8. Jazz
Jazz was one of the legitimately toughest Divas of her era, making a name for herself by beating the likes of Trish Stratus, Lita and others during her time. Seeminlgy to prove a point, Women's Champion Jazz challenged Bubba Ray Dudley to a match for the Hardcore Championship. Women had won the Hardcore title before, but hadn't competed in a one-on-one anything goes match with a man before. Although the majority of the match was mostly comedic, it was contested under hardcore rules, and Jazz didn't shy away from the use of weapons, and Bubba wasn't shy about performing with a woman. So the match was actually a ruse, as Jazz was just a distraction so that Steven Richards could take advantage of the 24/7 rule and pin Bubba for the title; but at least Jazz can say she competed in a singles hardcore match with a man.