included.

What is Beverly Hills, 90210?

300

This horror franchise taught us not to answer the phone.

What is Scream?

300

These shoes were platform and very unstable.

What are Platform sandals?

300

This phone famously flipped open.

 What is A flip phone?

400

This R&B group gave us No Scrubs

Who is TLC?

400

 This show followed six friends living unrealistically large in NYC.

What is Friends?

400

This movie launched a whole cheer culture obsession.

What is Bring It On?

400

 This accessory often matched your flip phone.

What is A bedazzled phone case?

400

This music player held “1,000 songs in your pocket.”

What is iPod?

500

 This singer dominated the charts with Crazy and Survivor.

Who is Destiny’s Child?

500

This animated show featured a yellow family in Springfield.

 What is The Simpsons?

500

This movie introduced us to bullet time and leather trench coats.

What is The Matrix?

500

 This hairstyle involved frosted tips or butterfly clips

What is Early 2000s hair trends?


500

This internet sound meant someone picked up the phone.

What is The dial-up disconnect sound?