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The judges of X Factor known for being feisty, the TV mogul even called her a brat on one of the interviews.
And it was no different on the Conan O'Brien show on Monday night when both Simon Cowell and Demi Lovato guest on the late night talk program.
In their interview, the fiery 19-year-old Disney star even makes fun of Cowell by calling him an '***hole' on live television.
The whole thing started when host Conan asked Demi for her view on Simon's obligatory tight white T-shirts.
The singer and actress took the opportunity to make a light-hearted joke about the 52-year-old's 'man cleavage'.
'We're trying to reach a younger demographic, and I don't feel we're going to accomplish that when he's showing more cleavage than Britney [Spears] and I are,' she said.
Simon then answered that the best solution to the problem would be for her and Britney to show more cleavage, to which Demi replied: 'I'm good. Thank you!'
The acid-tongued TV mogul then claimed that his T-shirt protected his modesty, but Demi wouldn't let up with her verbal tongue lashing.
'I'm surprised, because normally you could braid your chest hair,' she said.
Simon then begged Conan to interfere: 'Tell her to stop picking on me, please,' he whined.
'Don't pick on him! He's a kind man who's NEVER insulted anyone!' Conan said in a sarcastic tone.
Afterwards, the talk show host them went on the ask Simon why he often refers to Demi as 'annoying'.
The Syco boss then looked at Demi before asking: 'You are very annoying. How's that?'
Demi then answered: How's that? You can be a bit of a**hole! How's that?'
On TV, Simon may be known for being Mr. Nasty, but on his recent late night TV interviews, he was more like Mr. Naughty.
Last week, the X Factor boss and Britney Spears, were on Jimmy Kimmel's chat show.
Jimmy asked them to play a game wherein they would play a newlywed game. They were asked the same question to find out if they could guess what the other thinks.
When n Britney got asked which part of her body she believed Simon thought was the sexiest about her - she politely said 'my arms'. However, Simon wasn’t thinking about her arms and said 'her t*ts'.
There was another question where Simon was asked what Britney's favourite curse word was, to which he guessed 'c**k', but she said 'p***k', prior to shouting: 'I was close! I got the 'ck' so i should get two points for that.'
Last month, the four judges, were in a press conference via a videolink, where Cowell implied at what viewers can expect from the new additions to the panel.
'Demi is a brat,' he told reporters. 'But there's something likeable about her. Britney's quite mean, as you'll discover.'
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