Appearances in Alan Wake (Spoilers)
Alan Wake first encounters Nightingale in the trailer park in Episode 3. The local police are called to the scene by the trailer park owner Randolph, who is suspicious of Wake and Barry after they disappeared into Rose's trailer for a long period of time. Agent Nightingale attempts to apprehend Wake, and opens fire on him when Wake begins to escape, narrowly missing both Wake and Randolph. In anger, Nightingale sends the Bright Falls police force after Wake, however Wake manages to escape through the woods to the nearby radio station.
It is here Nightingale corners Wake, aiming his weapon at Wake through the window of the radio station. Instead of attempting to surround and apprehend Wake quietly, Nightingale opens fire, showing a complete lack of regard for radio presenter Pat Maine, who is in the room with Wake at the time. Again Nightingale shows his determination to take down Alan Wake no matter what the cost.
Nightingale finally manages to track Wake down again, at the Anderson Brothers' farm. At the time, Alan and Barry are passed out from drinking the Anderson Brothers' moonshine. It is revealed through manuscript pages that Nightingale had been contemplating shooting Wake in cold blood, but resigns himself to simply making an arrest when Wake rouses from his sleep.
Back at the police station, Nightingale takes his time to taunt Wake behind bars. Nightingale has discovered the manuscript pages Wake was carrying, and tells Wake he's going to jail for a long time. During an argument between Nightingale, Sheriff Breaker and Wake, Nightingale realizes he is acting and speaking exactly as a manuscript page had described. As Nightingale tries to find the page amongst the stack of papers, the Dark Presence bursts forth from the door and drags Nightingale out into the dark.
It is thought that Nightingale perishes at this point, however he is shown one last time during the ending cinematic of the game. The scene shows Bright Falls, somewhat returned to order after the events in the game. Rose Marigold is shown out in the sunlight, holding Cynthia Weaver's old lamp. Behind her, Nightingale is watching, lurking inside a house in the shadows. This scene has given rise to the belief that Rose is the new Lady of the Light, and Nightingale has become host to the Dark Presence.
- Nightingale's character is often used as comic relief throughout the game. Whenever he speaks to Wake, he calls him by a different name, which is always based upon a famous author. The following names are used by Nightingale throughout the game to reference Alan: Dan Brown, H.P. Lovecraft, Raymond Chandler, Stephen King, Mickey Spillane, Ernest Hemingway, James Joyce, and Bret Easton Ellis.