On November 25, 2002, Justin Timberlake premiered the video for a song (you may have heard it) named ‘Cry Me A River’ from his debut solo album, Justified. There was a time when he was silent about where the inspiration for that song came from. No doubt it was about a prior relationship that crumbled to the ground, but Timberlake stated it wasn’t specifically about anyone in October of 2002. Cut to the premiere of that video directed by Francis Lawrence, and the resemblance of the faceless blonde woman shared a resemblance to Timberlake’s then ex-girlfriend Britney Spears. Again, Timberlake would deny this was a physical metaphor for Spears herself and even went out of his way to call Spears in 2003 to say that much. However, in 2011, Timbaland would confirm the song was about her in his E! True Hollywood Story.

As for what ultimately caused the breakup between Timberlake and Spears, it’s not our business to know. I’m sure we’ve all written letters and long texts that we’ve deleted and talked with friends about how hard a breakup is. However, a clear pattern was established concerning Justin and Britney’s relationship, where one person was provided grace for their expression while the other was not. When Spears released the remorseful piano ballad “Everytime” off her fourth album, In The Zone, in 2004, there would later be Timberlake’s “What Goes Around…/…Comes Around (Interlude)” in 2006 at a time when Spears hit bottom concerning her mental health. Again, Timberlake insisted this song was written from the perspective of a friend who went through a situation of betrayal. But there’s no doubt a certain creative synergy happened between these two artists over many years.

With the release of Spears’ autobiographical book, The Woman In Me, and the specific revelations about their relationship, a discussion of this story has arisen again. Some of it has stemmed from Timberlake’s history concerning the Superbowl incident with Janet Jackson and some of his history of skating criticism. It felt like some healing had happened since. Timberlake had recently released his new single, ‘Selfish,’ off his upcoming album, and Spears praised it. She even apologized for some of the things noted in her memoir, and in 2021, Timberlake specifically apologized to Spears and Jackson. It seemed like all was finally well…welp, until Timberlake’s recent concert in New York at Irving Plaza on Wednesday. In the most Conor McGregor-like aura, right before he performed ‘Cry Me A River,’ he said, “I’d like to take this opportunity to apologize… to absolutely f—ing nobody.” I don’t quite understand why there is an urge to keep this going — especially when the other person involved is looking to move on.

Sure, some circumstances have happened to us that will carry a certain amount of sting. But with that particular comment, Timberlake has propelled people back to 2002 and not talking about his Saturday Night Live set, the new single, his first album in six years, Everything I Thought It Was, or any of the snippets of other songs he played during that birthday show. We’re back to discussing “Cry Me A River,” a song alone on its merit will always be a part of him because it was a hit. But you can perform it in a way that doesn’t knowingly point to all the other things associated with the single. Much like how furious tabloids were to get negative stories, we live in a time and age where negative headlines get engagement. We do have to acknowledge that they were young adults in the public eye at the height of their relationship. Timberlake and Spears should be allowed to grow from the things they went through within the confines of their shared history.

So, why play into the negativity? Playing the bad guy does not serve the art, and portraying a sense of decency while flippant comments like that are made doesn’t help either. Things are flowing against this album as it is. 2018’s Man of The Woods wasn’t received either, and fans will always have the Britney and Janet factors in their heads when they hear his name. Timberlake could have put much of that behind him with this new musical chapter. He elected to keep the fires burning with one remark at a concert before that particular song.