Listening to RIOT SON’s new single, “Loneliest at Best,” is a curious exercise in emotional time-travel. The sound pulls you back to the early 2000s, to a time of angular guitars and heartfelt, frayed-collar vocals. It has that nervous, shimmering energy of indie rock that always sounded best on a pair of wired headphones, the beat prodding you forward even as the lyrics confess...

To understand a song like “Over And Over,” you first have to understand the road it travelled to get here. This is not a track that sprang fully formed from a young artist’s ambition. It’s a gnarled, weathered thing, carrying the dust of a long and winding path. The artist, Block, is a name that echoes from the raucous, DIY-spirited New York anti-folk scene of...