Security personnel keep a watchful eye on zealous fans as Britney Spears arrives for the premiere of “Drive Me Crazy” in New York City on September 28, 1999. Earlier that year, Spears’ “Baby One More Time” topped the Billboard singles and albums charts. Photo by Ezio Petersen/UPI | License Photo
Spears won Female Artist of the Year at the Billboard Music Awards in Las Vegas on December 10, 1999. She was also awarded New Artist of the Year, Female Hot 100 Singles Artist of the Year and Female Album Artist of the Year. Photo by Nasser Khan/UPI | License Photo
Spears performs live on “Today” in New York City on June 30, 2000. Earlier that year, Spears topped the Billboard video sales charts for “Time Out.” Photo by Ezio Petersen/UPI | License Photo
Spears performs her song “Stronger” during her Got Milk Tour in Maryland Heights, Mo., on July 16, 2000. Photo by Bill Greenblatt/UPI | License Photo
Spears was nominated for Best Dance Video, Best Female Video, Viewer’s Choice and Best Pop Video at the MTV Video Music Awards in New York City on September 7, 2000. Thirteen years later, the star recreated her performance from the awards show for her Las Vegas residency. Photo by Laura Cavanaugh/UPI | License Photo
Spears won Albums Artist of the Year and Biggest One-Week Sales of an Album Ever by a Female Artist for her album “Oops!… I Did It Again” at the Billboard Music Awards in Las Vegas on December 5, 2000. Photo by Russ Einhorn/STAR MAX/UPI | License Photo
Spears (L) and then-boyfriend Justin Timberlake, of the vocal group ‘NSync, arrive at the Jive Records New York party to celebrate the release of Spears’ new album, “Britney,” in New York City on November 6, 2001. The couple met on the set of “The All-New Mickey Mouse Club” and started dating in 1999 and split in 2002. Photo by Ezio Petersen/UPI | License Photo
Spears answers reporters’ questions at the opening of her first new restaurant NYLA in New York City on June 27, 2002. The restaurant closed the next year. Photo by Ezio Petersen/UPI | License Photo
Spears performs during the NFL Kickoff celebrations on the National Mall in Washington, D.C., on September 4, 2003. Earlier that year, Spears’ film “Crossroads” was nominated for Golden Raspberry Awards. Photo by Michael Kleinfeld/UPI | License Photo
Spears arrives at the Glamour Women of the Year awards in New York City on November 10, 2003. The following year, Spears’ and dancer Kevin Federline got married and split in 2006. The couple has two sons together, Preston Federline and Jayden Federline. Photo by John Angelillo/UPI | License Photo
Spears poses at the launch for her new album “In the Zone” in New York City on November 18, 2003. The day before, she was honored with the 2,242nd star on the world famous Hollywood Walk of Fame. Photo by Ezio Petersen/UPI | License Photo
Spears won Top-Selling Dance Single of the Year for “Me Against the Music” at the Billboard Music Awards in Las Vegas on December 8, 2004. A couple months prior, Spears said in a letter published on her website she was going to take some time off to get some rest. Photo by Roger Williams/UPI | License Photo
Spears won Video of the Year, Best Pop Video and Best Female Video for “Piece of Me” at the MTV Video Music Awards in Los Angeles on September 7, 2008. Photo by Jim Ruymen/UPI | License Photo
Spears (L) performs with Madonna during her “Sticky and Sweet” tour in Los Angeles on November 6, 2008. Later that month she appeared on an MTV documentary where she said her life was devoid of passion following a court decision to give her father control over her interests. In 2020, her sister would earn control of her trust. Photo by Jim Ruymen/UPI | License Photo
Spears performs during her first ever tour in Russia in Moscow on July 21, 2009. Later that year, her record company released a singles collection celebrating 10 years in the music industry. Photo by Anatoli Zhdanov/UPI | License Photo
Spears arrives at the MTV Video Music Awards in Los Angeles on August 28, 2011. That summer, Nicki Minaj joined Spears on her “Femme Fatale” tour as a special guest. Photo by Jim Ruymen/UPI | License Photo
Spears, who performs “Ooh La La” in “The Smurfs 2”, attends the premiere with her sons Sean Federline (L) and Jayden James Federline in Los Angeles on July 28, 2013. Photo by Jim Ruymen/UPI | License Photo
Spears appears backstage with the fan-voted award she garnered for Favorite Pop Artist at the People’s Choice Awards in Los Angeles on January 8, 2014. That year she began her residency in Las Vegas that she ended in 2018. Photo by Jim Ruymen/UPI | License Photo
Spears performed at the Billboard Music Awards in Las Vegas on May 17, 2015. Photo by Jim Ruymen/UPI | License Photo
Spears presented at the MTV Video Music Awards in Los Angeles on August 30, 2015. Photo by Jim Ruymen/UPI | License Photo
Spears was honored with the Millennium Award and performed her greatest hits at the Billboard Music Awards in Las Vegas on May 22, 2016. Photo by Jim Ruymen/UPI | License Photo
Spears performed at the MTV Video Music Awards, following the release of her ninth studio album, in New York City on August 28, 2016. Photo by John Angelillo/UPI | License Photo
Spears was honored with the Vanguard Award at the GLAAD Media Awards for promoting equality and acceptance in Beverly Hills, Calif., on April 12, 2018. Photo by Jim Ruymen/UPI | License Photo
Spears attends the premiere of “Once Upon A Time In America” in Los Angeles on July 22, 2019. A few months prior, Spears shared a video assuring her fans that she was doing well and taking some time to focus on her mental health. Photo by Jim Ruymen/UPI | License Photo
