Seemingly born an old soul, New York–by-way-of-Houston singer Jolie Holland spins a weary timelessness into everything she puts her name to. Traditional folk, jazz, and country-blues run through her songs, all loosely framed with a hipster vibe, and her voice is the kind of elastic warble you might get if you blended Billie Holiday with Maybelle Carter. Though Holland was one of the founding members of the chirpy Vancouver folk trio the Be Good Tanyas, she didn’t last long there. Her solo work, which hit a peak on 2004’s dazzling Escondida and has been a bit uneven since, veers more toward the melancholic, which is in full display on her fifth album, Pint of Blood (Anti-). “If disappointment was like a drug, I overdosed again,” she sings on “Wreckage,” an “I’m moving on” shuffle that’s both sad and affirming. So it goes with Holland’s songs; lyrics start out one way and end another, and nothing very dramatic happens in between. The delights she offers—a turned phrase, a twisted inflection, off-kilter melodies—are small and subtle. Her band (multi-instrumentalist Shahzad Ismaily plays and co-produces here, as he did on Holland’s previous record, The Living and the Dead ) maintains a steady mid-tempo throughout, which might make it challenging to listen to Pint of Blood all the way through. But if you give yourself over to the album, it’ll pull you in. This is an entrancing downer of a record, so much so that the closer, a stark cover of Townes Van Zandt’s “Rex’s Blues,” feels almost superfluous.