It's all your fault and you're gonna' pay for it. 
- ― Nightingale to Alan
Agent Robert Nightingale was a former federal agent pursuing Alan throughout the events of Season 1. He was one of the major antagonists as he frequently tried to arrest or injure Alan, for reasons of his own.[1]
Biography
Background
Robert Nightingale was an federal agent in the FBI. In the past, he had a partner named Flynn, and the two always worked together. They were known as "The Righteous Brothers", due to the fact that they never drank and never went against the rules. But one day, Flynn started talking about "darkness" and he would avoid shadows whenever he could. Nightingale told Flynn to get his act together, but one day, Flynn was "taken" by something. Nightingale became obsessed with finding out what Flynn meant, and he started to take to large bouts of drinking to wash away the guilt he felt for his friend's death. At one point, Nightingale began having terrifying nightmares, similar to the ones Clay Steward and Alan Wake were having. In his dreams, Nightingale saw a man who very closely resembled Alan Wake. Soon, Nightingale became completely obsessed and paranoid about finding the man in his dreams.[2]
Nightingale was acting as a rogue agent in Bright Falls, having been fired from the FBI for unknown reasons prior to the events of Alan Wake. Clay Steward - the writer of the Alan Wake Files - speculates that Nightingale was drawn to Bright Falls in a similar fashion to how Steward was. arrest Alan Wake.[3] Although his precise motivation for his pursuit is uncertain, it is clear that he had discovered the effects of Alan's manuscript on future events. Nightingale was an example of the loose-cannon cop: drunk and trigger happy. On two occasions he tried to shoot at an unarmed Alan, who was standing only a few feet away from civilians.[4]
Searching for Alan Wake
Nightingale is first seen at the trailer park in Episode 3, having been called in by Randolph, the trailer park owner. He has been in Bright Falls for an unknown amount of time, but he has been investigating Alan for a while.
Nightingale across a fence from Alan, aiming a revolver at him. He tells Alan to put his hands in the air, but opens fire when Alan makes a break for the fence. Nightingale almost hits Alan a couple of times, but fails to take the writer down. He almost hits Randolph a few times in the process, and shows no responsibility for doing so when he is scolded. In rage, he sends all the local police forces after Alan, but still fails to apprehend his target. We see Nightingale next outside of Pat Maine's radio station, having tracked down Alan. But once again, he fails to catch the writer, and almost hits Pat Maine. In anger and humiliation of having lost the writer again, he cries out a threat to Wake that he will catch him even if it kills him.
Finally, he manages to catch the writer. Nightingale finds Wake and Barry passed out on a couch in the Anderson farm from moonshine. Despite heavy thought into ending Wake right there, Nightingale brings Wake and Barry into custody.
Having brought Wake into custody, Nightingale taunts Wake repeatedly. He presents a large amount of manuscript pages he has found, and tells Wake that he will be going to jail for a long time. But when an arguments arises, Nightingale lets his guard down. He says a line that was said from a manuscript page by himself. On cue (Much to Nightingale's obvious dismay), the Dark Presence pulls Nightingale out the door. This act supposedly "touched" him but not enough to Take him.
At the end of the game, you can catch a glimpse of Nightingale looking at Rose Marigold from behind a store
Nightingale at the end of Departure
window. Nightingale does not speak, but simply looks on darkly and coldly, alluding to the possibility of Agent Nightingale becoming the new avatar of the darkness.[5]
Manuscripts
Nightingale's Arrival
Agent Nightingale didn’t want to be in Bright Falls. These little communities revolted him. And he didn’t like the trees or the coffee. He now knew that impossible horrors lurked behind the storefronts and smiles.
He desperately wanted to turn the car around and just drive until he passed out or ran out of road and booze. But he had a job to do; he had a writer to catch – at any cost.
Nightingale In The Majestic
Even behind the closed doors and curtains of his grimy room at the majestic – the local motel – Nightingale could feel the locals’ eyes on him, the unrelenting pressure of their judgement.
He forced it out of his mind. For all he knew they could all be under Wake’s spell already. You do what you have to do to get the job done.
He took comfort from the bottle in his hand: “Please,” he thought, “just let me get through this.”
Sarah Distrusts Nightingale
Sarah trusted her gut, and her gut said agent Nightingale was an asshole. He felt wrong, and it wasn’t just the smell of stale booze. It was in the way he flashed his badge, pulled rank, the look in his eyes when he wanted answers. Where was Alan Wake? What was this about an accident? Where was his wife? And most importantly, why did she let Wake go?
