Corruption or Crimson decides which evil boss your world has: the Eater of Worlds or the Brain of Cthulhu. The Wall of Flesh flips the world into Hardmode, and that's where the bigger bosses begin.
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Pre-Hardmode
Hardmode
The Eater or Brain depends on your world
A standard world generates with one evil, Corruption or Crimson, and that decides whether you can summon the Eater of Worlds or the Brain of Cthulhu. Each boss drops ore for gear tied to that evil: Demonite from the Eater, Crimtane from the Brain.
The early bosses you can take in any order
King Slime is the friendliest first fight. You can call him with a Slime Crown whenever you like, and his drop pool includes a mount worth the trip.
The Eye of Cthulhu often shows up on its own. If you're not ready for it, stay underground until you are.
Queen Bee waits in the Underground Jungle, where a Larva inside a Bee Hive is one way to call her. Her defeat lets the Witch Doctor move in, which makes her a useful detour.
Deerclops is optional, and nothing later gates his summon.
Skeletron opens the Dungeon
The fight starts when you talk to the Old Man at the Dungeon entrance at night and choose the curse. Once Skeletron falls, the whole world gets full Dungeon access, and the Clothier can move in.
The Wall of Flesh flips the world
Drop a Guide Voodoo Doll into Underworld lava to start the fight. Once the Wall falls, the world stays in Hardmode for good, and the Hallow starts spreading beside your evil in diagonal stripes. The Pwnhammer it drops is required to generate Hardmode ore, so keep it.
Queen Slime is an optional early Hardmode fight. A Gelatin Crystal calls her inside the Hallow at any time of day.
The mechanical bosses, then Plantera
The Twins, The Destroyer and Skeletron Prime can go in any order. Each has a night summon, and each can also spawn on its own after you break a Demon or Crimson Altar. All of them need to fall before Plantera's Bulbs grow in the Underground Jungle, so plan for the three together.
Plantera is the gate to the jungle temple. Her Temple Key opens the Jungle Temple, and the Lihzahrd Power Cell there is what summons Golem after she falls.
Golem, the Cultists and Moon Lord
Golem's defeat brings the Cultists to the Dungeon entrance. Kill them and the Mysterious Tablet they leave summons the Lunatic Cultist, which needs Skeletron and Golem both down first. The Lunatic Cultist starts the Lunar Events, and once the Celestial Pillars fall, Moon Lord arrives. If you'd rather skip the pillars, a Celestial Sigil does the job once Golem is down.
Optional fights to take on your terms
Duke Fishron is optional once you reach Hardmode, and he's the reason to fish the Ocean. The Empress of Light needs a Prismatic Lacewing from the surface Hallow, and her daytime enrage is the part to plan around.
Expert and Master raise health on every boss, and several fights play differently. The Brain gains mirror images, Skeletron's head fires homing skulls, and the Twins' eyes fire faster. Those changes are worth a look before you go in.
Where to go after the bosses
Several of these fights bring residents to your town: the Dryad after the Eye of Cthulhu, the Witch Doctor after Queen Bee, and the Cyborg after Plantera. The Terraria NPCs page covers who moves in and what they sell, and the Terraria biomes page shows where each of these fights happens.
FAQ
Can I fight Duke Fishron before the mechanical bosses?
Yes. Hardmode is his only requirement, so a Truffle Worm used while fishing in the Ocean is enough to call him. He has 60,000 HP in Classic, and Expert and Master add a third phase, so bring your best Hardmode gear.
Why did an Eye of Cthulhu show up without a Suspicious Looking Eye?
At dusk, the game gives the Eye a one-in-three chance to queue a natural spawn if at least one player has 200 max health and 11 defense, at least four town NPCs live in your world (town pets count, the Skeleton Merchant doesn't), and no boss is alive. If you've already beaten it, natural spawns stop while a Demon or Crimson Altar is placed. The delayed spawn needs a player at the Surface or Space layer, so staying underground prevents it.
Can I summon Skeletron again after I've beaten him?
Yes. The Old Man's curse only works before the first win. After that, equip a Clothier Voodoo Doll and kill the Clothier at night to bring him back.