Justin Timberlake apologized to Britney Spears and Janet Jackson in a new statement posted on his Instagram account. The statement follows the singer’s recent appearance in Framing Britney Spears, a New York Times documentary about Spear’s career and struggle for the conservatory, in which Timberlake’s role in damaging the public image of Spears after their widely publicized breakup in the early 2000s has been described. Spears was humiliated after breaking up with the media, while the film shows a radio clip from that time in which Timberlake bragged about sleeping with her.

“I am very sorry for the times in my life when my actions added to the problem, when I did not speak properly, or when I did not speak up about what was right. I understand that in these and many other moments I came up short and benefited from a system that tolerates misogyny and racism, ”he wrote. “I would like to specifically apologize to Britney Spears and Janet Jackson for caring for and respecting these women and for knowing that I have failed.”

Timberlake was long criticized after the 2004 Super Bowl halftime performance with Jackson, in which Timberlake exposed Jackson’s nipples during the show in a malfunction later known as a cloakroom malfunction. The backlash to the incident resulted in Jackson’s music videos being blacklisted on MTV and her Grammy Awards invitation withdrawn later that year. Timberlake was allowed to attend (and perform) the Grammys after apologizing.

When Timberlake pondered the incident in a 2018 interview with Zane Lowe ahead of another Super Bowl performance, he said he “stumbled upon” what happened to Jackson. “I had my wires crossed and it’s just something to look back at and say, ‘Ok, you know, you can’t change what happened, but you can go forward and learn from it,'” he said at the time. Weeks later, Jackson publicly suppressed rumors that she would be performing alongside Timberlake for the 2018 halftime show.

Later in the statement released today, Timberlake wrote, “I have not been perfect at managing all of this throughout my career. I know this apology is a first step and doesn’t resolve the past. I want to take responsibility for my own failures in all of this and be part of a world that stands up and supports. “