Having being born in a farm at Staddle, Billy had grown up as a farm lad. Billy's life at Staddle been peaceful and quiet enough but at recent years, things have somewhat changed... Brigands were moving into both South and North Chetwood, the marshes grow nastier, there were rumors of Archet being burnt up north, troubles were stirring up at the Barrows and there were talk of orcs far north of Bree - more than enough to terrify any hobbit in Staddle!!!

Then, one day Billy's parents - Will Cropper an Poppy Underhill were afraid that all these brigands and evil people would hurt Billy and that they couldn't bear losing their only son. So they decided for Billy to go to the Shire where he could be much safer. And reluctantly he rode to the Shire on Apples without much of an adventure for over a week. But when he did traveled around the Shire that was an adventure and he found many many dangers and troubles while traveling the Shire but that's for later. After a whole month of traveling he finally found a burrow and settled there. And nowadays he just spends time at the Bird and Baby Inn or traveling or simply enjoying a nice meal!