24. Richard Roundtree
Notable Roles: Se7en (1995); Shaft (1971); Brick (2005); Inchon (1981)
Donning doubled-vented suits, leather, and turtlenecks, Richard Roundtree made a name for myself in the seminal role as Shaft, instantly emerging as a cultural icon. His effortless cool and form fitted looks demand attention as he helped pave a way for a new genre in film and showed men that you can look good while serving justice.