Under 1935 Congressional law, monthly Social Security benefits were to start in 1942, in the form of a single, lump-sum refund payment. However, payments of monthly benefits began in January 1940 and not in 1942. On January 31, 1940, the first monthly retirement check was issued to retired legal secretary, Ida May Fuller, of Ludlow, Vermont, in the amount of $22.54. During her 35 years as a beneficiary, Fuller received over $22,000 in benefits.
The early 1940s film from the US Federal Security Agency titled Your Social Security: How the system works gives a good visual history of the subject.