I am going to go in the order of the seasons, so first off is Deerclops. Deerclops is the first boss you will encounter, on day 30 (Note that all the winters ahead will have a Deerclops, but it can sometimes glitch and not show up a year.) What I do is I usually gather many blue caps and green caps. Cook the green caps for sanity and keep the blue caps raw because they give a massive amount of health. The reason why you should use cooked green caps is because if you go insane, nightmare creatures will spawn, and no nothing but stall the battle, and possibly kill you. You should at least have from my experience, about 10-20 blue caps and cooked green caps. You should also have 3 log suits and 2 football helmets, in case you get hurt from kiting Deerclops. When you kite Deerclops, it is a little tricky, even for me, because the range of damage is a little broken, but I will try to explain it. You hit Deerclops 2-3 times, then you run away when it raises it’s hand, preparing an attack. Then run back towards it and repeat. You can alse cheese it by going to a setpiece, like the reed trap, and lure Deerclops into it, killing both the tentacles and Deerclops. You can also use beefalo, especially when they are in heat. If you are unlucky and you don’t have any effective setpieces, you can also use tooth traps, bee mines, and gunpowder (don’t forget that if you kill Deerclops with fire it will cook the mean, and burn the eye, turning it into ashes, so if it’s your first winter, avoid using fire weapons because you need that eyebrella for spring.) You can also make sculptures of Deerclops with the eye, but make the eyebrella first.