Well I tried it to see if it works on PS3 and it does. Mud214, I know why your jumps were failing. The roof on that little section is slanted, so when you jump when your close to the wall your gonna hit your head and come back down. Thus, you have to move a little to the right on the barrel. Just enough so that your still on it and when you jump without moving your not restricted. After that you'll get on the wall every time.
On another note, the items you get in this chest (Eorland's Chest) is based on your level (may be smithing) I believe. Also if you joined the Companions, Wolf armor and Skyforge Steel weapons will be available in the chest.