|The Black Rider is a mysterious participant in the 2011 Greendale Community College Paintball tournament. He wears a traditional gunslinger outfit along with a black duster and spurs. Although equipped with two paintball pistols, his weapons of choice are a pair of paintball shotguns that are strapped to his back. He is literally a gun-for-hire and makes it clear he is playing not for the prize but because he is being paid to participate. His first and only appearance was in the Season Two episode "A Fistful of Paintballs". He is portrayed by actor Josh Holloway.|
|In the study group's second year together at Greendale, a mysterious player entered the 2011 Paintball Assassin game. His real name is unknown, but he quickly becomes a notorious opponent to be feared. The other players nickname him "The Black Rider". Jeff, Annie and Abed encounter him after he eliminates Pavel, and they barely manage to escape. After reuniting with the rest of the study group, they arrive at Pierce's headquarters, dubbed "Fort Hawthorne". They then learn more about his identity and reputation. The trio encounter him again while going on an expedition for paintball ammunition. Temporarily splitting off from Jeff and Abed, Annie eliminates the Greendale cheerleaders and ends up in pursuit of Chang.
|She loses him and finds herself in the anthropology classroom alone. The Black Rider sneaks up behind her and gets the drop on her. Flirting with her, he disarms her and offers to make her elimination as painless as possible. Unaware that the gun she had borrowed from Jeff had been filled with blanks by Pierce, he unsuccessfully tries to shoot her with it. Jeff and Abed show up, causing him to take Annie hostage and use her as a shield. After a quick elbow to his ribs, she manages to get free. He retreats, deftly managing to avoid both Abed and Jeff's assault. The Black Rider then heads to the cafeteria and seemingly eliminates everyone at Fort Hawthorne. Annie and the study group arrive sometime later having just acquired new weapons from a hidden stash of weapons in Dean Pelton's office.
|Finding Pierce hiding in the bathroom, Annie confronts him over his treachery. She challenges him to a duel as the study group watches on. The Black Rider reappears which causes an insecure Jeff to challenge him too. Before a shot could be fired, Pierce suddenly collapses claiming he is having a heart attack. Despite being warned by the study group that he is faking, The Black Rider goes to help him only to get shot by Pierce. He calls his employer and lets him know that he was eliminated. He informs Annie and the study group that his job was to ensure that no one from Greendale won the paintball contest's prize money. He also adds that the circumstances surrounding the paintball competition are "much bigger than you can imagine". It is later revealed that he was first step of a master plan conceived of by City College's Dean Spreck to destroy Greendale.
- The Black Rider's last words on the show referring to Annie as "Bean Allergy" mirrors Josh Holloway's character in the TV series, Lost, James "Sawyer" Ford's tendency to give people nicknames.
- Josh Holloway co-starred with Chevy Chase in the 2011 movie Stay Cool. Hillary Duff, who guest-starred in the Community episode "Aerodynamics of Gender" as Meghan also appeared in the film.
- “Who the hell are you?”— Jeff
- “The guy that's going to win.”— The Black Rider
- “I wouldn't go to this toilet with my big sister's toe.”— The Black Rider disses Greendale
- “Look, if you're half the cool cowboy you pretend to be, you'll respect that we've got a situation playing out here and let us be until it's settled.”— Jeff
- “Sure thing. But once it's settled, I'm taking out everybody in this room....starting with you, Mr. Insecure.”— The Black Rider
- “I'm outta here. I got Coldplay tickets." --'The Black Rider”
- “Coldplay?" --'Annie”
- “Too late, bean allergy. You blew it.”— The Black Rider