What was Bob Dylan's first professional recording? Here’s a hint. It was not on a Harry Belafonte record. Here’s the answer… Carolyn Hester’s self-titled album on Columbia Records. It’s been believed for years that Bob’s first pro appearance on record was playing harmonica on Belafonte’s “The Midnight Special". It’s true that the latter was released before Hester’s album, but Dylan’s performance on Hester’s record was recorded earlier than Belafonte’s record. It was at the Carolyn Hester sessions that her producer, John Hammond, met Dylan for the first time. He quickly signed him to Columbia, and the rest is history!