How Madonna and Four Female Artists Made Billboard History 36 Years Ago

On May 26, 1990, the music industry finally broke a longstanding trend that had been untouched since the Billboard Hot 100 was introduced in 1958. 36 years ago, for the first time, the chart's top five spots were all occupied by female artists.

The record was achieved by Madonna with her hit single, "Vogue", which shot to No. 1 and joined Heart, Sinead O'Connor, Wilson Phillips, and Janet Jackson in the Top 5. This was a massive accomplishment that had never been achieved before, marking an enormous step forward for female representation in the industry.

Today, it's not that surprising to see female artists at the top of the charts. In an era when pop stars like Taylor Swift and Sabrina Carpenter are dominating streaming, and young talents like Billie Eilish and Olivia Rodrigo are defining an entire generation, the barrier between male and female artists has clearly broken down.

This wasn't always the case, however. While there's always been a place for incredible female musicians on the charts, it was typically male artists or male groups who took up those top spots. Whether it's Michael Jackson or The Beatles, the Billboard Hot 100 was generally dominated by men.

It's very fitting that Madonna was the one to finally break this trend, as she pioneered a whole new generation of female pop artists who blended musical creativity with general appeal to forge a legacy of commercial success. There are very few pop stars today who wouldn't credit much of their inspiration to Madonna.

Janet Jackson's spot in the lineup is also a fun coincidence, as it was her brother, Michael Jackson, who set countless chart records throughout his career. Not only did he score the highest-selling album of all time with Thriller, but he also had the most No. 1 hits on the Hot 100 of any musical artist ever.

Sinead 'Connor, Wilson Phillips, and Heart were all rising stars when they broke into the Top 5 in 1990, but their place among this historic lineup is no less deserved. All three artists went on to have long, successful careers that paved the way for many different genres of female-led music to thrive in the decades that followed.

This story was originally published by Men's Journal on May 26, 2026, where it first appeared in the News section. Add Men's Journal as a Preferred Source by clicking here.

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This story was originally published May 26, 2026 at 9:10 AM.