He wouldn’t answer her questions “Federal business” was all he’d say.
Nightingale Fires At Wake
The FBI agent’s command froze me in place. I considered surrender, it was all falling apart anyway; I could give in, let someone else deal with it.
But it felt all wrong. Call it instinct; his posture, the way he held the gun, he was no friend.
Shots ringing in my ears I leaped for the hole in the fence and stumbled into the darkness beyond.
Nightingale In The Radio Station
Nightingale stared through the broken studio window into the dark woods, he turned around, started to walk out, but Maine grabbed his arm.
“Young man, you almost shot me! You don’t shoot off rounds at people like that. What’s the matter with you?”
Nightingale shook his arm free, marched out. His cheeks burned with rage and humiliation.
Nightingale Arrests Wake
Agent Nightingale stared at the passed-out writer. The man was sleeping off one hell of a night. Nightingale felt a
stab of envy at Wake’s oblivion. But he had a job to do.
He put the gun to Wake’s head. And almost became a murderer. His hand shook and his throat felt tight and dry, biting his teeth, he tried again to pull the trigger, he lost the nerve.
Wake stirred. Nightingale would have to settle for an arrest.
Nightingale Finds The Manuscript
As the deputies hauled Wake and Wheeler away, Agent nightingale eagerly examined the stack of papers Wake had been carrying.
It was incomplete, a collection of random pages.
But there was enough: he saw his own name in there, among others. His hands shook with emotion.
Finally, it was proof. He had been right all along.
Nightingale Reads The Manuscript
Nightingale tried to make sense of the manuscript. It was disjointed and strange. He didn’t understand half of it, but it all rang true. He took out his hip flask when he reached the page that described how he reached the page that made him take out his hip flask.
It wasn’t the booze that made his mind reel.
Wake And Barry In The Cell
I stared through the bars of the jail cell, Barry stood behind me, swaying on his feet, looking as ill as I felt.
Agent Nightingale stood on the other side of the bars with sheriff breaker. Nightingale had a stack of manuscript pages in his hand. He seemed unhinged as he gloated:
“Well, I’ve got you now, Raymond Chandler. It’s all here, all the evidence, including conspiracy to murder a federal agent.”
Nightingale Attacked By The Dark Presence
Nightingale is swept up by the Dark Presence.
Nightingale felt the situation veering out of his control, but the gun at least felt steady in his hands. He was ready to fire, resolved that he would let this happen over his dead body – and yet he hesitated.
He had seen this moment before, read it in the page. He was transfixed by the déjà vu and the horror that he was a character in a story someone had written.
Then the monstrous presence burst in behind him and dragged him into the night.
Trivia
- When speaking to Alan, Agent Nightingale likes to use the names of other famous writers. He calls him Stephen King, H.P. Lovecraft, James Joyce, Mickey Spillane, Raymond Chandler, Dan Brown, Bret Easton Ellis, Poe and Hemingway. Apparently he is well informed when it comes to literature.
- Much like Rose Marigold, Nightingale seems to have been "touched" by the darkness and not fully taken. In one of the game's last scenes, he can be seen in the shadows behind Rose. This creates the question of whether Nightingale has been chosen to replace Barbara Jagger as the face of The Dark Presence. This would be sensible, as Alan did not seem to specify the exact fate of Nightingale - only that he was attacked. A manuscript seems to also support this, explaining how the darkness could take advantage of what the writer failed to write about. However, it is also possible that Alan himself wrote this into the manuscript after he entered the cabin again in Episode 6, playing into what he mentioned as everything having a price, and that now balancing the scales, so to speak, was where Thomas Zane had gone wrong in the past. Thus, perhaps in order to prevent a revived Alice from turning into what Barbara Jagger was, he instead gave that role to Nightingale. Also, before Barbara's heart was filled with light, she did say "I will find a new face to wear".
- Nightingale may have been drawn to Bright Falls looking for Jake Fischer. He may have been attracted to Jake's disappearance, along with Sam Smith's.
- There is an Xbox avatar FBI jacket that closely resembles his.
- Nightingale is also the name of Florence Nightingale, a famous English Nurse of the 19th century. She was dubbed "The Lady with the Lamp", like Cynthia Weaver.
- Nightingale's name was likely influenced by The Nightingale a song in the first episode of Twin Peaks.
Unanswered questions
- What happened to Agent Nightingale after he was pulled out the police station by the Dark Presence?
- Is he the new face of the darkness?