1. [adj]  affected by or full of grief or woe; "his sorrow...made him look...haggard and...woebegone"- George du Maurier
2. [adj]  worn and broken down by hard use; "a creaky shack"; "a decrepit bus...its seats held together with friction tape"; "a flea-bitten sofa"; "a run-down neighborhood"; "a woebegone old shack"

WOEBEGONE is a 9 letter word that starts with W.