Dunno if the challenge was for the female Kelly Miller (I) or the male Kelly Miller (IV). I'll solve both...
Kelly Miller I (George of the Jungle) Richard Roundtree (Shaft 2000) SLJ
Kelly Miller IV (New Guy) Tracy Tobin (Super Troopers) Brian Cox (The Bourne Supremacy) Matt Damon (J&SBSB) Hamill/Fisher
Happy Birthday, Dabney Coleman.