Every Britney Spears Video: A Nostalgic Look Back

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At Celebuzz, today is a nostalgic type of day. Britney Spears first jived her way into our young, Total Request Live-watching hearts in the late ’90s when she was just a teen, and her we stand, waiting for  tonight’s “Hold It Against Me” premiere on MTV.

Our resident expert on Britney, music connossieur Becky Bain of Idolator, has followed Brit’s roller coaster career with an eagle eye these many years, forming an (often humorous) opinion of every music video that’s grounded in little known trivia. And if you have doubt about her commitment to the oft-maligned star, consider this true story, as recounted by Bain: “I received my first professional massage ever the day that Britney was hospitalized in January 2008, and I couldn’t relax because I was so worried about her.”

Celebuzz spoke with the Idolator pro as we relived all 30 Britney videos, from the good to the bad to the utterly amazing… Read on for Becky’s take on Britney’s video legacy.

“…Baby One More Time” – October 23, 1998, directed by Nigel Dick

Ah, where it all began. Britney arrived on the scene doing backflips and slinking around the hallways of her Catholic school exposing a coy charm, as well as her stomach. This song was an instant hit, the video dominated TRL for weeks – not to mention it was voted the #1 most iconic music video of all time on TRL’s final episode – and Britney’s midriff becomes a permanent fixture of her music videos from here on in.

“Sometimes” – April 30, 1999, directed by Nigel Dick

Sometimes, she runs, sometimes she cries, and sometimes she wears midriff-baring turtleneck sweaters during the Summer. Brit’s follow-up video was nowhere near as iconic as “Baby… One More Time”, but it’s hard to top a pop masterpiece.

“(You Drive Me) Crazy” – August 23, 1999, directed by Nigel Dick

Hey, look! It’s Melissa Joan Hart when she was still mainstream, and Adrian Grenier before he was! In just two videos, Britney went from suggestive schoolgirl to a confidently sexy young woman owning her sexuality.

“Born to Make You Happy” – November 27, 1999, directed by Billie Woodruff

Britney is clearly still working out the kinks in her style – another white turtleneck jumpsuit? Weirdly tailored rubber skirt? And orange tank top and khakis? Who was styling this video, Old Navy?

“From the Bottom of My Broken Heart” – December 15, 1999, directed by Gregory Dark

Britney packs up and leaves home – and her boyfriend – in this video for her ballad. The tone is on the serious side, but my favorite moment comes from Brit’s goofy faces while tossing around a football with her amour.

“Oops!… I Did It Again” – March 27, 2000, directed by Nigel Dick

Cheesy Titanic reference aside, if I ever get the chance to go into space, I’m doing it in a red latex catsuit. Although I nor anyone could wear it as well as Britney does in this video that looks like it was shot in an outer space-themed restaurant.

“Lucky” – July 7, 2000, directed by Dave Meyers

“Lucky” is Britney’s first foray into discussing the perils of fame in her songs. (Later examples include the videos for “Piece Of Me”, “If You Seek Amy”, and “Overprotected”.”) Brit plays two versions of herself in the vid – one, the omniscient narrator, and two, the stressed, overworked star. Both look pretty fantastic, even if she does wear a gorgeous cocktail dress over jeans at one point.

“Stronger” – November 13, 2000, directed by Joseph Kahn

Britney is so sizzling in this video, we bet even the chair is blushing.

“Don’t Let Me Be the Last to Know” – March 26, 2001, directed by Herb Ritts

I am so entranced by Britney’s cleavage in this video, you could tell me Brit was wearing clown face paint and a hat made out of waffles and I would just take your word for it.

“I’m a Slave 4 U” – September 24, 2001, directed by Francis Lawrence

You thought exposing her midriff was naughty? Ha! Britney releases her sexiest single to date, as well as a video filled with sweaty hot people crawling all over Ms. Spears as she makes orgasm sounds. And panties over pants? A trend is born!

“Overprotected” – March 12, 2002 (US), directed by Billie Woodruff

There were two videos made for this song – the album version had Brit and her pals dancing around an empty warehouse, but the more entertaining one was the Darkchild remix, which featured Spears prancing around a hotel wearing an outfit so garish (a hot pink bra under a poofy seafoam green mesh top) and ridiculous (a pair of oversized sleeves not attached to a shirt, matched with baby pink chaps over jeans), only Brit could make it look stylish.

“I’m Not a Girl, Not Yet a Woman” – February 5, 2002, directed by Wayne Isham

Britney is not a girl, not yet a woman, but definitely a mountain climber in this video for her ballad from Crossroads. Also, her pelvic bones are in full force here – I have never seen jeans pulled down so low and so tight.

“I Love Rock ‘n’ Roll” – May 28, 2002, directed by Chris Applebaum

Rock N Roll and Britney Spears don’t exactly overlap, but this video is worth it to see the pop star slink around the floor in a pair of leather pants and grind on top of a hog. Giddy-yup!

“Boys” – August 2, 2002, directed by David Meyers

I wish I could digitally remove Austin Powers from this otherwise entertaining video. Or at least fill Mike Myers with a more recent character so it doesn’t seem so dated. Jason Bourne? Batman? Honestly, anyone other than Austin Powers.

