“Teenage Dirtbag” (’00)

Remember when everyone was obsessed with the adorability of Taylor Swift’s “You Belong with Me”? Well, the men of Wheatus had figured out the musical gold of telling the story about a loner getting with the person of his or her dreams in “Teenage Dirtbag” long before Taylor Swift started racking up breakups. The pitch (aside from the seemingly random falsetto toward the latter half of the song) is easily replicated, making it an excellent song for all vocal ranges to belt on the drive to school. If you still need a reason to dig up your Walkman and push play, some of the lyrics capture high school in the grunge era so perfectly that listening to it could almost be considered research for an APUSH decades project.

“Say My Name” (’99)

Before Beyoncé was crowned Queen, she and her co-princesses of Destiny’s Child brought “Say My Name” to the ears of suspicious girlfriends everywhere. With quite possibly the catchiest background beat musically possible, the ladies of Destiny’s Child relayed the tale of catching a significant other cheating—while on the phone. This story alone is enough to captivate listeners, but when paired with the killer chorus with the leading vocals by Beyoncé, it’s no wonder “Say My Name” topped the Billboard 100 for three weeks straight in 2000. While “Bootylicious” may be requested more frequently at your Junior Prom, “Say My Name” is the Destiny’s Child song to rule the millennium era.

“Lucky” (’00)

It proves difficult to select only one of Britney Spears’ singles between 1999 and 2000 to praise, but “Lucky” was certainly one of the best. Although it is an unrivaled power ballad, it is not necessarily the melody or catchiness of “Lucky” that makes it an extraordinary song––it’s the message that it represents. “Lucky” is about a girl who from the outside has it all, but on the inside feels unfulfilled. Spears conveys a positive lesson that not all is what it seems and one should pursue what satisfies him or herself rather than what pleases society. Although not as popular as “Oops!…I Did It Again” and “Baby One More Time,” “Lucky” is a classic pop anthem with a message that still rings true today.

“No Scrubs” (’99)

Before TLC gifted the world with their R&B hit “No Scrubs,” no apt way for women to tell creepy losers to leave them alone existed. “No Scrubs” was TLC’s third number one single, and it basically told all immature, overly confident people to evaluate the way the way they present themselves before approaching their love interests. It also doubles as a sassy track to belt after a bad break-up or disappointing date.This song was nominated for “Record of the Year” at the 2000 Grammy’s, but it’s real claim to fame is the effect it had on the dating population.

“It’s Gonna Be Me” (’00)

Perhaps the most belt-worthy song in musical history, “It’s Gonna Be Me” by NSYNC is about a desperate man looking to win over a reluctant woman. Never has such a plea been made by a player than on this track. At first the desperate message seems pathetic, but when all the boy band’s members collectively assert that when she finally gets to love somebody, “Guess what? It’s gonna be me,” and you know NSYNC means business. This single peaked at number one on the Hot 100 and deservedly so. Arguably, even NSYNC’s other hits pale in comparison to the greatness of “It’s Gonna Be Me.”

“Waiting For Tonight” (’99)

Jennifer Lopez’s “Waiting For Tonight” has a chorus so captivating that one cannot avoid involuntarily screaming along. This pre-“Jenny From the Block” era track peaked on the Hot 100 and can succinctly be described as a turn of the millennium party anthem. Underneath the slightly Spanish infused dance beat, Lopez tells a story about the pain of longing for a loved one. Unlike her repertoire today, which seems to consist of solely shallow club songs and the occasional Pitbull appearance, “Waiting For Tonight” is a reminder of how passionate the Latina songstress can be.