While Terraria 1.4.5’s Bigger and Boulder update didn’t really add any brand new boss fights, there is one unique boss encounter that does have a new vanity set to accompany it. This is Chippy Skeletron, a boss made in tribute to the YouTuber ChippyGaming.
The way to summon this boss is very unconventional and is something you’re likely only going to figure out by reading a guide on it. It requires that you have at least beaten Skeletron once and have gotten some loot from the Dungeon he was guarding.
Once you’ve cleared those prerequisites, you’re ready to get the setup ready and take on Chippy Skeletron!
Setting Up

There are two main items you will need for this fight, those being Chippy’s Couch and the Clothier Voodoo Doll. Getting the couch is simple, as it’s a drop from Skeletron and is rather common. If you didn’t get it on your first try, though, you’ll need to get the doll first.
The Clothier Dolls drop from enemies in the dungeon at random, at a 0.33% drop rate from Angry Bones and Dark Casters. For this reason, I’d recommend waiting on grinding this out until early hardmode, as you’ll easily tear through enemies at that point.
To farm enemies somewhat more efficiently, carve out a large part of the Dungeon to act as a pseudo mob farm, then let the enemies come to you. This process can be further sped up by adding lava onto a roof above you and sitting cozy in a box where you can barely be hit.
Once you have the doll, if you didn’t get the couch, you can equip it and kill the Clothier at night to summon Skeletron, then re-fight him until you get Chippy’s Couch. With these two things and the Clothier in a home, you can fight Chippy Skeletron.
Fighting Chippy Skeletron

To summon Chippy Skeletron, place Chippy’s Couch in eyesight of the Clothier, then, at night, equip the Clothier Voodoo Doll and sit on the couch. This immediately summons Chippy Skeletron, so be wary that he can murk your other NPCs, and maybe use your Pylons to move the Clothier.
The fight itself is nearly identical to the standard Skeletron fight, but Chippy Skeletron will throw out a bunch of really funny YouTuber statements and summon some appropriately dressed Dark Casters that can mess you up if you aren’t careful.
I’d recommend fighting him in a decently open space, with enough room for you to maneuver and take out the casters as they spawn. They can be rather annoying in this fight, which you’d be familiar with if you’ve ever fought Skeletron in the For the Worthy secret seed.
As is usual for Skeletron, try to take out his hands first if you’re in Expert or above, and be incredibly cautious once his head spins, as it can take you out in seconds. After taking out the head, you will be rewarded with Chippy’s vanity set and some inactive wings.
Activating The Wings

The main reason why I suggest doing this in early hardmode is that you need 20 Souls of Flight at a Mythril or Orichalcum anvil to fix Chippy’s Cloak. Once you do, though, they become equivalent to a set of dev wings and are arguably the best wings to get in this stage of the game.
They have a flight time of 2.5 seconds, go up to 77 tiles, and can fly somewhat quickly, making them better than the commonly used Fairy Wings, and far superior to the Demon or Angel wings that are usually an easy early hardmode choice.