“Me Against the Music” – October 20, 2003, directed by Paul Hunter

Britney and her icon Madonna pair-up to prance around in their most fashionable masculine chic – Madge in a white suit holding a cane, and Brit in a collar-and-tie (no shirt necessary) – while chasing one another around. Although there’s some weird bisexual undertones – Brit about to smooch a disappearing Madonna at the end – it’s really all about the Queen of Pop publicly passing down the torch to her predecessor.

“Toxic” – January 12, 2004, directed by Joseph Kahn

Could this be the best Britney Spears video of all time? Quite possibly! It has it all: action! Sexiness! Blonde, redhead, and brunette Britney’s! There are so many excellent Halloween costumes in this one video alone. It also doesn’t hurt that the James Bond-inspired hook of this song is one of her best.

“Everytime” – May 17, 2004, directed by David LaChapelle

Britney appears to commit suicide in a bathtub after having a fight with her boyfriend in the video for this ballad – a bold move for the world’s biggest pop star at the time. Of course, she takes it all away – and soothes the nerves of angry parents calling it “irresponsible” to depict her own suicide – by waking up at the end and being “reincarnated.”

“Outrageous” – July 13, 2004, directed by Dave Meyers

This video may actually be the beginning of the middle dark chapter of Brit’s career. Spears hurt her knee while shooting the video with Snoop Dogg in New York, and had to undergo surgery. Because of her injury, the video was never fully finished, and her Onyx Hotel Tour was cut short.

“My Prerogative” – September 21, 2004, directed by Jake Nava

Britney covers Bobby Brown and pulls a “Jenny From The Block”, casting her real-life amour Kevin Federline in the clip, you know, because that’s always a fantastic idea. Why not just star in a reality show togeth— oh wait, they did that, too.

“Do Somethin'” – February 14, 2005, directed by Billie Woodruff and Britney Spears

“Somebody give me my truck so we can ride over clouds,” are the opening lyrics to this single, and lo and behold – Britney and her bevy of best gal pals are doing exactly that! TRIVIA: Using a Louis Vuitton pattern on the dashboard of her hot pink truck landed Team Brit a lawsuit by the designer, and he was awarded 80,000 Euros in damages. Plus he got the vid banned in Europe. Oops!

“Someday (I Will Understand)” – August 21, 2005, directed by Michael Haussman

Britney goes genuine for this ode to her unborn baby. At this point she still looks like a teenager herself, so it’s a little disconcerting seeing her with that huge belly, singing about motherhood.

“Gimme More” – September 25, 2007, directed by Jake Safarty

Britney filmed this striptease at the height of her post-Federline, post-head-shaving days, and the word is that she could barely sit still long enough to allow the crew to get enough coverage. Still, this is genuinely a good song.

“Piece of Me” – November 27, 2007, directed by Wayne Isham

Britney film this self-aware clip lampooning her real-life antics while criticizing the media for following Chris Crocker’s plea to LEAVE BRITNEY ALONE! It went on to sweep the 2008 MTV Video Music Awards.

“Break the Ice” – March 28, 2008, directed by Robert Hales

Team Spears decided to make an animated vid instead of something with Brit actually in it because she was to busy dealing with personal problems to dance in a sound stage for her next clip. It’s a clever idea to work around her, but I just wish the animation didn’t seem so cheaply produced.

“Womanizer” – September 28, 2008, directed by Joseph Kahn

What a difference a few hospital stays and a conservatorship makes! Britney is back in rare form for this sequel to the “Toxic” video, kicking off the pop parade of her new album, Circus. Which Brit do you like the best: office worker Britney with a Pulp Fiction-inspired black bob, sexy cocktail waitress redhead Britney, blonde limo driver Britney, or totally naked in a sauna Britney? My pick: all of them.

“Circus” – December 2, 2008, directed by Francis Lawrence

Britney – whose hair hasn’t looked this good since “Do Somethin'” – plays the ringleader in this sexy, old-timey-sideshow-inspired clip. And remember, the show must go on – but not without your Britney Spears perfume and your Bulgari diamond jewelry!

“If U Seek Amy” – March 10, 2009, directed by Jake Nava

As we saw in “Piece Of Me”, Britney isn’t afraid to poke fun of her own persona, and she does so brilliantly playing a bad-girl-gone-good (for the cameras) in the video for “If You Seek Amy”, a song created just so Britney could say the F-word in a song without really saying it. This video is the definition of “cheeky”.

“Radar” – July 22, 2009, directed by Dave Meyers

It hurts me to say this as we love this track – I even loved it the first time I heard it on Blackout – but this is maybe the most disappointing Britney video there is. The crossfade editing just make everything go that much slower, and no dancing sequence! Sorry, Brit, I say nay to this clip.

“3” – October 2, 2009, directed by Diane Martel

I like my Britney videos to have a narrative, even if that narrative is “I’m a super spy, and now I’m a redhead, and now I’m an office worker, and I’m kicking ass!” So this music video is on the boring side. Plus, shouldn’t there have been only 2 backup dancers, making it three people? It could have been Brit’s version of “Single Ladies”! And then a fourth sexy lady or man could come out during the bridge, and it’d be super hot and connected to the song. At least Brit looks fit and most importantly, happy.

Which one is Britney’s all-time best? Tell us in the comments section.