There aren’t many celebrities out there who have had a more interesting life than Britney Spears. Whether it’s turning heads with her good looks, because of controversy, or because of controversy around her good looks; she is easily considered to be one of the biggest celebrities of all-time.
Below we have the 10 hottest moments of Britney’s career, such as showing off in various sexy outfits in concert, music videos, on the beach or that infamous moment with Madonna.
But don’t think Spears gets off lucky because we’ve also tracked down 10 of the worst moments and looks of her career.
However thankfully for Spears, as you’ll learn from our list, she may never be looking sexier than she does right now!
20. Does – Her Appearance On HIMYM
Britney Spears looks amazing in the various outfits that she wears in her music videos, but she has also found herself plenty of success as an actress. Perhaps most prominently, Spears appeared in several episodes of How I Met Your Mother, including doing some booty bumping with Barney Stinson. At the time, Spears’ appearance in the series brought in the highest ratings.
Spears also earned critical praise for her performance in the movie Crossroads which was released in 2002 and earned $60+ million off of their $12 million budget.
We’re sure you wouldn’t hate seeing Spears on your television on a regular basis!
19. Doesn’t – The Head Shave
Britney Spears was not having a strong week in 2007 (okay, more than just a week!). Her aunt had recently passed away from ovarian cancer and as a result of this, Spears found herself in drug rehabilitation (though she left after only a day).
Following this, Spears elected to shave off her head! The owner of the hair salon, Esther Tognozzi broke down what happened,
“She sat in my chair and said, ‘I want my hair shaved off.’ I said well I’m not doing it, Of course, I tried to talk her out of it, I said, ‘You know maybe you’re having a hormonal moment or something, and maybe tomorrow you’ll feel differently about it. Let’s talk about this.'”
But Tognozzi said that when she was talking to Spears’ bodyguard, she went for the buzzer and shaved it all off!
18. Does – When She Was At The Super Bowl
If you were watching the Super Bowl back in 2001, unfortunately, you were not treated to a very good game as the Baltimore Ravens knocked off the New York Giants, 34-7.
One of the highlights of the show then, especially if you were a Giants fan may have been getting to see Spears rock out during the halftime show alongside Aerosmith. Especially when you can clearly see that Spears was doing all she could to score with her look!
Spears was also interviewed back in August after her studio album Glory was released which led to her mentioning how she would probably be up to performing the halftime show in the near future.
17. Doesn’t: The Umbrella Incident
There are several moments from Britney’s 2007 that are worth touching on, and the year would not have been complete without an incident in February when she elected to attack a paparazzi’s car with an umbrella.
When talking about the incident, Spears tried to explain it off as being part of a movie role (what?),
“I apologize to the pap for a stunt that was done 4 months ago regarding an umbrella. I was preparing my character for a role in a movie where the husband never plays his part so they switch places accidentally. I take all my roles very seriously and got a little carried away. Unfortunately I didn’t get the part.”
Quick, does anyone know any movie that features some serious umbrella attacking? To make the story all the sadder, the incident happened following a visit with her estranged husband, Kevin Federline.
16. Does – When She, Beyonce, and Pink Became Gladiators For Pepsi
Britney Spears is an outstanding musician and performer, but she is also an incredibly smart businesswoman who has managed to have several lucrative endorsement deals.
Spears signed a contract with Pepsi back in 2001 to the tune of $7-8 million, which at the time was their highest promotional deal.
When talking about the deal, Spears said “It’s such an honor. I’m a big fan of Pepsi products and Pepsi commercials.”
15. Doesn’t – Partying With Paris
There was a time in Britney’s life where she was so stressed out with everything that she elected on several occasions to get her party on with Paris Hilton. Which, to be honest, if anyone knows how to party, at least we’d say Hilton has plenty of experience. The problem is that if one of these ladies entered into a club it would cause pandemonium, much less both of them!
The above photo of her valley girling out HARD is still an embarrassing one nevertheless.
While the two haven’t partied it up a while, Hilton did share a throwback photo of the two of them on Instagram back in December.
14. Does – Britney’s Back (In A Bikini!)
Britney Spears looks absolutely stunning whenever she steps on stage (something you’ll absolutely learn) but we’d be foolish if we didn’t take a moment in this list to point out how amazing she can also look when soaking up the sun.
