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The week of July 12 - July 16 in 1999, Britney Spears was a guest on MTV's TRL Week from Bahamas, where she chatted with Dave Holmes each of the five days from the paradisiacal destination. The show was part of the special that MTV had for the Summer, which included shows that featured several celebrities as guests, as well as a series of concerts at the beach, such as Limp Bizkit.

On November 10, 2003, Queen of Pop Britney Spears performed at New York's Times Square two of her new songs to promote her upcoming album In the Zone: Me Against the Music and (I Got That) Boom Boom featuring the Ying Yang Twins, as part of TRL's Spankin New Music Week. Later that night, she attended the Glamour Magazine's Women of the Year Awards, where she received none other than the Woman of the Year Award. Not only that, but judging by the candids of that day, it seems like she also had an interview with MTV Hits that same day (was she a robot or what ) or she just dressed the same Earlier that day, she was also seen doing some shopping in New York

It took such a long time to get this back up but I’m really excited to present to you by documentary on Aaliyah. It took me about a year to make and I interviewed several fans including some exhalers who grew up listening to her music to assist with telling her story. I also get into why people of the last generation and a half are not familiar with much of her discography despite knowing how she looked, etc. Britney makes a few appearances as I seek to showcase pop culture at the time vs now, and illustrate how music consumption has changed. I also make a commentary on the political landscape when Aaliyah died. I get into the 2012 drake/40 album that never happened, JoJo’s story, why we couldn’t stream Blackground’s albums and more! I’d really appreciate if you could check it out @Jordan Miller @Midnight if you could feature this I would really really be grateful!

On February 17, 2003, the TRL Awards took place and Britney Spears was there to co-host the show along with Carson Daly. She received the first award ever, TRL's First Lady, beating Christina Aguilera, Avril Lavigne, Beyoncé, Shakira and Jennifer Lopez. Besides Britney, the only other artist that was there to accept their award, was Kevin Richardson from the Backstreet Boys. The winners were: First Lady – Britney Spears Evolution – Christina Aguilera Close Encounter – Blink 182 Free Ride – Mariah Carey’s “Loverboy” Hot Rod Sneak Attack – Backstreet Boys Best Live Performance – Justin Timberlake Biggest Frickin’ Star on TRL – Tom Cruise Most Revealing Moment – Adrian from No Doubt Gridlock – N Sync The Quit Your Day Job – Eve The Wet Your Pants – Jim Carrey Best Entrance – Verne Troyer Best Wringer – Adam Sandler Best :15 second human trailer – Brendan Fraser Most Incoherent Guest – Liam Gallagher Carson’s Most Uncomfortable Moment – Carson with an angry Backstreet Boys fan The TRL Top 10 from that show was: 10. Overprotected (Darkchild Remix) - Britney Spears 9. Uh Huh - B2K 8. Faith - Limp Bizkit 7. Love Don’t Cost A Thing - Jennifer Lopez 6. Pop - Nsync 5. Whenever, Wherever - Shakira 4. The Real Slim Shady - Eminem 3. Hot In Herre - Nelly 2. Genie In A Bottle - Christina Aguilera 1. Larger Than Life - Backstreet Boys