Rabbitt worked as a mental hospital attendant in the late 1950s, but like his father, he fulfilled his love of music by performing at the Six Steps Down club in his hometown. He later won a talent contest and was given an hour of Saturday night radio show time to broadcast a live performance from a bar in Paterson, New Jersey. In 1964, he signed his first record deal with 20th Century Records and released the singles "Next to the Note" and "Six Nights and Seven Days". Four years later, with $1,000 to his name, Rabbitt moved to Nashville, where he began his career as a songwriter. During his first night in the town, Rabbitt wrote "Working My Way Up to the Bottom", which Roy Drusky recorded in 1968. To support himself, Rabbitt worked as a truck driver, soda jerk and fruit picker in Nashville. He was ultimately hired as a staff writer for the Hill & Range Publishing Company for $37.50 per week. As a young songwriter, Rabbitt socialized with other aspiring writers at Wally's Clubhouse, a Nashville bar; he said he and the other patrons had "no place else to go."