The photo that you’re looking at was taken of Spears back in August 2016 when she was enjoying a vacation in Hawaii. While Britney has been open in the past about how much she loves going on vacation with her family, we are sure she definitely didn’t mind taking some time on this day to enjoy the sun by herself.
Especially when there are photos from later that day from when Spears elected to leave her swimsuit top off to the side!
13. Doesn’t – The Weight Gain
Britney Spears is no stranger to people attacking her for the decisions she has made with her body, so naturally, when she put on some weight the media was quick to attack her.
Spears is not the only celebrity that has “struggled” with weight gain and defended Kim Kardashian who was also getting attacked back in 2013 during her pregnancy,
“I remember that time… That should be the time when your body is most treasured. I loved being pregnant for so many reasons, not to mention the sex is awesome then.”
Spears was also criticized in 2015 after the above photos emerged of her and Iggy Azalea with Spears looking less than flattering.
12. Does – The Kiss
Britney Spears has had plenty of performances in which she has gotten all up over her male and female backup dancers, but her most memorable on-stage kiss is always going to be back in 2003. But granted when you are locking lips with Madonna, who then decided to kiss Christina Aguilera, you have to understand that it’s a pretty high bar to reach.
When interviewed about the kiss, Spears admitted that she had never kissed a woman before and that it was spontaneous and while she wouldn’t kiss another woman; she’d have no problem locking lips with Madonna again.
It may be over a decade later, but something tells us if it happened again it would be an even bigger story.
11. Doesn’t – Her Relationship With Alexander
Everyone has that relationship that they would rather erase from their memory bank. That becomes significantly harder if you’re famous and even harder if that relationship ends in marriage. Yet back in 2004, Spears blew up the headlines when it came out that she had married her childhood friend, Jason Allen Alexander in Vegas.
To make the story all the weirder, Spears and Alexander’s marriage was annulled 55 hours later (something Ross and Rachel could have taken a hint from, just saying!).
When talking about the marriage, Alexander said,
“It was just crazy, man…we were just looking at each other and said, ‘Let’s do something wild, crazy. Let’s go get married, just for the hell of it.’”
It was confirmed that neither of them was intoxicated at the time.
10. Does – Relaxing With Tinashe In Slumber Party
When it comes to having a slumber party, you can imagine Britney Spears and Tinashe are two women that you would make sure to invite. While Tinashe is still a growing star in the industry, one way to gain some great exposure is to be featured on a Spears song and to appear in the video wearing essentially nothing at all!
The song “Slumber Party” was released by Spears back in November and featured her and Tinashe getting into plenty of steamy situations as well as getting all up and personal with one another. It was the 2nd single to be released from Spears’ 9th studio album which was released back in August.
The song has already been viewed more than 59 million times on YouTube and we wouldn’t blame you if you decided to go and pull up the video when you were finished with our list!
9. Doesn’t – When She Pissed Off PETA
Britney Spears was perhaps looking her best when she stepped on stage in 2001 for the MTV Video Music Awards. And while she’d love you to only remember how good she looked, the performance will forever be marred by her decision to drape an albino python over her shoulders.
PETA (understandably) was the most vocal and the controversy around the situation and ended up canceling an anti-fur billboard that was going to be put on featuring Spears.
Spears talked bout the incident in 2016 to E! News, saying,
“It’s insane! Why did I do that?,” Spears was then asked if she would ever repeat her decision, leading her to say,, “Hell, no! It’s so dumb. No! Never!”
8. Does – Her First Ever Tour
While it’s true that Britney Spears received some criticism for the racy outfits she wore during her …Baby One More Time tour, it’s hard to consider her first ever tour to be anything but a huge success. The show ran from June 28th, 1999 until September 15th, 1999 and consisted of 56 shows. This was followed by another tour in March 2000 that Spears used to help promote her second album which was also a huge success.
Love or hate her, can you imagine getting to say you saw Britney Spears way back in 1999?
Spears also worked diligently with the fashion designer and people behind the scenes to make sure she had an active part in helping create the overall image of what she wanted her first tour to look like.
