The field is wide: Tiny Lister as Deebo, John Witherspoon, Bernie Mac, Faison Love (as transcribed), Paula J. Park (as transcribed) as Joy, Regina King, Stanley, little Chris and Smokey's mom, who is only in a couple of scenes asking Smokey to buy cigarettes and talking on the phone; Craig and Smokey are excluded as principals.
One host would have said Joy for her iconic scene but after rewatching lands on John Witherspoon for the gun speech, that a gun does not make you a man and you fist fight, win or lose, and stay alive, which plays a little after-school but he goes for it; a John Witherspoon impression by Charity is teased.
Red is argued for as the most thankless role, getting beaten up and clowned the whole movie, played well, with the touching scene of him sobbing at his car and pulling off.
Witherspoon and DJ Pooh's Red are called great, but Deebo gets it: he has his own music, his name persists as a word for a bully, and he is so iconic that Tiny Lister throwing the detonator off the ship in The Dark Knight reads as Deebo moved to Gotham, arrested and folded into the Joker's plot.
The script was written with DJ Poo (as transcribed) as Smokey, but New Line would not sign off because he was not a big enough star, which one host calls a smart move; Chris Tucker, not yet established but on the rise, auditioned for Cube and the rest is history.
Pooh as Smokey would not have worked, but he killed it as Red, a lovely part, especially the way he jangles back to the car after asking about his beach cruiser.
Tommy Davidson and Chris Rock were also considered for Smokey; Rock is rejected as too New York, more famous than Tucker in 1995 but not computing in the role, and his doing Tucker's physical comedy would look like overacting, Tucker reading as a younger, more exuberant spirit where Rock can be hardened.
Tommy Davidson was also supposed to play the crackhead Ezal; Angela Means, who plays Felicia, has said her agents wanted her to pass because she was so pretty and should have played the pretty girl, which one host finds fair.
A hypothetical recast: Viola Davis as Mrs. Jones, the comedic but strict mother Anna Maria Horsford plays; Davis rarely gets comedic, motherly roles and is pushed into intense crying parts, so the hosts wonder what the role would have looked like with her in 1995 or in a reboot, though whether she was old enough twenty years ago is questioned.