Why this works:
Much like No Country for Old Men, The Departed would be a big departure from the usual type of games that Telltale produces. Most of the games on this list exist in a very clear world of fiction. The events of Die Hard would probably not occur in real life. Nor would those of The Thing, The Raiders of the Lost Ark, or The Terminator.
The Departed, however, has events that feel possible. It would be tough for Telltale to tackle these kinds of characters and situations, especially with such adult materials, but I think it would make the game so much more interesting if handled correctly. There's plenty of gameplay opportunities there, so its up to the writers to show that they can deal with a story like this.