Kim Kardashian has been in the spotlight for more than a decade. Before curating her billion-dollar empire, the mogul went through a series of unfortunate and awkward moments that will now stay with her forever, as well as her Hollywood résumé. As she climbed her way to the top, Kim Kardashian even tried releasing a single and had a part in a feature film.

She might have an estimated 1.4 billion net worth, but her fortune came after trying various ways to shine in the Hollywood spotlight. Now 42, the reality star is one of the most talked-about celebrities in show business.

Before becoming a total reality star, Kim went through different eras trying out a singing and dancing career, as well as a role on the big screen.

Reality Titbit has gathered Kim Kardashian’s most bizarre (but also cringey) moments.

Kim Kardashian’s list of awkward moments – single to concert stage

5. Yes, Kim Kardashian released a single

The Kardashians are very talented in many ways, but singing is not one of their best attributes. Still, that didn’t stop Kim Kardashian from trying and releasing a single.

In 2011, the reality star released her song Jam (Turn It Up). Believe it or not, the single peaked at number 17 on the US Billboard 100 charts.

“That’s like the one thing I can’t believe I did that,” she told Andy Cohen. “You know what, we donated our money to a cancer organization.”

Although it wasn’t one of her best business move, the reality star admits it was “so much fun”. Her sisters, Khloé and Kourtney, defended her later, saying Kim wasn’t ‘trying to be Mariah Carey’.

4. A twerking moment on Dancing With The Stars

Before her shot in the music industry, Kim gave it a go on the dance floor. In 2008, she was paired up with professional dancer Mark Ballas. Kim Kardashian participated in season seven of Dancing With The Stars.

Even though the couple were eliminated on week three, the mom-of-four gave her everything – and even showed off some twerking moves to her partner.

Sharing her short experience, Kim later said she felt like an ‘i****’ and it had been the ‘worst’ time, reported the Daily Mail.

In April 2021, Khloé took fans back in time with a picture of Kim during her famous dancing era. It came after she confessed to not knowing how to dance after TikToker Addison Rae gave her and her former best friend Kourtney a lesson.

3. A feature in the ‘Disaster’ movie

2008 was the year of trying new things and exploring different career paths. In the parody film Disaster Movie, Kim had the role of a character named Lisa. Kim’s feature in the film leads to her character being killed by a meteor.

Sharing her experience with ABC’s Big Fan, Kim didn’t have many good memories from her three-second appearance, apparently.

“I’m mortified if you have the clip,” she said.

Later in 2018, Kim and her sister Kendall Jenner made a short appearance in the comedy film Ocean’s Eight. The two siblings didn’t have any lines and only walked to the stairs, recreating the annual Met Gala.

2. Flour-bombed during her perfume launch

Not everyone loves Kim Kardashian. Ten years ago, during the launch of her perfume True Reflection at The London Hotel in West Hollywood, a shocking scenario happened in front of the cameras.

At the time of the incident, she approached a camera to answer a few questions. Moments later, an intruder, who turned out to be a PETA protester, ran up to her and threw a flour bomb at her back.

The incident was dealt with professionally, with Kim immediately leaving the red carpet. An episode of Keeping Up With The Kardashians showed when Kim decided to change and return to the event.

Speaking afterward to the cameras, she said: “That probably is the craziest, unexpected, weird thing that ever happened to me”.

1. Prince telling her to ‘get off the stage’

In 2011, Prince performed at Madison Square Garden in New York City as part of his Welcome 2 Tour.

During one of his performances, Prince invited Kim to get on stage with him to show some dance moves. Knowing her past trials in DWTS and her Turn It Up era, she knew she wasn’t the best candidate to do so.

Naturally, the mogul failed to do some dance moves and only clapped her hands. It was then that the singer got angry and expressed his disappointment towards the star by kicking her off the stage.

“Get off my stage,” he said into the microphone.

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