Usher and Chilli's Breakup Timeline

September 2024 · 5 minute read

This week marks 18 years since Usher released what I (and anyone with taste) consider to be the best R&B album of all time: Confessions.

Of course, there was more to the pop culture obsession than just Usher's silky smooth voice. When it was released, many fans believed that the themes of infidelity and cheating throughout the record, which was the top-selling album of 2004, were about Usher's own relationship missteps with TLC's Rozonda "Chilli" Thomas.

The songstress has since denied that the album is about her relationship, and songwriter Jermaine Dupri later spoke about the true inspiration for the chart topper. But Chilli and Usher's messy end, which coincided with the release of Confessions, has stuck with me for years.

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The early 2000s were responsible for some of the best (and worst) trends to date, one of which is the super-couple. You could not walk into a grocery store without seeing Brangelina or Bennifer on the cover of tabloid magazines. The R&B world had its own It couple: Usher and Chilli. At the time, she was one-third of the best-selling female music group in the US, and he was one of the best-selling R&B artists of all time. Could it be any more obvious?

The singers met in 1993, when Usher signed to the same label as Chilli, LaFace Records, but didn't start dating until 2001. Soon after, the "No Scrubs" singer made cameos in a few of Usher's music videos, including "U remind me" and "U got it bad." They also attended the Grammys as a couple in 2003, shortly before the they split up amidst rumors of cheating on Usher's part.

In a 2013 interview with Us Weekly, Chilli said that Usher never cheated on her, and that he was her first "real love." But this recollection contradicts some of her previous statements about their breakup.

During a2004 interview with The Bert Show on Atlanta's Q100, Chilli said the "Superstar" singer committed the "ultimate no-no" and that she "will never take him back." She also said that if "someone cheat one time, you don't wait around to see if they're going to do it again."

During a 2010 episode of VH1's "Behind the Music," Chilli said that she "kept hearing about it, then I went to him and I asked him and he … admitted it. You know I just, I felt like … a fool, I felt like everybody knew something and I didn't, and I'm … just now finding out."

While the technicalities could be debated, the general consensus during that time was that she left him in the wake of these, um, confessions.

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To say that I am an Usher fan would be a pretty big understatement. The password to my phone is 8701, the title of his third studio album, and he has been the answer to an embarrassing number of my online security questions in the past. So when the rumors swirled that Chilli left him due to this alleged bad behavior, I was effectively shook.

Breakups are sad — full stop. And I would never rejoice in the romantic shortcomings of others. However, seeing a woman leave such a powerhouse of a man because he allegedly crossed a boundary (even if it only seemed that way to the public) served as an invaluable lesson in dating for me.

There are, unfortunately, too many examples of women sticking around after men cheat or publicly embarrass them in some way. The resulting narrative — that cheating is just a part of the "ups and downs" in relationships — should be thrown out. It's "in sickness and in health." Not in sickness and when he can't keep it in his pants.

Her decision to leave someone who I, at the time, thought was the best thing on two feet, showed me that boundaries and standards should not be compromised, not even for dimples and a diamond record.

I think of Chilli's strength often, especially when my well-meaning friends tell me my standards are too high or not realistic for the current dating climate. It can start to feel like maybe all straight cis dudes cheat, and that's just the price you pay for being attracted to men. I, however, reject that notion, and seeing my sentiments reflected in celebrity couples feels good!

I'm not going to lie and say maintaining these standards is easy. It can be lonely, but in the words of Toni Morrison, "my lonely is my own." It has not been given to me by an aspiring Soundcloud rapper or finance bro, and that, I guess, is my power.

Chilli has reflected fondly on her time with Usher, and they have both since said that if they had met later on in life, things might have been different. But alas, they met when they did, and Chilli has influenced my perspective on relationships for almost twenty years later: faithfulness is not too much to ask for, and if it is, then I'd rather be single.

Breakups That Broke Us is a biweekly column about the failed celebrity relationships that convinced us love is dead.

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