Okay here's my list:
Mr. Gaines - Charles S. Dutton
Col. Taylor - Denzel Washington
Whitley - Essence Atkins but I like Stacey Dash too
Dwayne - Taye Diggs... just cause I wouldn't mind watching a few episodes with him in it
Ron - Dave Chappelle... just cause his show is funny as heck
Kim - Spirit
Freedie - I agree with Rachel True (Mona)
ETA: Jaleesa - Vanessa Bell Calloway
Edited Again to Change Col. Sander to Col. Taylor. I just got shamed so I had to go change it.