When Jann Arden sang the best 🚩 red flag 🚩 anthem of the 90s

When Republica was READY TO GO in the 90s

When Salt-n-Pepa and En Vogue had the BEST duet of the early 90s

When Andrew W.K. had the loudest Y2K party anthem

When Jessica Simpson sang a song with YOUR name in it

When The Calling had the most Y2K movie pop rock love song

When Snow Patrol had the perfect love song about wasting time

When Colbie Caillat had the cutest love song of the 2000s

When Christina Aguilera had 2 versions of the same song at the same time

Edwin McCain: "I'll Be" wasn't a love song (but then it was)

When Kylie Minogue had the best futuristic pop love song of Y2K

When Corinne Bailey Rae had the best chill out anthem of the 2000s

When Jump5 had the most Disney pop song

When Paris Hilton was almost a pop star in the 2000s

When the A*Teens sang the sugariest Y2K pop song

When Christina Aguilera had her big band and swing era (ft. @JarredJermaine)

When Lindsay Lohan wrote on of the most honest pop songs

When Alanis Morissette had the wisest pop rock song of the 90s

When All-American Rejects made a classic 90s anthem their own

When Jessica Simpson turned a hit 80s song into a new 90s hit song

When B*Witched sang the happiest 90s pop song ever

When Hilary Duff sang the soundtrack to our high school break ups

When Mandy Moore had the most bubblegum pop song of the 90s

When Jessica Simpson sang the most dramatic teen pop song of the 90s

When Ashlee Simpson sang the perfect Y2K pop rock anthem

The All-American Rejects: "Gives You Hell" and "Flagpole Sitta"

When Duffy was almost the next Amy Winehouse

All-American Rejects react to a pop punk version of their song!

When Lindsay Lohan sang a Y2K pop banger

All-American Rejects react to a soulful version of their song!