Responding to accusations of sexism and misogyny, Justin Timberlake issued an extensive, public apology to Britney Spears and Janet Jackson on Friday.

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The singer-actor posted on Instagram, a week after a New York Times documentary on Spears triggered criticism of Timberlake for the way he treated the pop star after their breakup. Timberlake’s apology to Jackson seemed to come from the infamous “wardrobe malfunction” halftime show during Super Bowl XXVIII in Jacksonville, Florida.

“I’ve seen the messages, tags, comments, and concerns and I want to respond,” Timberlake wrote on Instagram. “I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right. I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism.

“I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed.”

Both incidents go back more than two decades.

Timberlake, 40, and Spears, 39, dated when both were teen stars, Variety reported. Timberlake publicly said at the time that he had slept with the pop star and obliquely accused her of cheating on him, the website reported. That accusation was borne out in a music video for Timberlake’s 2002 song, “Cry Me a River,” which featured an actress who resembled Spears, Variety reported.

That situation resurfaced in the Feb. 5 documentary, “Framing Britney Spears,” which premiered on FX and Huli. The documentary focused on the conservatorship Spears has been under since 2008, but also addresses the sexist and judgmental way she has been treated by the media and others during her career, The New York Times reported.

A judge on Thursday ordered Spears’ father to develop an investment plan and budget for the singer, KCBS reported.

The documentary unleashed calls on social media for direct apologies from people who made jokes at Spears’ expense or interviewed her in ways now viewed as insensitive, sexist or unfair, the newspaper reported.

Timberlake is now married to actress Jessica Biel.

Jackson came under fire during the Super Bowl halftime show when Timberlake ripped off Jackson’s bodice to reveal her right breast, CNN reported.

Timberlake later apologized to the Super Bowl audience, as well as “anyone offended,” the Times reported. At the Grammy Awards, which that year followed the Super Bowl, he won two awards while apologizing for the “unintentional” incident. Years later, Timberlake said in an interview with MTV, “There could have been ways that I could have gone about it, handled it better.”

Cox Media Group