[GoldenAge50s]

I'm positive that's Sinatra.

Here's an excerpt on his career:

1935–40: Start of career, work with Harry James and Tommy Dorsey[edit]Sinatra got his first break in 1935 when his mother persuaded a local singing group, The Three Flashes, to let him join. With Sinatra, the group became known as the Hoboken Four,[5] and they sufficiently impressed Edward Bowes. After appearing on his show, Major Bowes Amateur Hour, they attracted 40,000 votes and won first prize – a six-month contract to perform on stage and radio across the United States.

Sinatra left the Hoboken Four and returned home in late 1935. His mother secured him a job as a singing waiter and MC at the Rustic Cabin in Englewood Cliffs, New Jersey, for which he was paid $15 a week.[12]

On March 18, 1939, Sinatra made a demo recording of a song called "Our Love", with the Frank Mane band. The record has "Frank Sinatra" signed on the front. The bandleader kept the original record in a safe for nearly 60 years.[7][page needed] In June, Harry James hired Sinatra on a one-year contract of $75 a week.[13] It was with the James band that Sinatra released his first commercial record "From the Bottom of My Heart" in July 1939[14]— US Brunswick No. 8443 and UK Columbia #DB2150.[15][page needed] In September 1940, Sinatra, after playing with Tommy Dorsey at Old Orchard Beach Pier, surprised nightclubbers in Portland, Maine, by turning up at the Morocco Lounge. "It was way before he became famous." [16]