Walters also grilled Kim about the X-rated tape she made with hip-hop star Ray-J in 2007 that helped launch her into the spotlight.
Tough questions: Barbara Walters grilled the Kardashians after including the family on her 10 Most Fascinating People of 2011 list
Grilling: Kim was asked about the 2007 sex tape that helped to make her famous
It proved to be an awkward moment, with Kim clearly a little rattled at being caught off guard.
'Whatever you do, you might think...' Kim, 31, she stammered, trailing off.
She then said: 'I've made mistakes in my life for sure.'
Her mother and manager quickly went into damage control mode, offering to Kim: 'You learned a lot from that.'
Jenner went on to describe the experience as 'devastating' for the family, adding that she cried herself to sleep at night over it.
'No talent': Walters took a swipe at the famous for being famous reality TV family
Awkward moment: Kim was almost lost for words when she was asked about this X-rated tape
'You don't really act; you don't sing; you don't dance,' Walters said.
'You don't have any - forgive me - any talent!'
Khloe was the first to chime in, saying: 'We're still entertaining people.'
'I think it's more of a challenge for you to go on a reality show, and get people to fall in love with you for being you,' Kim mused.
Then Khloe added: 'None of us think we have talent. none of us think we can sing or act or dance.'
Khloe was also asked about criticism she has received on the internet, with some cruelly comparing her to Shrek and called an ogre.
'The Internet can be so negative... I’m over it now, I own who I am, and I have the best husband of in the world,' she said.
Khloe and her husband Lamar Odom are now set to move states after his transfer to the Dallas Mavericks.
Apple owner Steve Jobs, who died in October at 56, topped the list while Amanda Knox, Herman Cain, Donald Trump, Derek Jeter, Simon Cowell, Modern Family stars Eric Stonestreet and Jesse Tyler Ferguson, Pippa Middleton and Katy Perry were also included.