20. Lil' Kim
People might think it's Nicki's fault that Lil' Kim is on this list, but her downfall started way before Ms. Minaj ever put a wig or even a British accent on. Coming onto the scene in the mid-90s, Kim was a bitch of the finest pedigree: sex, smarts and Biggie's rhymes (literally). She went platinum, won Grammys, and had a course taught about her at Syracuse University.
But then she went to prison in 2005; Atlantic pushed her album out while she was behind bars, and it flopped. Dancing with the Stars, reality shows and her label dropping her: none of it helped. And that was before she started pulling Nicki's weave out of jealousy, before she made people pay for a mixtape that never arrived, and before her plastic surgery became a go-to joke for lazy comedians. That being said, Nicki's heavy-handed swagger-jack certainly didn't help.