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Led by Alex Calabrese, Boston-based indie-folk band Old Tom & The Lookouts blend the introspective grit of Americana with the emotional rawness of indie rock. Known for their brooding lyrics and powerful storytelling, the band explores themes of mental health, love, and resilience. Drawing influences from artists like Tom Waits, Frightened Rabbit, and Phoebe Bridgers, Calabrese’s evocative vocals and poignant songwriting strike a chord with listeners searching for authenticity and emotional depth.