10. "Not Tonight (Ladies Night Remix)"

The Jermaine Dupri-produced remix "Ladies Night" with Lil’ Kim, Da Brat, Left Eye, Missy, and Angie Martinez is one of the few posse cuts featuring an all-female cast. The Grammy-nominated track would become a top 40 hit.

9. Dancing With The Stars

In the 2009 season, Lil’ Kim made it to the top five of the notoriously difficult dance competition. She left a fan favorite and showcased to the world she is not only a rap superstar but an undeniable all-around entertainer. 

8. Mobb Deep's "Quiet Storm" (Remix)

Released on both the In Too Deep soundtrack and Mobb Deep’s fourth album Murda Muzik, Lil Kim’s verse on the remix is considered one of her best guest appearances. Opening with a famous MC Lyte tribute, (“hot damn ho, here we go again,”) she brings her signature vicious attack style, dominating the track.

7. MAC VIVA Glam Campaign

In 1998, Lil’ Kim, along with Mary J. Blige, became a spokesperson for Mac Cosmetics' VIVA Glam line. Their endorsement led to $4 million in earnings and was the most successful VIVA Glam campaign to date.

6. The Naked Truth

Kim’s fourth album, The Naked Truth, dropped in September 2005 while she was serving a one-year prison sentence. It was released to critical acclaim and she became the first female emcee to receive the coveted 5 Mic Rating from The Source.

5. "All About the Benjamins"

"All About The Benjamins" is one of Bad Boy’s greatest anthems and the label’s first lady delivers the best verse. She’s unapologetically cutthroat versus her laid-back male collaborators focused on big money talk.

4. "Lady Marmalade"

One of the biggest songs of all time, "Lady Marmalade" with Kim, Mya, Pink, and Christina Aguilera topped the Billboard charts, won a Grammy for Best Pop Collaboration with Vocals, and took home Video of the Year at the 2002 VMA awards. It was her first number 1 hot 100 hit and she was the second female rapper in history with a number 1 song on the Billboard Hot 100.

3. 1999 MTV Video Music Awards

Styled by Misa Hylton, Kim wore an asymmetrical lavender jumpsuit with one breast exposed, covered only by a shell-shaped pastie. When she stepped onto the red carpet, it was one of the most memorable moments of the night, until Diana Ross gave Kim’s breast a gentle jiggle when they presented the award for Best Hip Hop Video.

2. "Crush on You" Music Video

A colorful explosion inspired by The Wiz, the Crush on You music video cemented Lil’ Kim as one of hip-hop’s most influential entertainers. Her tough bravado blended with a feminine touch created a style the rap starlets of the next 25 years continued to emulate over and over again. 

1. HARD CORE Album and Artwork

After standout appearances on Junior M.A.F.I.A.’s Player’s Anthem, I Need You Tonight, and Get Money, Lil’ Kim released her debut album Hardcore in the winter of 1996. Charting at number 11 on the Billboard 200 it was the highest debut for a female emcee at the time. It was certified platinum less than a year later. On the album cover, Kim is confident, empowered, and sexy, as she couches down facing the camera with her legs open. Her music made her an unforgettable emcee but her audacity made her an icon.