Awkward Britney Spears Moments That Were Caught On Camera

Only after a documentary called "Framing Britney Spears" aired in 2021 did the world begin to understand the personal torment the megastar had endured while living under a legal conservatorship. The situation of nearly 14 years, which placed her father in control of virtually every aspect of her life, occurred after her infamous head-shaving incident in 2007. Paparazzi shots of the incident (including her subsequent attack on a photographer's car with an umbrella) became the symbol for Spears' undoing and ultimately resulted in the legal maneuver that placed her life under her father's control.

Many years later, concerned fans began to question the continued existence of the conservatorship and started speaking up for Spears. Supporters staged protests and insisted the courts revisit the agreement. Thus, the now-famous "Free Britney" movement was born — allowing the world to learn of the singer's plight. Finally ending in November 2021, Spears has regained control of her life and appears to be thriving.

Considering that Spears' domination of pop music came just after the rise of the Internet, as such, nearly her every moment, both public and private, has been documented for the world to see. In the course of a wildly successful career spanning multiple decades, the good, the bad, and the ugly are bound to be captured and broadcast to the world. Some moments, however, don't fall into the aforementioned categories and are merely just plain awkward.

Britney Spears appeared on "The Ellen DeGeneres Show" in October 2018 to share what was billed as a "big announcement." Unfortunately, the short chat with DeGeneres didn't yield much information. Essentially, the star "announced" she would make a "big announcement" on October 18. DeGeneres, slightly befuddled, offered to host the mysterious event on her livestream. Viewers tuned in later that month to watch an enthusiastic Kalen Allen give a play-by-play of "the announcement" on behalf of "The Ellen DeGeneres Show." 

After several minutes of hype, clips of Spears' hit songs begin blasting as the exterior of the Park MGM Hotel in Las Vegas lit up with video images relating to her career. Eventually, a graphic announcing her upcoming "Domination" residency comes into focus. Spears then appears at the top of a black staircase amid a fanfare of smoke, music, and fireworks. Looking a bit confused, she waves a couple of times, looks around, and stands there for a minute before she descends the staircase to the red carpet below. Once there, she walks toward a multitude of fans who have come to witness the spectacle. She signs some autographs and approaches Allen who, strangely, is no longer holding a mic. The two have some interaction for mere seconds (that cannot be heard) after which she jumps into an SUV and departs.

Needless to say, the whole affair was a bit confusing for everyone who witnessed it.

The term "wardrobe malfunction" became a thing after Justin Timberlake used the term to describe the gaffe that occurred during his 2004 Super Bowl halftime performance with Janet Jackson when her breast was revealed on live television. Since its inception, the expression has been used to describe any similar event that occurs in front of an audience. Having performed thousands of live concerts in her career, Britney Spears is no stranger to such incidents. Fortunately, they don't happen every day, but during one performance in 2016, Spears experienced two separate incidents in which her garments failed her (per Entertainment Tonight).

That particular evening, during her version of Joan Jett's "I Love Rock and Roll," the bra-like top she wore appeared to snap at the neck. As she struggled to reconnect the strap, a backup dancer came to her rescue and reattached it only to have it fail again seconds later. It should come as no surprise that Spears never missed a beat during the mishap. Later that same night, Spears wore a cropped denim top when something underneath it appeared to come loose, exposing her once again. The singer took it in stride, however, as a backup dancer gave her his own shirt (via Entertainment Tonight).

The fact she appeared unfazed both times and powered through her performances just proves she's a pro.

Imagine not recognizing Britney Spears. That's exactly what happened to actor and "Modern Family" star Ed O'Neill when he was approached by the singer at the airport while he waited to board a flight to Hawaii. He shared the story of the amusing encounter with Ellen DeGeneres on "The Ellen DeGeneres Show" in 2018. As he tells it, he was getting up to board the airplane when a woman approached him wanting a picture with him. He told DeGeneres that he didn't recognize her, but that she seemed nice, so he happily complied and took the photo. The singer later posted it to her Twitter account with the caption, "Fancy running into this guy! Such a sweetheart!!" The photo features a giddy-looking Spears seated on the arm of O'Neill's chair. His expression is notably less enthusiastic. 

The former "Married ... With Children" star admitted to DeGeneres that he had no idea he had just crossed paths with one of the world's biggest stars. Only after his manager revealed the woman's identity and told him that the photo had gotten 53,000 likes did he learn her identity. Spears is in good company, however, because, during that same interview, O'Neill shared how he also failed to recognize Taylor Swift when she approached him at a birthday party for a cast member of his.

As with many singers, Britney Spears generates income from more than just her concert tours. According to The Hollywood Reporter, her first fragrance deal back in 2004 earned her over $50 million. The perfume, "Curious," released by Elizabeth Arden, was a smash success, selling over 700 million units. Spears followed up with a second scent, "Fantasy," which was also wildly popular, earning the singer over $30 million in the first three weeks alone. 

Spears later launched a lingerie line called "The Intimate" that she designed herself. Describing the lingerie line in 2014, the singer said, "Every woman should feel confident and beautiful in everything she puts on. My vision for The Intimate Britney Spears is to create pieces that are sexy, luxurious, and comfortable at the same time" (per PopSugar). During a promotional event in Denmark, Spears was on hand to talk about her newest business venture. There, she was captured on camera numerous times making awkward facial expressions (per the Daily Mail). Interestingly, upon scrolling through the photos, you couldn't help but notice that nearly all featured her with forced-looking grins. The Daily Mail surmised that fatigue from travel or her recent breakup might have been behind the star's goofy faces.

One of the Hollywood relationships that defined the early 2000s is that of Britney Spears and Kevin Federline. "I met her at a club in Hollywood, Joseph's. Our eyes met and that was it. We just hit it off right away. I learned real fast how much of a whirlwind the press and everything was," Federline described of the first time he met Spears (per People). One thing that resulted from the couple's tumultuous time together was their own video documentation of it in a series that aired on UPN in 2005. "Britney & Kevin: Chaotic" consisted of five episodes of amateurish video in which the couple revealed aspects of their relationship before and after getting married (per IMDb).

Looking back on the project several years later, Spears told The Telegraph (via Digital Spy), "I would never do something like that again." She added, "Actually, that was really bad. That was probably the worst thing I've done in my career." The couple, who married in 2004 — this was pre-conservatorship and, undoubtedly, a much more carefree period of her life — later split in late 2006 and officially divorced in 2007 (per People). In a career that has weathered numerous awkward moments, Spears' identification of the television series as her worst career move ever is certainly eye-opening.