Jason

"Well, sweetheart, I'm just getting enough food to keep my strength up so I can make it to the mountains one last time before I put a bullet in my goddamned head.
 * —Jason's response to a store clerk's inquiry about his business in town"

Jason is a former soldier introduced in Among the Damned. Suffering from survivor's guilt, Jason had decided to end his life. While en route to the place he intended to carry the act out at, he runs his car off of the road to avoid hitting a figure that had darted in front of him.

Background
Jason was enlisted in the military with his best friend, Aaron, and it was during a mission that the unit the two served in fell under attack. Jason was the only one to walk away from the incident. He was questioned before a military tribunal for any possible involvement with the attack but no further action was taken, as Jason had been cleared of any suspicion.

Since that event, Jason has suffered from a recurring nightmare. The episodes start off with him standing atop a mountain ridge with a pistol in his hand, ready to kill himself. This vision never lasts long before it transitions to the memory of the attack on Jason's unit. Rather than human combatants in his dreams, it's monsters that beset his unit.

It is this dream that compels Jason to finally attempt suicide and head out to that mountain ridge in his dream. That ridge, however, lies near Silent Hill, and Jason finds himself swerving off of the road in an attempt to not hit a figure that ran out in front of his car as he passed near the town.

Among the Damned
Entering Silent Hill on foot shortly after having crashed his car, the first thing Jason notices is that the town appears unmaintained. Entering a police station, Jason tries to use the phones inside, but the lines are dead. He has no time to contemplate this, as three monsters move away from the body of a police officer and move towards him. Even though he was planning to kill himself, Jason doesn't plan on dying like this, so he jumps over a reception desk and to a gun rack, loaded with shotguns and shells. Taking one down, he has to hit one monster with the stock before he has a chance to load the weapon.

As he's loading his weapon, a young woman (who looks very similar to the figure that ran in front of his car) enters the police station, making herself a new target for the creatures. Before they can attack, however, Jason unloads a shot into each of their heads. Seeing the woman is no longer in the station, Jason heads out into the streets of Silent Hill. As he walks, Jason realizes that he recognizes the woman, a singer named Dahlia. Continuing his walk, Jason comes upon an amusement park where the horses on the merry-go-round have come to life and a woman gets his attention.

Following the woman's voice to the Borley Haunted Mansion, Jason finds Dahlia standing mesmerized in front of a group of monsters. Jason tries to caution Dahlia about the monsters, but she pays him no mind, until she is run through the stomach by a creature with sword legs. Jason grabs Dahlia and pulls her to safety as he fires at the creatures. Running from the amusement park and into the streets of Silent Hill, the pair takes refuge in a maintenance cage, giving Jason a chance to inspect Dahlia's wound. However, she waves his help off. Not long after, monsters begin to descend on the pair. As Jason begins to fire off rounds, a hand grenade dispatches of a majority of the creatures. Aaron, Jason's dead platoon mate, orders the two to run.

Leaving the fight behind, Jason and Dahlia are able to reach a place called Sanctuary, a safehouse that repels the creatures of Silent Hill. Inside, the pair are introduced to the other survivors of Silent Hill and are welcomed to make themselves at home. Dahlia, however, seems to collapses from her wound. After getting her to an infirmary, Jason returns a short time later and finds Dahlia, seemingly healed, up and on her feet. He insists she should be resting since she's hurt, but the woman plays it off, saying her coat got most of the attack. She is then able to seduce Jason.

Waking the next morning, Dahlia asks Jason about Aaron, the man who had saved them the night before. It takes some coaxing, but Dahlia is able to get Jason to reveal his past with Aaron and the attack on his military unit. Jason then decides he can no longer stay in Silent Hill, and the pair make an attempt to leave.

Leaving the safety of Sanctuary, the monsters of the town aren't roaming the streets, having sought shelter of their own from the daylight. Able to walk the town unhindered, Jason and Dahlia don't make it too far into town before an entirely different kind of monster makes itself known to the pair. Stepping out from the fog that covers the town, the entirety of Jason’s undead platoon has hunted the pair down. Aaron, the apparent leader of the group, tells Jason they have business to discuss. Jason, however, has no intention of going near his former unit and begins firing at them with a pistol he procured from Sanctuary.

Aaron stands mostly unaffected by the attack, forcing Jason and Dahlia to seek refuge in a nearby church. Inside, Jason laments that he has so much he wants to share with Dahlia, yet so little time. Grabbing hold of him, Dahlia says she doesn't need words and the pair kiss just as monsters storm the church. As Jason fires his weapons, Dahlia reveals an unseen side of herself and stands transformed, ordering both Jason and the monsters to halt, which they all do. Handing Jason her physical heart, Dahlia tells him to keep it safe, because as long as it's in his protection, he'll be kept safe from the creatures of Silent Hill. She then throws him out of the church, where he lands at Aaron's feet.

Aaron, standing over Jason, reminds him of their business. The group of undead soldiers walk the man to the city limits of Silent Hill, where Aaron asks about Dahlia's gift. Having listened, Aaron explains the circumstances of the attack on their unit, a set up. He tells Jason that it was he, Aaron, who was supposed to be the one to survive. However, the unit felt Jason was the best man among them and deserved a second chance at life. Aaron gave up his own life so Jason could live, and he expected Jason to do just that.

The scene shifts to the mountain range Jason had been trying to reach before entering Silent Hill. Jason and Dahlia stand side by side, her gift having saved both of their lives. Jason explains his encounter with Aaron, but voices doubt about knowing how to truly live. Dahlia has the same doubt, but says they can try together.

Trivia

 * While it seems apparent that both Jason and Dahlia survived Silent Hill, Dead/Alive, which attempts to bring closure to both Among the Damned and The Grinning Man, only confirms Dahlia as having survived.