If Jimmy has 100% respect with a clique, male members of that clique may offer to help Jimmy in exchange for $1 if he greets them.
Upon being hired, the other student appears as a blue sphere on the mini-map, and his name and a health meter appears in the upper righthand corner of the screen. He will follow Jimmy around and help him in fights. If the person hired has a projectile weapon, he will instead circle around Jimmy's enemy with his weapon in his hand without attacking him.
If Jimmy attacks the person he hired or attacks members of the bodyguard's clique, the person will stop helping him. He can also cause the person he hired to get bored and wander away if he hides. If he gets far enough away from the other person, either by running or by taking a vehicle, the person will quit helping him. If he takes someone he hired to a place where students from a rival clique will attack him, e.g. a Bully to the Library or a Greaser to Harrington House, those students of the rival clique will attack Jimmy as well, regardless of his personal faction with the offending clique.
After the events of Chapter 1, Russell is always available to be hired. In the mornings he is in the lot in front of the Boys' Dorm, in the afternoons in the school parking lot, and at night in front of the school gates. Once he notices Jimmy, he will automatically offer himself to be hired, even if Jimmy doesn't greet him first.
The chance for a student to offer to help Jimmy seems to be random, and to vary between students. There also seems to be some variance between copies of the games - some players have reported certain characters regularly offering to be hired and others have denied that.
- The six bisexual male characters (Cornelius, Trent, Gord, Vance, Kirby, and Duncan) will only let Jimmy hire them if he hasn't passed any Art classes. If the player passed Art 1 or higher, they will flirt with Jimmy rather than letting him hire them. This is how Duncan's name was discovered.
- Non-Clique Students can't be hired.