Most Headies won
Who
Modenine
What
9 total number
Where
Nigeria ()
When

The Headies (formerly the Hip Hop World Awards), were inaugurated by Hip Hop World Magazine in 2006 to honour outstanding achievement in Nigerian music. British-born rapper Modenine (aka Babatunde Olusegun Adewale, Nigeria) has, appropriately enough, won nine Headies: Best Rap Album (Malcolm IX – The Lost Sessions, 2006), Best Rap Single ("Cry", 2007) and seven "Lyricist on the Roll" awards (2006–11 and 2013).