Richard Wilkins has opened up about the toughest interview of his career.

The Nine Entertainment reporter revealed that a 2015 interview he did with Material Girl singer Madonna, kept him on his toes.

"I guess Madonna would have to be up there. I've done a few interviews with her. She treats it like a sport," Wilkins revealed.

In the interview, Wilkins played a drinking game with the singer, where she told him that their chat would not be "your average interview".

"One of the last interviews I did with her she had a bottle of tequila and two shot glasses. She said if you ask a really good question, I'll have a shot and if you ask a really stupid question you have to have a shot."

As the interview went on the two shot glasses remained empty.

At one point, the singer let out an expletive in response to one of Wilkins’ questions and immediately apologised, to which Wilkins jokingly asked whether she should have a shot for swearing.

"No, that's not part of the... I make up the rules to this game, OK," she quipped, with a smile creeping across her lips.

The two were super competitive as the bottle of tequila remained untouched throughout the interview.

When they discussed Madonna’s thirteenth album Rebel Heart, Wilkins finally broke the streak after asking her a question about changing her image.

Without uttering a word Madonna pours him a shot, to which Wilkins groans, “Oh come on”.

“I always answer the same way,” the singer justified and then told Wilkins to “drink up”.

Wilkins recalled this moment as if it happened yesterday.

"I said, this new record, you know you're going in a different direction... 'Oh, the reinvention question, alright here you go'," he recalled, miming pouring a drink.

"It was all fun and games, but you've got to be on your toes when you interview Madonna, because she does not take any prisoners,” he added.

Image: 9Honey