Hmmmm...... let's see....
Definitely Anthony Andersen for Bookman
Dave Chapelle as JJ
Sanaa Lathan or Vanessa L. Williams (Soul Food) or Malinda Williams as Thelma or the original actress
Kyla Pratt as Penny
Khalil Kain as Michael (I just like Khalil) or Larenz Tate as Michael
Angela Bassett as Florida
John Amos as James (
)
Theresa Randle as Wilona
and Leon can be "My name is Lennnae, do you have a Pennnae..."
That's all I can think of right now