16. Kimbo Slice
The ultimate streetfighter on this list, the late Kevin Ferguson is a legend. Initially, he had hopes of making it in the NFL but that never happened. So, he actually turned streetfighting into his career, going viral across the internet. He became such an icon that Rolling Stone would call him ‘The King of the Web Brawlers.’

In 2003, he began taking unsanctioned fights that were mostly arranged through adult website SublimeDirectory. In his first taped fight against a man called Big D, Ferguson left a large cut beside his eye, leading to the addition of ‘Slice’ to his childhood nickname ‘Kimbo.’