During the peak of her career, Britney Spears worked with the Black Eyed Peas’ Will.i.am and created one of her worst songs ever. Somehow, that led to more collaborations between Spears and the rapper that took the “Womanizer” singer‘s career in the wrong direction. While the press has become more sympathetic to Spears, her career never recovered from those Will.i.am collaborations.

Britney Spears and Will.i.am made 1 of the worst songs of the 2010s together

Both during his time with the Black Eyed Peas and his solo career, Will.i.am wrote many vapid, annoying songs. Many of those vapid, annoying songs were very successful. Regardless, as the 2010s wore on, Will. i.am’s sound seemed more and more passe. Sadly, Spears worked with him during this period.

In 2011, the duo made the song “Big Fat Bass” for Spears’ record Femme Fatale. That album boasts four memorable singles — “Hold It Against Me,” “Till the World Ends,” “I Wanna Go,” and “Criminal” — but “Big Fat Bass” isn’t up to that standard. It’s not up to any standard. It’s a maximalist mess that uses a bizarre metaphor where Will. i.am’s … private part … is called a “big fat bass.” This unholy marriage of house music and silly innuendo should have been the last Spears/Will.i.am song, but things only went downhill.

Britney Spears didn’t evolve with the times when she desperately needed to do that

The two artists worked together for a 2013 dance song called “Scream & Shout.” That track performed pretty well, reaching No. 3 on the Billboard Hot 100, but it was an earsore. It’s repetitive and abrasive. While artists like Lorde and Tove Lo were making pop music moodier and darker in 2013, Spears and Will.i.am were behind the times.

Afterward, Will.i.am was tasked with producing Spears’ next album, Britney Jean. The lead single from that record was “Work B****,” an EDM banger that was even less hip. Britney Jean was a car wreck that ended Spears’ time as a hitmaker. Her next album, Glory, didn’t produce any hits. Spears later released a duet with Elton John called “Hold Me Closer,” but the song quickly dropped out of the top 10. Spears’ time as a hitmaker seems to be over and Will.i.am was instrumental in her downfall.

What the Princess of Pop thought of Will.i.am

During a 2011 interview with Rolling Stone, the “…Baby One More Time” star revealed that she had a thing for the Black Eyed Peas. “I love the Peas, but I also love Deadmau5,” she revealed. “I guess I’m all over the place. Lately, I have been listening to Robyn and Adele non-stop, but I also love to find new artists that very few people know about. It’s one of my favorite things to do because it’s like being part of a secret. Friends and people around me are always showing me new artists that they love and that’s how I learned about Sabi and ended up working with her on ‘(Drop Dead) Beautiful.’ I have always wanted to feature a new artist on one of my albums, and she is really cool.”

At the very least, Spears’ collaborations with Will.i.am seemed to come from a place of admiration. “The Peas make incredibly catchy, fun pop/dance records, and I love Will. i.am’s style,” she said. “I have always wanted to do a song with him and would love to work with him more in the future. He is so interesting.”

Spears might have another hit someday — but she is going to have to run away from Will.i.am as fast as she can.