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100

This artist has hit songs such as "I Can't Wait", "Why Not", and "Come Clean".

Who is Hilary Duff?

100

The Marvel Cinematic Universe began with this movie in 2008.

What is Iron Man?

100

The host of MTV's Total Request Live (TRL).

Who is Carson Daly?

100

This article of clothing was worn with a dress. 

What are jeans?

100

These two buildings were destroyed during a terrorist attack on September 11, 2001.

What are the Twin Towers?

or

What is the World Trade Center?

200

This singer had a lip synch malfunction during a performance on Saturday Night Live.

Who is Ashlee Simpson?

200

This Disney animated movie made history by introducing the first black Disney princess.

What is The Princess and The Frog?

200

This show premiered on Disney Channel in 2003 and ran until 2007 where it made history by being the first Disney Channel show to run more than 60 episodes. 

What is That's So Raven?

200

The shutter shade trend only grew 'Stronger' in the late 2000s after this rapper began wearing them.

Who is Kanye West?

200

This superstar singer and entertainer passed away due to doctor negligence on June 25th, 2009. 

Who is Michael Jackson?

300

This producer was the 'King of Crunk' in the mid to late 2000s with albums such as "Put Yo Hood Up" and "Crunk Juice".

Who is Lil Jon?

300

This 2006 horror film only gave you 7 days to live.  

What is The Grudge?

300

This popular mockumentary styled television show premiered in 2005.

What is The Office?

300

Adjust your Top 8, because all your friends went crazy over this early form of social media.

What is Myspace?

300

This Senator from Illinois made history in 2008 by beating his republican opponent for the highest office in the United States.

Who is Barack Obama?

400

This country singer has a hit album titled "Room to Breathe" that was released on November 18th, 2003.

Who is Reba McEntire?

400

After his death in 2008, Heath Ledger posthumously won an Academy Award for best supporting actor in this movie.

What is The Dark Knight?

400

Paula Abdul, Simon Cowell, and Randy Jackson were judges for what reality television program?

What is American Idol?

400

These popular spinning top toys share the same name as its Japanese anime counterpart. 

What are Beyblades?

400

What catastrophic event flooded New Orleans in 2005?

What is Hurricane Katrina?

500

This band won Best Hard Rock Performance at the Grammy awards in the early 2000's for songs like "Alive" and "Youth of the Nation".

Who is P.O.D.?

500
Sir Ian McKellen and Elijah Wood both starred in this popular movie series adapted from a book series of the same name.

What is Lord of the Rings?

500

This actress proved she was more than 'All That' with her spin-off sketch comedy show that aired on Nickelodeon until 2002.

Who is Amanda Bynes?

500

The 'sharp' Motorola flip phone everyone wanted in 2004 because of its sleek thin design.

What is the Motorola RAZR?

500

This dystopian teen book series came out in 2008.

What is The Hunger Games series?

Or 

What is The Hunger Games?