This controversial cover featured a 17-year-old Britney turned sex symbol in lingerie and co-starred a Teletubby.
4. Justin Timberlake years (1999-2002)
This short-lived relationship remains the best of teen pop royalty and created an unforgettable red carpet look that can only be described as denim.
5. "Oops!... I Did It Again" video (2000)
This video proved Britney was much more than a one-hit wonder and made us all want a red jumpsuit.
6. The Snake Performance (2001)
The name of the albino Burmese Python from Britney's "Slave 4 U" VMA performance was Banana.
7. "Toxic" video (2003)
This release set a new standard for music videos and features Britney wearing nothing but diamonds.
8. Madonna kiss (2003)
When Britney, Christina Aguilera and Madonna began their surprise performance at the VMAs, it didn't seem like the moment could get any better... until the pop queen planted a kiss on the pop princess.
9. "Womanizer" comeback (2008)
After having a public meltdown, Britney dropped comeback single "Womanizer" and released her "Circus" album, proving she wasn't just stuck in the '90s.
Click through the gallery below to see photos of Britney Spears & her boyfriends through the years:
Britney Spears & boyfriends through the years
Britney Spears & boyfriends through the years
New pop artist Britney Spears smiles for the cameras during the 26th annual American Music Awards held at the Shrine Auditorium in Los Angeles, Monday, Jan. 11, 1999. (AP Photo/Mark J. Terrill)
The 18-year-old U.S. pop star Britney Spears smiles for photographers during a news conference in Cologne, Germany, Monday, April 17, 2000, where she presented her new album "oops!... I did it again." (AP Photo/Hermann J. Knippertz)
Show host Britney Spears, left, and Justin Timberlake of N'Sync arrive at the 28th Annual American Music Awards in Los Angeles Monday, Jan. 8, 2001. (AP Photo/Mark J. Terrill)
Pop star Britney Spears, right, star of the new film "Crossroads," shares a laugh with her boyfriend Justin Timberlake of the pop group 'N Sync at the premiere of the film at the Grauman's Chinese Theater in the Hollywood section of Los Angeles, Monday, Feb. 11, 2002. (AP Photo/Chris Pizzello)
Entertainers Justin Timberlake and Britney Spears wave to the crowd prior to the start of the 2002 NBA All-Star game in Philadelphia, Sunday, Feb. 10, 2002. (AP Photo/Chris Gardner)
UNITED STATES - SEPTEMBER 28: Britney Spears sits at a screening of 'Drive Me Crazy' at Union Square Theater with Robbie Carrico. (Photo by Richard Corkery/NY Daily News Archive via Getty Images)
Jason Alexander, Britney Spears' childhood friend who was married to her before the marriage was annulled in 2004, poses during the opening of the Beverly Hills Pimps and Hos clothing store, to benefit Peace Over Violence, Friday, Dec. 8, 2006, in Los Angeles. (AP Photo/Danny Moloshok)
LAS VEGAS - DECEMBER 08: Musician Britney Spears and husband Kevin Federline arrive at the 2004 Billboard Music Awards at the MGM Grand Garden Arena on December 8, 2004 in Las Vegas, Nevada. (Photo by Frazer Harrison/Getty Images)
Britney Spears, right, looks up at her husband Kevin Federline as they are interviewed while arriving for the LG Mariah Carey and Jermaine Dupri Post Grammy Party at a private residence Wednesday, Feb. 8, 2006, in Beverly Hills, Calif. (AP Photo/Danny Moloshok)
Britney Spears arrives with her boyfriend Adnan Ghalib (R) at the Los Angeles County Superior courthouse 14 January 2008 for a hearing regarding visitation rights for her two sons that she has with ex-husband Kevin Federline. AFP PHOTO/Gabriel BOUYS (Photo credit should read GABRIEL BOUYS/AFP/Getty Images)
Britney Spears, right, and Jason Trawick arrive at an Evening of "Southern Style" presented by The St. Bernard Project and the Spears Family in Beverly Hills, Calif., Wednesday, May 11, 2011. The St. Bernard Project is a non-profit organization that provides relief work for survivors of Hurricane Katrina. (AP Photo/Matt Sayles)
Jason Trawick (L) and Britney Spears arrive at the 2011 MTV Video Music Awards (VMAs) August 28, 2011 at the Nokia Theatre in downtown Los Angeles, California. AFP PHOTO / Frederic J. Brown (Photo credit should read FREDERIC J. BROWN/AFP/Getty Images)
LOS ANGELES, CA - SEPTEMBER 11: Singer Britney Spears (L) and fiance agent Jason Trawick appear at the premiere of Fox's 'The X Factor' Season 2 and handprint ceremony at the Chinese Theatre on September 11, 2012 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)
WEST HOLLYWOOD, CA - MARCH 02: Recording artist Britney Spears (L) and David Lucado attend Neuro at the 22nd Annual Elton John AIDS Foundation Academy Awards Viewing Party at The City of West Hollywood Park on March 2, 2014 in West Hollywood, California. (Photo by Charley Gallay/Getty Images for Neuro)
Britney Spears, left, and Charlie Ebersol arrive at the Billboard Music Awards at the MGM Grand Garden Arena on Sunday, May 17, 2015, in Las Vegas. (Photo by Eric Jamison/Invision/AP)