If $\partial(u \smile w) = - u \smile v$, then $\partial(-u \smile w) = u \smile v$.
Therefore the cup product of a cocycle and a coboundary, in either order, is a coboundary.
If $\partial(u \smile w) = - u \smile v$, then $\partial(-u \smile w) = u \smile v$.
Therefore the cup product of a cocycle and a coboundary, in either order, is a coboundary.