A native of Fredericktown, Ohio, Preston Cooper began making music in high school, when he learned to play the guitar. For a time, he worked as a letter carrier, earning the nickname "The Singing Mailman". Discovered in 2023 at a new talent contest in Toledo, he was spotted by brothers Brad and Brett Warren and signed to Big Machine Records subsidiary The Valory Music Co. at the end of 2024. His first single "Weak", released in January 2025, is quickly adopted by country radio stations, followed by "One More Place I've Never Been", "Numbers on a Mailbox" and "One for the Road", included on the debut album Toledo Talkin'. In June 2025, "Weak" reaches number 59 in the Radio Country Songs charts.
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