Canadian leader Justin Trudeau said he is “p****d off at himself” after an old photo of him in 'brownface' emerged.
The photo which originally appeared in a 2001 yearbook was republished by Time magazine, and shows the then-29-year-old Trudeau in a turban and robe, with a darkened face and hands.
He was attending an ‘Arabian Nights’ themed dinner at West Point Grey Academy, a Canadian private school where Mr Trudeau had worked for a year before entering politics.
The prime minister said he “should have known better” and is “deeply sorry”.
“I'm going to ask Canadians to forgive me for what I did. I shouldn't have done that. I take responsibility for it. It was a dumb thing to do,” he said.
“I didn’t consider it racist at the time, but now we know better.”
Mr Trudeau was one of several people in ‘Arabian’ dress at the function, however he was the only one photographed with darkened skin.
He revealed it was not the first time he had painted his face; he also appeared as Jamaican-American singer Harry Belafonte during a talent show.
Canada’s Conservative opposition leader Andrew Scheer said 'brownface' was racist then and now.
“What Canadians saw this evening was someone with a complete lack of judgment and integrity and someone who is not fit to govern this country,” he said.
Mr Trudeau launched his re-election campaign only a week ago, ahead of a national vote on October 21.
Local polling before the image emerged showed Mr Trudeau was on track to win a second term.