Cybil Bennett is first introduced when we see her riding on her motorcycle, quickly passing Harry and his daughter in the opening sequence of Silent Hill. Shortly before Harry crashes his jeep, Cybil's motorcycle is seen lying off to the side of the road.
After Harry is first attacked by one of the Silent Hill demons, Cybil enters the café and meets Harry for the first time. She is from the neighboring town of and was sent to investigate the strange goings on in Silent Hill. She likes Harry and agrees to help him find his daughter. She leaves to investigate the town some more and leaves Harry with a gun and tells him to be sure not to shoot her with it, which lends itself to a bit of foreshadowing to what will happen later in the game.
When Harry enters the Antique shop, Cybil appears once more. She reveals that there was much drug trafficking in Silent Hill. Cybil believes that is what is responsible for all the weird things that are happening. Harry talks of the occult and demons, but Cybil believes it has to do with the drug trade.
Cybil’s third appearance is in the boat by the resort. Harry again tells her that everything that is happening has to do with the supernatural. Cybil still does not believe. They agree to split up and look for Harry’s daughter, Cheryl. Cybil says she will search the Amusement Park, while Harry goes to the lighthouse.
A cutscene shows Cybil being stalked and attacked by something. When Harry meets her again on the merry-go-round in the amusement park, Cybil has been infected by the same parasite that possessed the doctors and nurses in. Cybil immediately draws her gun and attacks Harry. Harry can save her if he possesses the Red Liquid found in the doctor’s office in the Alchemilla Hospital. If he does not Harry must kill Cybil and her story ends.
If Cybil is saved, her last appearance is at the final boss battle at the end of the game. She tries to help Harry confront Dahlia and Alessa Gillespie but is knocked away by Alessa’s telekinetic powers.
The Bad ending shows Cybil regaining consciousness, slapping Harry out of his shock and getting him to run while the “ Otherworld” destroys itself. The Good ending shows Cybil following Harry through a portal which Alessa created. In this ending Harry has a baby given to him by Alessa. After the credits we see Cybil and Harry together in the cemetery finding the baby. Cybil has now replaced Harry’s wife in this video.
In Shattered Memories, Bennett plays a more significant role than the first Silent Hill. The player's actions during the course of the game will have a lasting effect on Cybil in terms of her appearance and personality.