Silent Hill owned and published by Konami.

Do your sins weigh heavily on your shoulders? Then you might want to avoid Maine. A survival horror series that examines its characters' psyches as much as it throws monsters in their faces, Silent Hill is one of the more cerebral gaming franchises released in the last three decades. The majority of the games take place in the titular town of Silent Hill, a crumbling, misty, rusting den of nightmares, and the few characters who manage to make it out alive are changed forever. Get ready for some scares.

Depending on who you talk to the 'canonical' games may range from almost every title to only the original, numbered games (1 to 4). The chronology of events is further complicated by Silent Hill: Origins, which contradicts elements of the earlier games, and Silent Hill: Shattered Memories, which is considered to exist in an alternate universe despite being a remake of the original game. You can play as many or as few as the games as you like, but the most cohesive experience (assuming you care) is sticking to the original four.

Although the majority of Silent Hill consists of video games, there are a few movies and comics that reimagine or expand on the events of the games. The films have no bearing on the events of the games, and are only found under Release Order. There are also a few pachislot games which are not included on the timeline, as they are adaptations of existing games. 

In-Universe Chronological Order
Release Order (video games)
Release Order (films)