The Best Britney Spears Moments of All Time (VIDEOS)
You better work b**ch.

Britney Spears's career has been a wild ride. The pop princess started off sweet, then sexy, then troubled, and then made an epic comeback. Oh, and there was the K. Fed phase, as well. In celebration of her Vegas residency, her new album, and her two-hour E! documentary, we're giving you all the Britney goods from the past two decades. Don't call it a comeback, she's been here for years.
...Baby One More Time, 1999
VMAs, 1999
(You Drive Me) Crazy, 1999
VMAs, 2000
Oops! I Did It Again, 2000
I'm Not A Girl, Not Yet A Woman, 2001
Stay In The Know
Get exclusive access to fashion and beauty trends, hot-off-the-press celebrity news, and more.
Toxic, 2003
VMAs, 2003
Billboard Music Awards, 2011
Related Stories:
The Best and Worst Hairstyles of 2013
Our Favorite Celebrity Instagram Shots
Topics We Hope Tina & Amy Spoof at the 2014 Golden Globes
Follow Hallie Gould on Twitter.
Hallie has worked in beauty editorial for ten years and has been editorial director at Byrdie since 2021. Previously, she was a senior editor at Byrdie since 2016. During her time at Byrdie, she's written hundreds of high-performing stories on skincare, wellness (including fitness, diet, mental health, body image, et al) makeup, and hair. She's a regular on set, helping to source inspiration for makeup and hair looks, as well as interviewing celebrities, models, and other notable women and men in the beauty space.
Before that, Hallie ran Marie Claire's social media and wrote beauty and culture stories for the site, and helped launch Time Inc.'s digital-only beauty brand, MIMI. After college, she contributed to Time Out New York’s Shopping & Style section before landing her first beauty editor gig at Hearst's Real Beauty. Hallie's writing has also appeared in ELLE, Cosmopolitan, and InStyle. Hallie graduated with a BA in Communication Arts from the University of Wisconsin-Madison.
-
Louis and George Are Having a Ball at Trooping the Colour
Their matching outfits are simply the icing on the cake.
-
Kate and Charlotte Showcase Their Mother-Daughter Style
The little princess twinned with her mom in the best way.
-
Kate Middleton Channels Princess Diana at Trooping the Colour 2025
The Princess of Wales even wore the same designer as her late mother-in-law.
-
Britney Spears Celebrates "Best Christmas of My Life" With Her Son
After two years of estrangement, the pop singer reunited with her younger son.
-
Britney Spears Calls Out Selena Gomez and Pamela Anderson as Some of Her "Girl Crushes"
Women admiring women!
-
Sabrina Carpenter Says She Receives the Same "Vilification" That Britney Spears Did for Embracing Her Sexuality
Ugh.
-
Jennifer Lopez and Ben Affleck's Divorce Lawyer Has Also Worked With Kim Kardashian, Britney Spears, and Angelina Jolie
Meet Laura Wasser.
-
Megan Thee Stallion Pays Homage to Britney Spears at the 2024 VMAs With a Snake—That She Demanded Be Taken Off Her
The rap superstar hosted this year's award show and called back one of the pop icon's most memorable performances.
-
Macy Gray Says Britney Spears Once Skateboarded Into Her Recording Session
??????
-
Britney Spears' Song "Criminal" Is Climbing the Charts After Justin Timberlake's DWI Arrest
Oh, no...
-
Britney Spears Says "All My Jewelry Was Stolen" In Instagram Post
"It's hard to buy new now because I'm scared it will go missing."