**** Exclusive **** Lil' Kim on the set of Ray-J's new video 'Wait A Minute' featuring Lil' Kim, his new single on Atlantic Records, in Los Angeles, Ca. 1/31/01.

Whether she is in the studio, on stage, or casually walking down the streets of New York, Lil’ Kim is going to wear something that is going to make you turn your head. Lil’ Kim (born Kimberly Denise Jones), is a Grammy-winning rapper. She’s also an artist to watch for her daring outfits.

Lil’ Kim began rapping in 1994 when Notorious B.I.G discovered her. The iconic rapper requested that she join his group Junior M.A.F.I.A. The group consisted of Lil’ Cease, Trife, Larceny, Nino Brown, Chico Del Vec, MC Klepto/Kleptomaniac, Capone, and Bugsy. They were all mentored by The Notorious B.I.G. The group was mostly known for their hits “Player’s Anthem” and “Get Money” each making it in the top 20 on the Billboard Hot 100. They released their debut album, Conspiracy, in 1995. The group helped launch Lil Kim’s solo career.

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Lil’ Kim launched her solo career with her debut album Hard Core in 1996. The album debuted at No. 11 on the US Billboard 200 and at No. 3 on Billboard’s Top R&B Albums. Hard Core was the highest debut by a female rapper at the time. The album spawned popular singles such as “No Time,” “Big Momma Thang,” featuring Jay-Z and Lil Cease, and “Not Tonight” featuring Jermaine Dupri. Dupri was also a producer on the album. The remix of “Not Tonight” featured Dupri, Missy Elliott, Da Brat, Left Eye, and Angie Martinez. The single was nominated for Best Rap Performance By A Duo Or Group at the 40th Annual Grammy Awards.

Hard Core was followed by The Notorious K.I.M., which was released in 2000, and La Bella Mafia in 2003. The rapper gained her only Grammy award to date from the 2001 No. 1 hit “Lady Marmalade.” The track featured Mýa, Pink, and Christina Aguilera as well. The song was a remake of LaBelle’s 1974 single of the same name. The song won Best Pop Collaboration With Vocals at the 44th Annual Grammy Awards.

All while Lil’ Kim was heating up the charts with other singles such as “The Jump Off” and “Magic Stick,” she embraced her feminity in a way that had not been seen before in rap.

Take a look at 10 of her iconic looks ranked:

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