Plaintive

The plaintive melody broke her heart.

Tom has such a plaintive quality to his singing voice that even his happy songs sound sad.

Nine hundred years shall you wander over the lakes and streams of Erin. This only I will grant unto you: that you retain your own speech, and there shall be no music in the world equal to yours, the plaintive music you shall sing.

Then his plaintive tone / no more could Venus bear, but interrupts her son: / "Stranger", she answered, "whosoe'er thou be; / not unbeloved of heavenly powers, I ween, / thou breath'st the vital air, whom Fate's decree / permits a Tyrian city to have seen."

The maniacs tore him limb from limb, and threw his head and his lyre into the river Hebrus, down which they floated, murmuring sad music, to which the shores responded a plaintive symphony.

“Yes,” replies the fisherman, “I have seen the white daughter of the sea, and I have heard her sing, and her songs were plaintive as the sound of the waves.”

He accompanies his songs with plaintive chords played on a poor-quality zither.

The cat let out a plaintive meow.

The puppy shot a plaintive look at his owner when he saw they were going to give him a shot.

For his birthday, Mary gave Tom a new leaf blower, the old one having given up the ghost some time ago. Their neighbour, witnessing the scene, threw his hands up and let out a plaintive cry.