Canadian Prime Minister Justin Trudeau is apologizing again for wearing blackface during three separate instances and admits he does not know how many times he’s put on the racist makeup.

"What I did hurt them, hurt people who shouldn't have to face intolerance and discrimination because of their identity. This is something I deeply, deeply regret," he said during a press conference Thursday (September 19), adding that darkening your face “is always unacceptable because of the racist history of blackface. I should have understood that then, and I never should have done it."

Trudeau also says his white privilege blinded him to the racist history involved with blackface. "The fact is I didn't understand how hurtful this is to people who live with discrimination every day.”

Trudeau initially apologized on Wednesday after Time Magazine posted a photo of him wearing brownface at an “Arabian Nights” party in 2001. He also admitted he wore blackface in high school in the late ‘90s while performing “Banana Boat Song (Day-O),” a traditional Jamaican song, which Harry Belafonte recorded and released in 1956.

The Canadian Broadcasting Corp published a photo from that performance that a spokeswoman confirmed as authentic, Reuters reports. 

The third known time Trudeau wore blackface was revealed via video from a Conservative Party of Canada source that was sometime around 1993 or 1994.

Justin Trudeau is running for reelection as Canada’s prime minister. The blackface images are surfacing just a month before the country’s election, which is on October 21.