Ryan Ridley is a man whose life was saved by Jeff Winger and found himself practically becoming an indentured servant to his Samaritan. He was asked to perform a variety of tasks which he dutifully did for three years. No matter how demeaning the job was he did this without complaint hoping one day his debt would eventually be settled. His first appearance was in the Season Six episode "Grifting 101". He is played by real life "Community" writer Ryan Ridley.
In the 2015 Spring semester at Greendale, Ryan Ridley was asked by Jeff to help con his fellow faculty member Professor DeSalvo who taught a Grifting class. Ryan was tasked to play the part of a telegram messenger and borrowed his costume from Dean Pelton's collection of outfits. He interrupted DeSalvo's class to deliver a fake telegram to Elroy Patashnik which informed him that he just inherited a fortune form his dead grandmother who just passed away. When DeSalvo saw through the ruse, Jeff had Ridley take part in another con which took place in the Teachers' lounge.
Telegram for Elroy Patashnik!
He was asked to leave a lottery ticket behind on a table as bait for DeSalvo. However, the Grifting professor saw through the scam having recognized Ryan as the telegram messenger. Sometime afterwards, Ryan went to Jeff's office to check in with him and told him he returned the costume he used to Dean Pelton. Ryan then asked if there was anything else he was needed for and was visibly disappointed when Jeff asked him for another favor. He replied he could use his help on the weekend as he needed his assistance to flip the mattress on his bed. Ryan reluctantly agreed and as he walked away recalled how his relationship with Jeff Winger started.
Jeff saves Ryan's life.
Three years ago he was working out in a gym when he lost control of a barbell he was pressing which landed on his throat and was choking him. Jeff was also at the gym and helped him remove the weight saving his life. Since then Jeff has been using the incident to get Ryan to carry out various odd jobs for him. This included pouring him drinks, washing his Lexus, shining his shoes, dropping off his dry cleaning, dusting his office, picking up some coffee for him, watering his plants, stealing office documents, and giving him massages. Until his debt is settled to Jeff's satisfaction, Ryan reluctantly is at Jeff's beck and call ("Grifting 101").