“Feels like all I ever do is try / And try again,” Kerrin Connolly sings on “Try”, the first track on her latest album, Simpleton. While the song seems like a monument to self-doubt, the album by the Boston-based singer-songwriter and multi-instrumentalist shows an artist overflowing with chops and dedication. While there are plenty of similarities between Simpleton and previous albums like Almost (2020) and Transitions (2024), Connolly has stepped up her game on her latest record, with smart, sophisticated arrangements and an arsenal of pop songs that are a quantum leap from those already-great earlier works.
Connolly describes Simpleton as “a concept album which explores the themes of a hero’s journey – some classic, others modern and…

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