She’s had a tumultuous life, but Britney has always remained close with her family. When Jamie Lynn was pregnant at the young age of sixteen, Britney stuck by her side. She also bought her brother, Bryan, a 1.5 million dollar loft in New York City, but then nearly burnt it to the ground when she knocked over a candle.
Spears has always been generous with her money – after September 11th, she donated a million dollars to the children of uniformed officers affected by the attack.
Britney Does Things her Way
As she toured, promoted, and recorded, Britney didn't have much time to write her own lyrics. She had a stable of writers to help her out there, so it wasn't until her third album that she started to provide her own material. Leave it to Britney to create her own unique way of keeping track of the lyrics she came up with.
She would call her house phone from her cellphone and leave a message on her own answering machine, singing through the phone to make a recording for herself. Not only did it keep the ideas from disappearing, but she had a recording to transport with ease. One of the first songs Spears created in this way was “Not a Girl, Not Yet a Woman.”
Following in Her Grandmother's Footsteps
In 2002, Spears decided to right by her great-grandmother, opening her own restaurant in New York City. The restaurant bore the title Nyla, and it sold Louisiana-style Cajun food, the same thing that Spears enjoyed every day while growing up. Only months after it opened, it crashed, and Spears came away saying her business partners hadn't kept her involved.
Unfortunately, the restaurant took on a huge amount of debt, and health code violations plagued the establishment. When Spears pulled out, the location closed and rebranded as an Italian restaurant before closing permanently.
The Devil Met her at the Crossroads
Spears had done almost everything right and had become one of the most famous stars in the world after mere years. Though it seemed like she could do it all, that came back to bite her when she starred in a movie titled, fittingly, "Crossroads." As a coming-of-age road trip with a few other female stars, it should have drawn in plenty of box office sales.
And it did...but critics hated it, taking aim at Spears's acting and calling it nothing more than a vanity project. Zoe Saldana, of all people, called Spears's acting “very good.” At the same time, Britney's parents revealed they were divorcing after twenty-seven years of marriage.
The Kiss That Shocked the World
The 2003 VMAs featured an incredible anticipated performance that combined Madonna, Britney, and Christina Aguilera. Britney found a way to make the performance even more memorable. During the middle of Madonna's classic pop hit “Like A Virgin,” the queen of pop kissed both fellow performers on the lips (no doubt inspiring Katy Perry in the process).
This memorable event came right on the heels of Britney's breakup with Timberlake. While Madonna quickly switched sides to give Aguilera the same lip lovin', the broadcast quickly pointed the camera at Timberlake, catching him in the process of making a face.