- Ash's Happy Place in his vision quest is an idealized version of Jacksonville, Florida — a place he was planning to visit with his girlfriend before he went up to that cabin in the woods and his life went to shit. He's never been able to bring himself to go since.
- The very fact that Ash's only ambition in life has been so modest: to live in an unremarkable but pleasant city where he can drink beer, meet pretty girls, and go fishing. And he can't even have that.
- In "A Killer of Killers", a boy who looks no older than about 12-13 is grabbed and thrown by Amanda's newly-possessed-sergeant, getting brutally twisted up into a metal ceiling fan (marking the youngest death in the series so far). Ash looks horrified and lets out a Big "NO!" as he's helpless to intervene.
- The Ending of "Fire in The Hole" where Ash tells the others they hold a special place in his heart and makes a stealth exit while the others keep walking. He heads to the cabin by himself. and doesn't want the others to get involved in it
- Amanda's death in "Ashes to Ashes". Since she was genuinely likable, and up to this point it had seemed like the main cast might literally be invulnerable due to Plot Armor, this came as a hell of a shock.
- The Deadites taunting Ash by appearing to him as Linda's severed head. "She" accuses him of not loving her anymore and abandoning her, and then saying that everyone he loves is going to die, again. Although his response to the matter is quite effective.
- Pablo begging Ash for a Mercy Kill in "The Dark One" after he's possessed by the Necronomicon and Ruby uses him to birth new demons.
- Ash's literally doomed hopes of ever forming a lasting relationship: he's clearly someone who's capable of great depths of love, as demonstrated by the fact that he mourned Linda for thirty years. Sure, part of the jerkass persona he develops involves a lot of random sex with women he doesn't really care for, but while it's Played for Laughs it's clearly all part of the defence he's put up against the trauma he's dealt with. Over the course of the series, he develops a genuine interest in Amanda, whom he actually has a good rapport with and seems to regard as a potential romantic partner, rather than just finding her sexually attractive. She dies in the same room as Linda did, right after they admit their feelings to one another, at the hands of Evil!Ash. The implication that not only is Ash still, deep-down, the gentle and caring kid who really wanted to love someone, but that after decades of suffering he might have been able to regain something of that, only to immediately lose it again - possibly because he is personally cursed - is just brutal.
- "Home" reveals why Ash has spent years drifting from one town to the next: everyone in his hometown thinks he just went crazy in the cabin and killed everyone, dubbing him "Ashey Slashy." It's one thing to be jeered at in a bar, but it also destroyed his relationship with his father (who Ash says turned his back on him). And just to pile on the tragedy, Ash's mother is long dead, so he had no reason to go home until now.
- Ruby, of all people, earns this when Ash kills one of her children. They turned on her and needed to be fought, but she's still devastated.
- In "The Morgue," the group returns to the homestead and heads up to Ash's room. In the hallway, though, Ash spots Cheryl's door and becomes lost in thought over what happened to her. It takes a moment for him to snap out of it. Also, from the look of the door, it's implied no one's stepped foot in her room since she died.
- In "Last Call", Ash and his father finally chew each other out, and it's made clear that Brock is fully convinced that Ash is indeed a psychopath who killed his own sister. Ash is clearly devastated by this. They appear to reconcile when Ash saves Brock from a Deadite... but then he's run over and killed by the possessed Delta before he can even finish apologizing. You also have to feel sorry for the Sheriff's daughter. She clearly didn't relish the idea of stealing Ash's car, unlike the rest of her friends, and yet she's the one who ends up trapped inside it when it gets possessed, and is forced to watch it hunt down and kill her friends, and boyfriend. Especially the latter, with whom she barely has time to exchange "I love you"s before he's killed.
- Though it's mostly played for laughs, the montage of Ash bonding with his Delta, including flashbacks from the original movies,combined with the genuine hurt and shock in his voice when he finds out his beloved car is possessed, really tugs the heartstrings.
- Baal's relentless Mind Rape of Ash in "Delusion". What really sells it is that for at least a while, it almost seems like Baal isn't just toying with him, and that everything Ash thought he knew for the past 30 years was actually all in his head. By the end, Ash submits to Baal's "therapy", allowing himself to become an Empty Shell. Fortunately, the following episode reveals that this isn't the case, and he was just playing along with Baal to get him in the same room as Pablo.
- In "Ashy Slashy" both Pablo and Lacey die in trying to defeat Baal. Baal had kidnapped Lacey, had her forcibly possessed by a deadite and she was put down by Kelly, who laments that Lacey was a good kid. Pablo dies when glass from the window slices him in half during the ceremony. Ash, Kelly, Linda B. and Ruby congratulate him when they send Baal back to the underworld, until he falls down, bisected.
- Also in the promo for episode 9, Ash is shown clearly distraught. Having already lost his sister Cheryl (twice), Shelly, Linda A., Scotty, Annie, Amanda, Heather, his father Brock and Chet (the latter three just in the last few episodes of both seasons) but now losing Lacey and Pablo (The former who was an innocent girl accidentally caught up in the mess and the other his best friend/surrogate son) has clearly taken it's toll and he's now off the deep end.
- More than one in "The Mettle of Man", the show's Grand Finale:
Ash: Oh, great. I've doomed humanity. Yeah, well... not like I didn't tell 'em. Pablo, how may times you heard me say this, huh? Why me?! Who am I?! Nobody. Nobody! Guy from Elk Grove, Michigan. Where the fuck is that? In the middle of jack-shit nowhere, that's where! You know what? I got news for you. I didn't ask for this! You think I want this horse shit? Be covered in blood 24/7? Who the fuck would want that?! Savior, my ass! I'm a... a goddamn failure.
- The Dark Ones have summoned Kandar the Destroyer to destroy the world, and the gang discovers that the demon outbreaks have gone global. Ash promptly goes into a Heroic BSoD and starts getting drunk while ranting about how It Sucks to Be the Chosen One, even sounding on the verge of tears:
Brandy: Dad, get in.Ash: (Takes one Long Last Look at Brandy, Pablo and Kelly before shutting and locking the door)Brandy: No! What are you doing!?Ash: My father always said I ran from my fights, Brandy. I'm not running from this one.Kelly: Ash, come one. Get in the fucking truck!Ash: Kelly, people are going to need a strong leader. Someone they can depend on. Someone they can believe in. That's you. Pablo, you're the "Jefe" now. You save them. (Gestures towards civilians)Brandy: You said you wouldn't leave me!Ash: I'm doing this for you. I'm doing it for all of you. I've got to finally, for once, own up to who the hell I am.
- Ash locks Pablo, Kelly and Brandy in an evacuating army transport. He says a heartfelt goodbye to his kids before going off to face Kandar alone.
Tear Jerker / Ash vs. Evil Dead