Old Man Logan is an eight chapter story set in an Alternate Universe / Bad Future where the villains of the Marvel Universe took over the United States and divided it up into territories. A now pacifist Logan lives with his new family in "Hulkland" (formerly, The Abomination's Territory, formerly California) where the inbred children of an evilHulk are the lords of the land. Logan is short on the rent, and must team up with a now blind Hawkeye to deliver a mysterious cargo in order to help keep his Landlords from killing him and his family.
Bittersweet Ending: Logan's family have been killed by the Hulk Gang, but on a positive note the Hulk Gang and Red Skull are dead, and Wolverine is forming an Avengers team. If Old Man Logan does become the Hooded Man that appears in a Fantastic Four miniseries (as is heavily implied), then the future looks even better.
Blind Weaponmaster: You would think that Hawkeye being blind now would effect his ability to shoot arrows. You'd be wrong.
Hawkeye "That's right, bitches. Just keep making noises!"
Book Ends: For Wolverine overall. He was first introduced in an issue of Incredible Hulk, facing off with the titular green giant. This (possible) finale of his story and character development ends with him facing off against the Hulk and his inbred gang.
Broken Hero: The reason Logan hasn't popped his claws in fifty years? "They broke me, Bub" They really really did.
Cannibal Clan: You'll notice the Hulk Gang's food of choice is human limbs.
Car Fu: "It's the Spider-Buggy, dude. She can take her share of knocks"
Chekhov's Exhibit: Wolverine and the Red Skull fight in a room full of trophies taken from dead superheroes. The latter wields Black Knight's sword, while Wolverine uses Captain America's shield and pieces of Iron Man's armour.
Corrupt Hick: The Hulk Gang counts as this very much, even though they are located in California. The Hulk himself is the corrupt hick leading them and in charge of a territory called Hulkland. They are violent and quite murderous, considering how they murdered Logan's family and left the bodies unburied while he was busy trying to pay off a debt he owed them. Why? Because they got bored. They are a family of cannibals. Oh, and they are also inbred, because Hulk raped his own cousin Jennifer more than once to form the Hulk Gang!
Covers Always Lie: The cover of issue 2 shows Hammer Falls as being Thor's hammer surrounded by the costumed bodies of other heroes defeated there. In the actual issue it's just Thor's hammer, and most other heroes' remains are later shown to be in Red Skull's trophy room.
Crapsack World: Brought to you by President Red Skull! Not much is said about the world outside of the USA, but Red Skull implies that it's even worse off.
Dug Too Deep: Moloids have become a not uncommon problem, as the subterranean dwellers have started digging up to the surface in order to get away from the things they awoke when they invoked this trope. Presumably, some heroes (probably the Fantastic Four) would have gone on an adventure to the Inner Earth and solved the problem for the Moloids when it started, but they were all, you know, dead...
Enfant Terrible: Dwight, who uses the Ant-Man helmet to extort a fare for crossing a bridge. Anyone who doesn't pay gets devoured by ants.
Evil All Along: Ashley Barton, the granddaughter of Spider-Man turns out to be as evil as her father thought she was and just wanted to kill the Kingpin so that she could replace him.
Evil Old Folks: Bruce Banner, Red Skull, Dr Doom and really any of the original supervillains who are still ruling.
Evil Power Vacuum: It's safe to assume a lot of this goes on. After all, there's a different Kingpin now who apparently didn't have much trouble killing Magneto.
Killed Off for Real: Before the story starts nearly all of the heroes are dead, including all of the X-Men, as are several villains including the original Kingpin, Magneto (by the second Kingpin), the Abomination and Loki.
In story, Red Skull, the second Kingpin, Hawkeye, Punisher, Daredevil, Bruce Banner, Logan's family and most of the Hulk Gang.
Lamarck Was Right: Played straight with the Hulk Gang, which is made up of Hulk's inbred offspring, but averted when it comes to mutants. Apparently, mutants in this continuity weren't the promised next stage in human evolution, just a "brief genetic anomaly". Notably, Logan's children lack a Healing Factor.
Legacy Character: Peter Parker's grandaughter, who becomes Spider-Girl and the third Kingpin. Her allies Punisher and Daredevil are probably not the originals too.
The Ghost Riders are a biker gang with skulls painted on their faces and flaming wheels on their bikes.
No Doubt The Years Have Changed Me: Most of the remaining super heroes of the old days aren't what they used to be, and neither are some of the villains. Double subverted with Emma Frost, who appears the same age, but is actually using her telepathy to hide her aging.
Averted with Red Skull. He hasn't changed a bit.
Not-So-Harmless Villain: Who was the one who broke Logan and effectively destroyed the X-Men? Fucking Mysterio. And it's implied it wasn't even the original, but the third.
Offscreen Moment of Awesome: So many from the war the villains won. Highlights include Magneto and Absorbing Man killing Thor, and whatever killed Loki when he was as tall as a skyscraper. Hawkeye even lampshades the latter one.
Off with His Head!: Spider-Girl takes off the second Kingpin's head with a shotgun handle.
Also how Logan finishes off the Red Skull, with Cap's shield no less.
Oh Crap: Hulk when he remembers what one of Logan's mutant abilities is regeneration after eating him. Needless to say, it did not end well for Hulk.
That Man Is Dead: After Wolverine finds out he murdered the X-Men, he runs for a railroad track and lets a train run over him. Since adamantium skeleton and healing factor are still there, he's still alive, but he considers himself dead.