Justin Timberlake apologized to Janet Jackson and Britney Spears, acknowledging he "failed" both women in the past.
Fans took to social media to slam Justin for using Britney and Janet to reach the top.
The "SexyBack" singer faced backlash following the recent premiere of Hulu documentary "Framing Britney Spears."
The documentary chronicled Britney's rise to pop superstardom, her spectacular 2008 meltdown, and her ongoing conservatorship battle with her father.
The film briefly explored how Justin capitalized on his 2002 break-up with Britney by boasting about taking the pop superstar's virginity and suggesting she cheated on him with his hit song "Cry Me A River", which featured a Britney lookalike in the music video.
Two years later, Justin hit headlines again for his role in Janet Jackson's Super Bowl Halftime Show debacle, as he ripped off part of her corset and exposed her breast.
Despite reports that Justin and Janet practiced the planned "wardrobe malfunction” in the days leading up to the halftime show, Timberlake distanced himself from Janet -- leaving her to take all the heat, which harmed her career.
Now, the father-of-two has claims he has seen the error of his ways and he spoke out about his white male privilege in a candid Instagram post on Friday.
In the post, he writes, "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."
"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 adds, before blaming the culture of the entertainment industry for enabling such behavior.
"The industry is flawed. It sets men, especially white men, up for success. It's designed this way," Timberlake continues.
"As a man in a privileged position I have to be vocal about this. Because of my ignorance, I didn't recognize 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 concludes: "I have not been perfect in navigating all of this throughout my career. 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 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."
Britney and Janet have yet to respond to the apology.