2003: Kiss on the Lips
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At the VMAs, Britney Spears was crooning and grooving alongside Christina Aguilera and Madonna, when the svelte Queen of Pop kissed her smack-dab on the lips. Madonna also went in for a kiss with Aguilera, but her smooch with Spears was all the media cared about.
Photo: © Reuters/CORBIS
2004: Gone to the Chapel
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Spears married Jason Alexander at the Vegas Little White Wedding Chapel before getting an annulment 55 hours later. According to Spears' rep, the whole affair was "a joke that went too far."
Photo: Splash News
2004: Barefoot Pit Stop
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At a gas station in Ventura, California, Spears—with then-fiancé Kevin Federline waiting in the car—entered a unisex bathroom completely barefoot, leaving the world to thoroughly question her hygiene habits. It was just one of several barefoot public restroom visits caught by cameras that year.
2005: Chaotic with K-Fed
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Despite all her more dramatic missteps, Spears has maintained that the worst move of her career was the five-episode, single-season reality show "Chaotic" with her then-husband K-Fed.
2006: Driving with Baby
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On the way to a Malibu Starbucks in her SUV, Britney was caught driving with Sean Preston, her infant son, on her lap and not in a car seat. She was torn apart in the press and was ultimately questioned by Los Angeles Department of Children and Family Services. Spears cited the paparazzi as the cause.
Photo: Ginsburg/Spaly/Splash News
2006: Baby Almost Falls
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A week after the car seat incident, Spears stumbled in Manhattan almost dropping son Sean Preston. His head thrust backward and his orange hat fell to the ground, but the baby was saved thanks to a quick reaction from a body guard. Her parenting skills were further scrutinized by the public.
Photo: St Clair/Winslow/Splash News
2006: On Air Breakdown
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"I'm an emotional wreck right now, " Britney blubbered on NBC's Dateline with Matt Lauer. Wearing a sheer baby doll top, denim mini skirt, and smacking on gum, Spears begged for the press to leave her alone.
2007: Making Bald Beautiful
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In 2007, Britney famously took an electric shaver to her blonde locks. Some tabloids said it was to avoid hair testing for hard-core drugs—she had spent a single night at a drug rehab facillity the evening prior—but Britney said otherwise. Following the incident at Esther's Haircutting Studio in California, a photographer asked why she shaved her head and Spears replied, "Because of you."
Photo: New York Daily News Archive / Contributor / Getty
2007: New Tats
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After shaving her head, Spears got two tattoos—a cross on her hip and a kiss on her wrist—at Body & Soul tattoo parlor in Sherman Oaks, CA. When a shocked Body & Soul employee asked Spears why she had shaved her head, she said, "I don't want anyone touching me. I'm tired of everybody touching me."
Photo: Helga Esteb / Shutterstock.com
2007: Umbrella Attack
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After her pleas for privacy, a still-bald Spears attacked a photographer's car with a green umbrella. She had just visited then-estranged husband Kevin Federline's home and was between stints in rehab. Her paparazzi attack became so famous that a Florida morning radio host even used photos from her breakdown on his "total nut jobs" billboards. The billboards were taken down after Britney's team threatened legal action.
Photo: Luis Santana / Splash News
2007: Running Red Lights
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In the middle of a very dramatic year, Spears was captured by the paparazzi recklessly driving. She ran a red light and made an illegal turn with her two sons in the back seat.
Photo: ©2003 Phil Ramey AGENCY/RameyPix/Corbis
2008: Custody Battles and Hospital Stays
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After another showdown with ex Federline—Spears refused to release their two sons to him—the police arrived at Spears' home. She was taken to the hospital for being under the influence of an unknown substance.
Photo: Hot Shots Worldwide
2008: Fights & Feet
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Later that year, the pop star got into a screaming fight with Sam Lutfi, her manager and friend, over paparazzo Adnan Ghalib. The feud ended with Britney sobbing, sitting on the curb in front of her home, barefoot, in denim hotpants, with her dog. One year later, Britney, seen here with Lutfi and Ghalib, took out restraining orders against both men.
Photo: ©2008 Phil Ramey/RameyPix/Corbis
2013: Quit over Poor Performance
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Spears said hasta la vista to the "X Factor" after rumors began to swirl that boss Simon Cowell was going to fire her for being "boring."
Photo: X Factor USA/Splash News/Corbis
2015: Twitter Feud
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Iggy Azalea fired off a tweet alluding to the fact that she blamed Britney for their "Pretty Girls" song collaboration failure. Even though she later claimed the tweet wasn't directed at her fellow singer and blamed the media for fanning flames, Spears didn't miss a beat and responded with a bit of cryptic shade.
Photo: Tinseltown / Shutterstock.com