7. Doesn’t – When She Endangered Her Baby
The paparazzi was not giving Britney any breaks back in 2006 and were often hounding her every time she went out. You can imagine this gets incredibly tiring, especially if you’re out trying to enjoy your day with your son.
Unfortunately for Britney, when she elected to try and escape some angry paparazzi she decided to put her then 4-month-old son on her lap instead of in the car seat in the back.
This is incredibly dangerous and would cause concern to begin with, much less when it was Britney doing it.
Britney released a statement on the matter saying,
“I was terrified that this time the physically aggressive paparazzi would put both me and my baby in danger. I instinctively took measures to get my baby and me out of harm’s way, but the paparazzi continued to stalk us. I love my child and would do anything to protect him.”
Hate to break it to you Britney, but your instincts here did the opposite of putting him out of harm’s way!
6. Does – Her Lingerie Line
Britney Spears has spent most of her career with men fantasizing about what she would look like in some lingerie. Well, you’re in luck because back in 2014, Spears debuted her own brand of Lingerie and you better believe she was one of the models!
When talking about why she designed the line, Spears said,
“I’m a mom, so I’m really busy cleaning up poop and all those kinds of things — from dogs and kids. So I think it’s important for us women to make that special time for ourselves, to feel sexy and make an effort to light the candles and put on something really beautiful for ourselves.”
It’s clear that if Spears ever wanted to step away from the music industry that she would be fantastic as a lingerie model!
5. Doesn’t – The Controversy Around Sexy Rolling Stone
Britney Spears definitely started working her sexuality more as she got older and by 1999, at 19 years old, she was clearly comfortable showing off plenty of skin to the world. The above photo was taken for Rolling Stone and garnered some serious hate from the American Family Association who said, “[It was] a disturbing mix of childhood innocence and adult sexuality,” as well as asking, “God-loving Americans to boycott stores selling Britney’s albums.”
Spears was quick to defend herself saying, “What’s the big deal? I have strong morals. […] I’d do it again. I thought the pictures were fine. And I was tired of being compared to Debbie Gibson and all of this bubblegum pop all the time.”
4. Does – Her Vegas Performances
Britney Spears has had herself plenty of critics throughout her career, but there aren’t many people hating on the amazing shape that she has gotten herself in for her Las Vegas shows.
Spears shed some serious pounds prior to her residency and did so with the help of personal trainer Tony Martinez; who opened up about her goals, “She loves all core workouts. She’s a very tenacious woman. She wants to get it done and get it done right.”
It’s clear that her efforts have led to some impressive results, which we’re sure she is grateful for when you consider it’s no easy feat to put on a concert on a regular basis!
3. Doesn’t: Her Marriage To K-Fed
Britney Spears, unfortunately, has had several prominent relationships that could be on this list. Her most “successful” was the marriage to Kevin Federline that lasted from July 2004 until July 2007.
The relationship was criticized by media from the start as the two got engaged after only 3 months, and Federline had another baby on the way with another woman.
One year after the divorce, Spears spoke out saying “I think I married for the wrong reasons. Instead of following my heart and doing something that made me really happy, I just did it for the idea of everything.”
2. Does – Baby One More Time And I’m A Slave 4 U Videos
When MuchMusic (which sadly used to be a much bigger thing) put together their list of sexiest music videos, “I’m a Slave 4 U” came in at #1, so how do we not include it in our list? Considering it was off of her 3rd album, it is clear that by this point in her career Spears knew just how sexy she was.
The song isn’t free of controversy, as it was what she was singing in the performance involving a snake back in 2001 which you now know more about.
We’re sure you also aren’t complaining that we decided to include a photo from “Baby One More Time” which features Spears dressed as a school girl and was part of what helped make her such a big star.
1. Doesn’t – When She Seriously Injured Her Knee With Snoop
Britney Spears must have thought her music video for the song “Outrageous” was going to be super awesome. After all, she even had Snoop Dogg appear in it!
Sadly for Britney, it was filming this music video that Britney underwent a significant knee injury while performing a dance move. The result was arthroscopic surgery and 8-12 weeks of rehabilitation.
On top of this, Britney had to have her remaining shows for The Onyx Hotel Tour get canceled.
If there was one benefit from this situation, it may be that this incident also led to the song getting dropped as the theme song for Catwoman.