Brad "B-Rad G" Gluckman

Brad "B-Rad G" Gluckman is a wealthy, Jewish adult in his early 20's, played by Jamie Kennedy, who believes he is going to be the next Eminem. He talks, dresses, and attempts to rap just like people who live in the "hood". He is the protagonist of the film.

History
Bradley 'B-Rad' Gluckman (Jamie Kennedy) is a young privileged white man from Malibu, with aspirations of being "the biggest rapper that ever was". B-Rad dresses and speaks like a gangster and essentially thinks and acts like he is black.

After Bill's campaign manager Tom Gibbons (Blair Underwood) gets irritated with B-Rad's constant interruptions with the election, Bill decides that B-Rad must see a psychiatrist, Dr. Feldman (Jeffrey Tambor). Dr. Feldman tells B-Rad's parents Bill and Bess (Bo Derek) that B-Rad has the most serious case of "gangstaphrienia" that he has ever seen. Tom then has an idea to hire two actors, PJ (Anthony Anderson) and Sean James (Taye Diggs) to try to scare B-Rad back to normal. Although Bill thinks it could get dangerous, he reluctantly agrees. With the help of PJ's cousin Shondra (Regina Hall), they kidnap B-Rad and take him to the ghetto.

Shondra tries to convince B-Rad that if he stops acting like a gangster, they will let him go. B-Rad tries to tell Shondra he cannot, it is who he is. The actors then try plan B, forcing B-Rad to rob a convenience store owned by a Korean American family. Later, realizing they forgot to call to tell the owner that the robbery was fake, after sending B-Rad in, PJ and Sean begin to worry the plan will fail and they will go to jail. B-Rad finds his emergency stash of cash in his pants and pays for the alcohol he was supposed to steal for the two gangsters. B-Rad then lies to them and says he stole it. When they find a receipt in the back, B-Rad says he stole that, too.

The actors try taking him to a scary movie to get him to stop trying to be a gangster. All B-Rad does is get scared and screams and throws popcorn all over the place, ruining the movie. At this point, PJ and Sean are frustrated and decide to take B-Rad to a club and have him compete in a rap battle. B-Rad ends up getting thrown off the stage for saying the N word in one of his rhymes. He is thrown in a dumpster while the actors laugh at him hysterically. B-Rad feels as if he never could rap, until Shondra changes his mind.

After she cheers him up, they kiss. B-Rad takes it too far and gets on top of Shondra, only to be thrown off the bed by her. She storms out of the room and B-Rad takes a nap. He dreams about a rat by the name of Ronnie Rizzat (voiced by Snoop Dogg) and he tells to just be himself, but the rat "would rather eat garbage than listen to his tired-ass rhymes". His dream ends and B-Rad hears the actors on the phone with Tom. B-Rad then realizes the whole thing was a joke, including Shondra.

Angry, B-Rad storms out of the house. Sean and PJ follow him outside, only to be held hostage by a real gangster Tec (Damien Dante Wayans), who is also Shondra's ex-boyfriend, whom B-Rad encountered at the club. Tec and his crew kidnap B-Rad and the actors and take them to an empty parking lot. Tec calls Tom and tells him if Bill wants to see his son again, they have to give him $500,000. Tom has another plan, if they kill B-Rad, Bill will get more votes for his campaign.

Tom tells Tec there is no deal. Tec points a gun at B-Rad and a pack of other gangsters pull up and start shooting at B-Rad and the others. B-Rad then takes two Uzis, hops on the roof of a car, and starts aiming fire at all of them. Scaring them away, Tec realizes B-Rad is gangster himself. He then makes B-Rad one of them, leaving the actors tied up and brought to a party. While at the party, everyone sees B-Rad on television shooting at the gangsters with a security camera catching everything.

Worried and realizing he needs to be a better father to B-Rad, Bill tells Tom what happened and asks Tom to help him. Tom, though, is more focused on the campaign, but Bill says he would rather lose the election than his son. Tom, now frustrated with Bill, yells at him and says that if anything happens to B-Rad, he can turn it around to make Bill the victim, instead. Bill realizes that Tom is hoping that something bad will happen to B-Rad to get votes and fires Tom before driving to South Central Los Angeles to find his son. B-Rad's crew Hadji (Kal Penn), Mocha (Nick Swardson), and Monster (Keili Lefkovitz) also see the news and grab their best weapons ( a musket, a spear gun, and an RPG) to save him.

Shondra shows up to the party, after seeing the news as well. Shondra sees PJ and Sean and asks where B-Rad is; they tell her, only to be shut up by other gangsters there. Shondra enters a bedroom, where B-Rad and two other woman are taking off his pants. Shondra acts like his baby mama to get them to leave. B-Rad gets mad and shoots his foot, not thinking the gun is real. Realizing it is, he jumps around the room in pain. Shondra tries to help him as Tec walks in, thinking Shondra is hooking up with B-Rad. Tec is furious and threatens to shoot them both.

Bill crashes through the wall and tries to reason with everyone, only to be held at gunpoint. B-Rad's crew members crash through the wall, as well, and point their guns at Tec and his crew. Bill apologizes to B-Rad for not always being there for him and accepts B-Rad for who he is. Accepting his apology, they hug. Tec is still angry, and ruins the moment with his crew and him pointing their guns at B-Rad's crew. B-Rad decides to rap, only annoying Tec.

B-Rad then begins to take the weapons, not wanting any violence. Mocha, agreeing with B-Rad, accidentally fires his gun, which hits Monster in her chest armor, causing her to accidentally shoot B-Rad in the buttocks with her spear gun, resulting in him dropping one of Hadji's rocket launchers, which fires right into the oven. Everyone runs out of the house just before it blows up. B-Rad is treated for his wounds while Shondra talks to him. B-Rad had trouble telling what was real and what was not, so Shondra kisses him to help him. Shondra also ends up opening her own salon, and B-Rad and she get back together. Bill wins the election for governor of California, and is glad to have his son with him.