Timberlake said in an Instagram post that he "benefited from a system that condones misogyny and racism" and that he was sorry for all the times his actions had "contributed to the problem."
"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," Timberlake wrote.
Timberlake's message came after Instagram users flooded his account with comments calling for him to apologize to Spears for his behavior following their breakup in 2002, which was highlighted in the documentary Framing Britney Spears. That year, his hit song "Cry Me a River" featured a Spears lookalike and appeared to blame her for cheating on him.
"He essentially weaponizes the video for one of his singles to incriminate her in the demise of their relationship," Wesley Morris, a New York Times critic at large, said in Framing Britney Spears.
Timberlake's song and his comments about their sexual relationship at the time fueled an already toxic tabloid obsession with Spears and stoked the misogynist narrative that she was solely to blame for their much-publicized breakup.
He also came out mostly unscathed after the infamous 2004 Super Bowl incident in which he ripped off Jackson's bodice to expose her breast on live television, while her career and reputation suffered.
Timberlake addressed the deluge of online criticism he has received since the documentary came out, saying, "I've seen the messages, tags, comments, and concerns, and I want to respond."
He added, "I also feel compelled to respond, in part, because everyone involved deserves better and most importantly, because this is a larger conversation that I wholeheartedly want to be a part of and grow from."
Timberlake also said his apology didn't "absolve the past" but that he wanted to take accountability for his missteps.
"I care deeply about the wellbeing of the people I love and have loved," he said. "I can do better and I will do better."