The 40-year-old singer and actor apologized to Spears, a singer and Timberlake's ex-girlfriend, and Jackson, a singer who performed with Timberlake at Super Bowl XXXVIII in 2004, in an Instagram post Friday.
Timberlake faced renewed criticism this week following the release of Framing Britney Spears, a new documentary that explores Spears' conservatorship battle and the public scrutiny she's endured during her career.
"I've seen the messages, tags, comments and concerns and I want to respond. 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," Timberlake wrote Friday. "I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism."
Timberlake and Spears started dating in 1999 and had a much-publicized split in 2002. Timberlake appeared to accuse Spears of cheating by featuring a Spears lookalike in his "Cry Me a River" music video.
During Timberlake's Super Bowl performance with Jackson, Timberlake pulled back part of Jackson's outfit and exposed her breast. Jackson bore the brunt of criticism for the incident.
"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 said in his post.
"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 part of and grow from," he added.
Timberlake said the industry is flawed and sets up men, particularly white men, for success. He said he's come to realize that as a man in a privileged position, he has an obligation to speak out.
"I have not been perfect in navigating all of this throughout my career," the star said. "I know this apology is a first step and doesn't absolve the past. I want to take accountability for my own missteps in all of this as well as be a part of a world that uplifts and supports."
"I care deeply about the wellbeing of the people I love and have loved. I can do better and I will do better," he concluded his post.
Timberlake released his fifth studio album, Man of the Woods, in 2018. He most recently starred in the film Palmer, released on Apple TV+ in January.