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Grammy-winning musician Macy Gray has been in the music industry for over two decades. Throughout that time, the “I Try” singer has crafted her own unique sound and musical identity. But when she was first getting into the music industry, she looked up to women like hit rapper Lil’ Kim.

Macy Gray wearing gray
Macy Gray | Jerod Harris/Getty Images

Lil’ Kim rose to fame in the late ’90s

Lil’ Kim first started rapping in the mid-1990s as a part of Junior M.A.F.I.A., the group formed by her friend (and fling) The Notorious B.I.G. She released her debut album Hard Core in 1996 and rose to fame with hit songs including “Crush on You” and the iconic “Not Tonight” remix with Da Brat, Lisa “Left Eye” Lopes, and Missy Elliott. The album was certified double platinum with over two million copies sold.

Kim continued to tour throughout the late ’90s. In 2000, she released her sexually charged album The Notorious K.I.M., which solidified her status as a sex symbol in hip-hop and a talented rapper who could compete alongside the men in the industry.

Macy Gray wanted to be like Lil’ Kim when she was starting out

Macy Gray worked throughout the ’90s to break into the music industry, watching as women like Lil’ Kim staked their claim in a crowded field. In July 1999, Gray released her debut album On How Life Is. The album’s second single “I Try” became her breakout single. It peaked at No. 5 on the Billboard Hot 100 chart (her highest-charting single to date) and won the Grammy Award for Best Female Pop Vocal Performance, also earning nominations for Record of the Year and Song of the Year.

But despite all the success and popularity the song brought her, Gray herself wasn’t too jazzed with the song at the time. In an April 2022 interview on The Real, she was blunt about how she felt about the track.

“Actually, I fought with my label not to put it out,” she laughed. “I was like, ‘That’s so sappy.’ I wanted to be a rebel, you know? I wanted to be Lil’ Kim, you know?”

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Macy Gray’s career in the past two decades

Gray has continued to work hard ever since the release of “I Try.” She’s released 10 studio albums in total.

Now, Gray is gearing up for the release of her eleventh album, titled The Reset. The album’s title and cover reference Gray’s calls for a “reset” in 2021 to redesign the American flag to be more reflective of the United States today. Later this year, she’ll embark on a European tour with her band, The California Jet Club.

In addition to her music, Gray has also appeared in a number of movies and TV shows over the years, including Training DaySpider-ManScary Movie 3Lackawanna BluesIdlewildFor Colored Girls, and The Paperboy.