1. “Baby One More Time”
The video that started it all! In this controversial debut, Britney established her image as a teen provocateur with a strong Lolita vibe. The video constantly cuts between her sexily dancing in a high school hallway with her navel exposed to pouting like an innocent deer against a locker which set the foundation for her good girl/bad girl persona. Teasing the audience and giving them what they couldn’t have was Britney’s forte and nothing exemplifies it more than this delicious slice of barely legal American pie. Also, who can resist hearing the beginning of her unique vocal stylings? “The reason I breath-UH is you-UH.” UH, indeed!
Britney’s ballads are usually a total snoozefest but what the song “Sometimes” lacks, the video makes up for in amazingly bad ’90s fashion and synchronized dancing. Leave it to Britney to take an ultra conservative all-white ensemble (with a turtleneck, for Christ’s sake!) and be like “abracadabra, slutty!” by removing the bottom portion of the shirt and exposing her midriff. Thank god the clothes are intriguing because the actual plot of this video is paper-thin. Britney’s lusting over this guy on the beach (and creepily spying on him via telescope) but she’s too scared to make a move. So instead of actually talking to him, she just dances with a bunch of strangers, who are also conveniently wearing all white, on a pier. What’s interesting about this video is that it doesn’t end with Britney getting the guy. She just gives up and is like “whatevs. let’s get a coke, y’all!” This is the first and possibly last time a video doesn’t end with Britney getting laid.
3. “(You Drive Me) Crazy”
Even though the single “Baby One More Time” was true pop song brilliance, the rest of the record blew donkey balls. None of the hooks were memorable, the production sounded cheap, and there were too many ballads, which is a sin for any Britney record. Luckily, Britney (or her management) realized this and were like “Um, we need to re-record the next single so it doesn’t suck so hard.” And thank god they did because “(You Drive Me) Crazy” is one of my favorite Britney songs and videos. It was released in tandem with that awful eyesore Melissa Joan Hart flick of the same name and unfortunately, she had to make a cameo in this to promote her crappy movie. But not even Melissa Joan Hart and her severe lazy eye can ruin the video. It’s that good! In it, Britney plays an oppressed waitress who works at a 1950s-style diner and just wants to slut it up and have some fun after work. She changes into a signature navel-baring shimmery green top and low-rise black pants and dances around chairs while watching people breakdance. Since Melissa Joan Hart can’t dance or do anything cool, she’s relegated to hanging out with Adrien Grenier and taking shots in some isolated corner.
4. “From The Bottom Of My Broken Heart”
This video is the last from her debut album and undeniably the weakest offering. Even Nigel Dick—Britney’s collaborator on her first three music videos—didn’t want to direct a video for this insufferable ballad and handed the reigns over to Gregory Dark, a dude who previously directed porn. I don’t even really know what it’s supposed to be about. Britney’s leaving her small town of Cedar Rapids—we can only guess as to why but my hunch is either rehab or college—and has to say goodbye to her boyfriend who’s not even that cute! To make matters worse, they put her in all of these dowdy hats and dorky clothing. I didn’t even see her bellybutton once and if Britney’s stomach doesn’t make a cameo in a video, you know it’s not good.
5. “Oops…I Did It Again”
At this point, the music video for “Oops…I Did It Again” has become almost as iconic as “Baby One More Time.” That red latex bodysuit, the gratuitous shots of Britney’s lip gloss, and the cheesy Titanic-inspired dialogue all help make this video a guaranteed replay on YouTube years later. The plot is sort of hilarious. An astronaut goes to Mars and stumbles upon the Queen (Britney obvs) who apparently is some sort of femme fatale. She’s not that innocent! She breaks hearts! And of course it wouldn’t be a Britney video without an all white outfit that exposes her navel! What is up with her wearing revealing white clothing all the time? Oh, I get it. Because white symbolizes chastity and Brit loved to keep ’em guessing. I’m so glad I went to a liberal arts school, you guys.
“Lucky” was Britney’s most ambitious song and video concept yet. In it, she plays a successful actress named (you guessed it!) Lucky who, by all appearances, looks like she has everything she could possibly want but, in actuality, is super sad and lonely! Britney plays two roles in this one: Lucky, the celebrity, and Lucky, the ghost of her former self. Because the old Lucky has died, you see. It’s been killed by the cruelty of Hollywood! And she might not be as chic as the celebrity version of herself but, much like the real Britney, Lucky the ghost has never met a belly shirt she didn’t like! So thank god for that! Thank god you can be dead and still have the good sense to bare your midriff!
Gasp! This video opens up with Britney running into her ex at a party with another woman. “Whatever,” Brit says with all of the conviction of a rice cake before running fast into the arms of a metal chair. She proceeds to spend the rest of the video alternating between dry humping the chair and throwing it around like a rag doll. At some point, there’s also an unexpected rainstorm, which conveniently drenches Britney and her gothic clothing to the point of transparency. If being strong involves wearing a ton of black lace, consider Britney Spears to be the heavyweight champion of the world.
8. “Don’t Let Me Be The Last To Know”
This is undoubtedly Britney’s sexiest outing yet. Although her previous videos have included the occasional love interest, they never went further than giving each other pensive stares. In “Don’t Let Me Be The Last To Know”, however, Britney straight-up macks on some shirtless guy with tan lines and an amazing ass on a beach somewhere. Wearing nothing but a bikini top and denim cutoffs, Britney spends most of the video rubbing her tits in confusion and straddling a tree. The whole thing is very “Wicked Game” by Chris Issak except with way more lip gloss.
9. “I’m A Slave 4 U”
Britney Spears’ third album, Britney, marked a departure from her usual brand of Swedish bubblegum pop in favor of a grittier urban sound. “I’m A Slave 4 U”, the record’s first single, was produced by The Neptunes and features Britney cursing and at times even panting! I’m not sure what the plot for this video is but I have a feeling it has to do with global warming. Britney and her band of dancers are victims of what seems to be a terrible drought and to get through it, they’re forced to lick each other’s faces and lay on top of each other. Towards the end, there’s finally some rainfall but at that point, Britney is too horny to cool down and just continues to dance!
There comes a point in every pop star’s career where they have to make a song about the downfalls of fame. Somewhere in their contract, there must be a clause that says, “After I achieve some modicum of success, I must sing about how that success is bringing me down.” Britney already tackled the subject using a fake celerity named Lucky but with “Overprotected”, she ditches the thinly veiled character and puts herself at the forefront. The video opens up with Britney getting bombarded with paparazzi as she sings/talks “I need time, space, love…I need me!” She then escapes to what looks like an abandoned warehouse and hangs out with her music video BFF’s: a chair and some backup dancers. Um, quick question: why is she always hanging out with a chair? If there’s some symbolism there, it’s lost on me. The rest of the video is pretty weak. Britney makes sad faces at the camera and attempts to dance through the pain. Meh. “Lucky” was a lot better.
10. “I’m Not A Girl, Not Yet A Woman”
I’ll admit that this not my favorite phase of Britney’s career. You could just tell she was 1.5 albums away from going batshit insane and her transition to a more adult sound feels belabored to say the least. “I’m Not A Girl, Not Yet A Woman” is a crappy ballad that was tied into her dismally mediocre movie, Crossroads. Did anyone see that BS? It wasn’t even “so bad, it’s good!” a la Showgirls. It was just bad. More than that, it was boring! Unsurprisingly, the music video for this is also a total bore. The only thing keeping me captivated is watching Britney’s low rise jeans. Half an inch lower and we’d get to see something we would later witness in paparazzi photos of her hanging out with Paris Hilton.