Y2K Superstars
This "princess of pop" debuted in 1999, immediately reaching No. 1 on Billboard with lyrics that will have you listening one more time.
Who is Britney Spears?
She had the highest grossing tour in history, raking in over $2 billion dollars across its nearly 2 year span.
Taylor Swift, with The Eras Tour
Who is Taylor Swift?
I'm working late 'cause I'm a singer. Oh, he looks so cute...
...wrapped around my finger
Espresso - Sabrina Carpenter
She won 5 Grammy Awards in just one night, becoming the youngest artist in history to do so across the big 4 categories.
Who is Billie Eilish?
We'll be listening to this dance album all summer, with an album cover that might've been made on MS Paint.
What is Charli XCX's Brat?
This popstar is The Best of Both Worlds, being a normal girl by day, but wearing a blonde wig and performing to sold out shows by night
Who is Hannah Montana?
This Barbadian superstar launched a luxury fashion house and beauty product manufactuer, which helped to redefine beauty and style in the late 2010s.
Who is Rihanna?
Pictures of last night ended up online, I'm screwed, oh well...
...It's a blacked-out blur, but I'm pretty sure it ruled
Last Friday Night (T.G.I.F.) - Katy Perry
She holds the record for the most Grammy Awards won by a female artist, with 35 total wins.
Who is Beyoncé?
Originally released in 2019 for her album "Lover," this synth-pop track became the Song of the Summer four years later in 2023.
What is Taylor Swift's Cruel Summer?
According to this R&B trio, a scrub is a guy that can't get no love from them, who hang's out the passenger side of his best friend's ride.
Who is TLC?
This "Born to Die" alternative pop star became the first female artist in history to have three albums spend over 300 weeks each on the Billboard 200 chart.
Who is Lana Del Rey?
Everywhere I'm looking now
I'm surrounded by your embrace...
...Baby, I can see your halo
You know you're my saving grace
Halo - Beyoncé
She became the first artist in music history to win Grammy Album of the Year four times.
Who is Taylor Swift?
In this 2021 heartbreak ballad to an ex, she's finally got her driver's license, just like they always talked about.
What is Olivia Rodrigo's driver's license?
Gwen Stefani went No. 1 with "Hollaback Girl," but she originally became famous with this group in the 90s.
What is No Doubt?
In 2026, this 25 year-old artist because the first woman and youngest artist ever to win the BRIT Award for Producer of the Year (after debuting on TikTok just 6 years earlier).
Who is PinkPantheress?
Head in the clouds, got no weight on my shoulders
I should be wiser and realize that I've got...
...One less problem without ya
I got one less problem without ya
Problem - Ariana Grande feat. Iggy Azalea
Before the category was retired, this artist won Best Female Pop Vocal Performance in 2009 for "Chasing Pavements."
Who is Adele?
She seemingly popped out of nowhere in 2024, with drag queen-inspired makeup and a groove that you'd want to order "HOT TO GO!"
Who is Chappell Roan?
She put her thing down, flipped it, and reversed it, in her 2000s hit "Work it," with a reversed sample in the chorus.
Who is Missy Elliot?
At age 16, this New Zealand artist became the youngest solo artist in decades to top the Billboard Hot 100.
Who is Lorde?
I don't know where my soul is
I don't know where my home is...
...and baby, all I need for you to know is
I'm like a bird, I'll only fly away.
I'm Like a Bird - Nelly Furtado
She won in 2026 for her album Mayhem, becoming the first artist in music history to win across all five Pop Field categories over her career.
This British-Albanian pop star dominated the charts with her 2020 disco-infused album Future Nostalgia, but also shared her love for reading through a zoom book club, where she held meetings with famous authors in-between studio sessions.
Who is Dua Lipa?