Justin Timberlake has apologised to former girlfriend Britney Spears and singer Janet Jackson.
Timberlake has previously been accused of misogyny by some over the way he treated Spears during their relationship and break up, as well a performance he did with Jackson at the Super Bowl in 2004.
In a post on Instagram, he said he had "seen the messages, tags, comments, and concerns and I want to respond".
Spears' treatment has come under renewed scrutiny following the release of new documentary Framing Britney Spears, which examined her public unravelling in 2007.
The documentary featured a clip of an interview with Timberlake, in which he discussed how he hired an impersonator of her for the music video of Cry Me A River.
Spears and Timberlake had a high-profile relationship in the late 1990s and early 2000s, before splitting in 2002.
Jackson, 54, and Timberlake, 40, performed at the Super Bowl in 2004 together, with the controversial wardrobe malfunction happening during the track Rock Your Body.
As he sang the lyric "I'll have you naked by the end of this song", Timberlake pulled at a part of Jackson's costume, exposing her right breast, which was covered only by a silver decoration.
Timberlake, 40, said in a lengthy social media post: "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 apologise to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed."
He added that he felt "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".
Timberlake said his industry is "flawed", adding: "It sets men, especially white men, up for success. It's designed that way.
"As a man in a privileged position I have to be vocal about this.
"Because of my ignorance, I didn't recognise it for all that it was while it was happening in my own life but I do not want to ever benefit from others being pulled down again."
He said his apology is a "first step and doesn't absolve the past".
"I care deeply about the wellbeing of the people I love and have loved. I can do better and I will do better," he said.