- When Etrigan the demon fights the alien parasite who gave Tommy his powers at a gangster's funeral (the same gangster that Tommy was hired to kill). Yes, it's exactly as Crazy Awesome as it sounds, and is very funny.
- Tommy puking his curry on Batman's feet. Batman promptly decks him.
- Tommy's first encounter with Green Lantern:Green Lantern: Your murder express just ran out of highway, Monaghan! This is one guy you won't be adding to your bodycount! Time to scratch Green Lantern off your list!
Tommy: Don't you mean railroad?
Green Lantern: What?
Tommy: Well, if it's a murder express, ain't it gonna be on the railroad an' not the highway? Don't see too many trains on the interstate, right? Unless it's an express bus, I guess. Is it a bus?
Green Lantern: What are you talking about?
Tommy: Just curious.
- At the conclusion of the storyarc, Kyle tells Tommy that he still doesn't like him, but then goes off on a lengthy tirade about Gotham being a dark place that might need a dark hero, which gets more wordy and melodramatic. He doesn't even notice when Tommy just leaves in the middle of the speech and just keeps babbling.
- When Sixpack goes to get The Defenestrator, one of his old teammates, out of Arkham Asylum. (Keep in mind that Sixpack is a fat, drunken homeless man in a soiled, ridiculous superhero costume.)Sixpack: He's needed, Doc. Badly. How soon can ya let him go?
Doctor: I dunno about that. We got pretty strict security procedures here at Arkham... On the other hand, you seem like a pretty responsible guy. What the hell, huh? Sign here, here, here, and here and we'll release him into your care.
- The Defenestrator, by the way, is never seen throwing people out of windows. He lassos people by smashing pre-assembled windows over their heads.
- The rhyming narration of the Christmas issue In the Style of... "Twas the Night Before Christmas.""Word!" said his homie, "I got my nine! Now let's go bust a cap in that nuclear swine!"
- Hacken killing chickens.
- Tommy killing a vampire by blowing his arms and legs off with a shotgun and leaving the limbless torso in the street to wait for sunrise. Extra points for the vampire breaking down and bitching and crying like a wuss
- The JLA crossover where, after Batman has angrily informed the rest of the Justice League that Tommy is a hardened, ruthless assassin, Superman — who is unaware of Tommy's profession, has missed this entire revelation and once had a friendly conversation with him on a Gotham rooftop — enters the room and greets Tommy like an old friend. As Tommy and Superman catch up, the rest of the Justice League just gape in astonishment (except Green Lantern, the target of Batman's rant due to working with Tommy previously, who just looks smug).
- Tiegel's confession of virginity to Tommy. After a few minutes pacing on the carpet, trying to work out how to phrase it, Tommy surprises her and...Tommy: "Hi."
Tiegel: "Ah! Monaghan! I've never made sex before!"
Tommy: "...Made sex?"
- In a brief moment of levity before the final bloodbath, Tommy attempts to save Hacken's life with a Tap on the Head.Hacken: "Holy Jeez, Tommy, someone just hit me over the head! Did you see who it was?"
- A second blow from Natt does knock him out, and when Tommy claims that Hacken has a skull like a rock, Natt asks if it wasnt just that Tommy hits like a girl.
- The existence of Dogwelder. (He welds dead puppies onto the bodies of criminals.) Apparently Ennis and his pals were fooling around at a bar one night, someone suggested they play "Name The Dumbest Superhero Ever", and this was the first, only, and winning suggestion.
- Really, just so much about Section 8.Sixpack: That's it, Jean! Hit them with the power of Frenchness!
- Really, just so much about Section 8.
- The very title of Zombie Night at the Gotham Aquarium drips with Bloody Hilarious.
- Despite Ennis's stated dislike for Green Lantern, GL is at least treated with a slight amount of respect for being a well-intentioned moron. When the CIA claims Tommy was hired to kill GL, Tommy gets into a snarky argument with him and cons him into an epic rant while he reads his mind;(So your ring there, what does it do... That. That. That. Holy crap, what doesn't it do?) Catch! throws grenade (It doesn't make you smarter.)
- Not so Lobo; the splash page of the Hitman/Lobo special has him enter Noonan's while saying "Frag, frag, bastich, etc." Ennis's contempt could not be more obvious (or hilarious) throughout the issue. Especially since Tommy's endgame is to sic Section Eight on him - an epicly ridiculous fight culminating in a show-stopping performance by Bueno Excellente, who "fights crime with the power of perversion." More specifically, Bueno "marries" Lobo in front of a camera, then has sex with him. Also on camera. Tommy then says if Lobo ever harms or even bothers Noonan or any of his friends, Tommy will give the tapes to the Justice League and pretty much everyone else who fights Lobo regularly, making him into a laughingstock. Lobo rages, but obeys. Adding insult to injury, Sixpack took a whizz in the gas tank of Lobo's space-motorcycle, making his ride out rather spectacularly humiliating.
- The "Cat-Signal" which is a dead cat laid on a spot light, meant to summon Catwoman. It works, "And I hope it was dead when you found it."
Tommy: Where's the heavy stuff?
- Shortly thereafter Tommy and the gang have to deal with a ten-armed gunslinger demon. Plan A: Drive away forever. Complication: The Mawzir can run at sixty-plus pretty much forever. Plan B?
Tommy: Great. Zee oozi nine millimetah?
Natt: Didn't bring it.
- Tommy smugly telling Natt that he basically checked out Catwoman with his x-ray vision.
- The very open contempt Ennis has for 90s superheroes wouldnt be topped until The Boys decades later. One of the highpoints is one metahuman who can turn anything he touches into a gun accidently mutilating and killing himself with his own powers by shooting himself with a medkit he turned into a gun, and then turned his ass into a grenade.
- There's Skull and Scarlet Rose, two very Dark and Edgy supervillains working as bodyguards for an African dictator, and enacts a ton of atrocities for him. While thats very much not played for laughs, the way they're dispatched is; Scarlet Rose (who's powers are controlling rose thornes) gets run over by a tank, and Skull gets hit point blank range with the tanks cannon. He doesnt even realize he's dead until he looks down and sees that his bottom half is missing.
- The drug-dealing vigilante Nightfist goes after Tommy after he survives his initial encounter with him, but unfortunatly ends up bursting into a showdown between Tommy, Natt and a huge group of mobsters, who immediatly blasts him to pieces.
- The DC One Million tie-in. Tommy gets summoned to the 853rd Century by a crew of dorky kids who thought Hit-Man (yes, like this) was a hero who defended Gotham City along with his "lovely assistant Natalie" (a genderflipped Natt). And it only goes downhill from there.
- During an accidental transportation to prehistoric Earth, Natt has a real streak of misfortune. First he wipes his ass with some sort of proto-poison ivy, and a few minutes later gets bit in the ass by a hungry T-rex.
Funny / Hitman (1993)