The MTV Video Music Award for Best Hip Hop was first given out at the 1999 MTV Video Music Awards. The award, according to MTV, was originally intended for hip hop songs that incorporated both R&B and rap elements, separate from rap music videos (which were instead honored by Best Rap Video), citing rap-singing artists such as TLC and Lauryn Hill as examples. This explains the recognition of songs such as "Thong Song" and "I'm Real (Remix)".
The award was not given out in 2007, as the VMAs were revamped and most original categories were eliminated, however, Best Hip Hop Video was reinstated in 2008. By then, though, the rules had relatively changed, as R&B and rap videos also became eligible for nominations in this category since the awards for Best Rap Video and Best R&B Video were not brought back.
Drake owns the most nominations, with a total of fifteen. Nicki Minaj has the most wins in this category, with a total of five moonmen.