6 iHeartRadio Editors Recreate Britney Spears' Iconic Music Video Makeup

By Nicole Mastrogiannis

September 14, 2016

Britney Spears Makeup

Britney Spears has released so many iconic music videos over the course of her career. From "...Baby One More Time" to "Oops, I Did It Again," she has created so many amazing looks throughout all of these visuals (we're looking at you school girl outfit and red latex jumpsuit!). With less than a month to go until our 2016 iHeartRadio Music Festival, our feels are out of control with excitement because we can't wait to see her. So, we here at iHeartRadio got our makeup done just like some of Britney's best music video looks in anticipation of next month's festival.

Several of the ladies here at iHeartRadio, myself included, were asked to choose their favorite music video look for two very talented makeup artists to recreate. And the results were AMAZING. Makeup artists Jonny Polizzi and Ruthie Weems, who just did makeup for Beyoncé and Britney's backup dancers -- and DJ Khaled -- at this year's MTV VMAs, came to iHeartRadio HQ in New York City to Spears-ify us all. Check it out:

Maggie, Snapchat Discover Editor - "Oops!...I Did It Again"

Britney Spears "Oops I Did It Again" Makeup

Why she chose this look: "When I think back on iconic Britney looks, the two the come to mind are "...Baby One More Time" and "Oops!...I Did It Again." And this one, to me, was just a little bit more fun. The makeup for this, in particular, is super, super iconic, and the late '90s/early 2000s are coming back, so I wanted to bring out my inner 'Oops.'"

How she felt after the makeup was complete: "I loved it! It was unbelievable, and I wanna say that I felt just a little bit more Britney. I just kind of slayed the rest of my day."

Favorite Britney song(s): "I think I'd have to go with '...Baby One More Time' because it, to me, is one of the most perfect pop songs of all time, Britney Spears or otherwise. But I do have to say that 'Toxic' is one of my favorite songs to run to, and that will forever be top tier."

Rachel, Photo Editor - "Stronger"

Britney Spears

Why she chose this look: "I didn't know what look to choose, and James [iHeartRadio Music Editor] is the biggest Britney Spears fan. So I said, 'James, which look should I choose?' and he immediately said 'Stronger.'"

How she felt after makeup was complete: "Like a QUEEN. I was obsessed with the look, and I never wanted to take it off."

Favorite Britney Song(s): "It varies, but 'Radar,' maybe right now."

Nicole - Entertainment Editor, "Toxic"

Britney Spears "Toxic" Makeup

Why she chose this look: "This has to be one of my favorite Britney looks from her music videos ever. And anyone who knows me, knows that I love ANYTHING that's sparkly ... like her crystal/nude bodysuit in the 'Toxic' video. And I not only like the look because of the sparkles, but it's somewhat of a natural makeup look as well. I would definitely wear this makeup look out during a night out with my friends. Also, sparkles."

How she felt after makeup was complete: "I felt like a GODDESS. I loved the sparkles in the corners of my eyes and those long lashes -- two of my favorite things when it comes to makeup. And, I did not want to take my makeup off. In fact, this is so bad because you should always take your makeup off before you go to bed, but I fell asleep in my makeup. ANd when I woke up to go to the gym in the morning, I still didn't want to take it off! But I did 😞"

Favorite Britney Song(s): "I've been a fan of Britney Spears since '...Baby One More Time' came out -- it was the inspiration for my 6th Grade Halloween costume. So to pick a favorite song of hers is extremely hard ... like taking the SATs hard. BUT, two of my favorites of all time definitely include "Oops!...I Did It Again" and "Crazy" because I can vividly remember watching the music videos over and over and learning all of the choreography, and then performing it for my family and friends."

Tracy, Director of Social Media & Content - "I'm A Slave 4 U"

Britney Spears "Slave 4 U" Makeup

Why she chose this look: "As I was thinking about all the different Britney videos, 'Slave' is the one that I just remember her having the most epic look, because she's glistening, she's sweaty, she has this really amazing sexy, sultry teal blue eye. That was just the peak of Britney Spears's sexuality and her being super attractive, her body was in ridiculous shape. I think that was just the height of my Britney fandom. I still love her, but that was the height of it."

How she felt after makeup was complete: "I didn't look in the mirror the entire time that she was doing it, and just seeing everyone react as it was being put on me was awesome because I didn't know what was happening. I'm very pale in real life, and everyone just said 'you're SO tan!' She did this amazing bronzing; she made me look so tan. And then when I looked in the mirror, I could not believe how amazing the eye makeup was. It didn't take that long, and it made my eyes pop, and seem huge. It was awesome. I didn't ever wanna take it off."

Favorite Britney Song(s): "I love 'Till The World Ends,' I love 'Toxic,' I love '...Baby One More Time,' I do that at karaoke. I think it's 'Toxic' though.

Isha, Associate Editor - "Hold It Against Me"

Britney Spears "Hold It Against Me" makeup

Why she chose this look: "I chose her cat eye in 'Hold It Against Me' because I just really love cat eyes. And then, the bottom of her face looked really natural, so I figured natural mixed in with some extra-ness around my eyes would be really cute."

How she felt after makeup was complete: "I loved it. My face never looked like that before. And the lashes that he added on were really big and dramatic. So, I liked it. I had fun!"

Favorite Britney Song(s): "My favorite Britney song in the past would probably be 'Oops!...I Did It Again.' But more recently, I like 'Gimme More.'"

Katherine, Photo Editor - "I'm A Slave 4 U" VMA Performance

Britney Spears "I'm A Slave 4 U" VMA Makeup

Why she chose this look: "To be honest, I didn't realize how theatrical it was. I was like 'Oh yea, the memorable performance of when Britney had the snake. I'm gonna do that.' And I just went for the moment, rather than looking at the makeup. And then, after the fact, I was like 'Oh my God, she had a lot of makeup on, and I look really night in the middle of the day."

How she felt after makeup was complete: "It was amazing, I felt like I could ... Wendy and Kendra [iHeartRadio photo editors] said that I should be on stage presenting somewhere at an awards show. So, I had a lot of makeup on. It was really heavy and camera-ready."

Favorite Britney Song(s): "If I was doing a real #TBT, it would be something like 'Lucky.' But, really, I love 'Toxic.' When that came out in high school, I loved that one because it was the party/turn-up song."

 Needless to say we are all VERY excited to see Brit do her thing on the iHeartRadio Music Festival stage in Las Vegas in only 10 MORE DAYS! Check out how our Britney makeup transformations came to life and GLORY (see what I did there 😉) in the video below:

Photos: Rachel Kaplan for iHeartRadio, Getty Images, Vevo

Britney Spears
Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.