Entertainment Music Justin Timberlake Apologizes to Britney Spears and Janet Jackson for His 'Ignorance': 'I Have Failed' "As a man in a privileged position, I have to be vocal about this," Justin Timberlake wrote in a lengthy apology on Instagram Friday By Jen Juneau Jen Juneau Twitter Jen Juneau is a digital news writer for PEOPLE since 2016. People Editorial Guidelines Published on February 12, 2021 12:51 PM Share Tweet Pin Email Justin Timberlake is issuing an apology after benefiting from a system he says "sets men, especially white men, up for success" — specifically addressing Britney Spears and Janet Jackson for his past behavior toward them. In a lengthy Instagram post on Wednesday, the singer and actor, 40, began by saying, "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." "I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism," Timberlake continued. "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 added. Timberlake's post comes after the release of Framing Britney Spears, the unauthorized New York Times documentary that included, in part, a section exploring his former romantic relationship with Spears, 39. It included his hit "Cry Me a River" song and music video that seemed to reference their breakup with a lookalike actress and a message that, to many, seemed to blame Spears and depict a revenge fantasy on Timberlake's part. Never miss a story — sign up for PEOPLE's free daily newsletter to stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories. Justin Timberlake's Instagram post. Britney Spears and Justin Timberlake in 2002. Ron Galella/Getty Why Craig Ferguson Refused to Tell "Britney Spears Jokes" During Her Mental Health Crisis in 2007 The documentary also featured a clip of a 2002 interview with Star and Buc Wild that features Timberlake admitting he and Spears had had sex — and the private nature of the revelation upset many fans of the "Toxic" singer. Jackson, meanwhile, was at the center of controversy after her 2004 Super Bowl set with Timberlake, during which she suffered a now-infamous wardrobe malfunction with seemingly no similar repercussions for Timberlake. Controversy ensued, Timberlake and Jackson issued apologies, and the Federal Communications Commission charged CBS — the network that broadcast the game that year — with a $550,000 indecency fine for the incident, dubbed "Nipplegate." Justin Timberlake and Janet Jackson in 2004. Kevin Mazure/WireImage During a 2006 interview with Oprah Winfrey, Jackson stated that she felt "all the emphasis was put on me, not" following the controversy "as opposed to us." Asked if she felt like Timberlake had "left her hanging," the singer replied, "to a certain degree, yeah." Ahead of his own Super Bowl halftime show performance in 2018, Timberlake told Zane Lowe that he had "absolutely" made amends with Jackson, adding: "I don't know that a lot of people know that. I don't think it's my job to do that because you value the relationships that you do have with people." "The industry is flawed," Timberlake continued in his Friday Instagram post. "It sets men, especially white men, up for success. It's designed this way. As a man in a privileged position, I have to be vocal about this." RELATED VIDEO: Janet Jackson's Family Hasn't Forgiven Justin Timberlake for Infamous Super Bowl Performance He added, "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." In conclusion, the former *NSYNC member acknowledged that he has "not been perfect in navigating all of this throughout my career," saying he knows "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," Timberlake said. "I care deeply about the well-being of the people I love and have loved." "I can do better and I will do better," he concluded.