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Gleason was born at 364 Chauncey Street in Bedford-Stuyvesant, Brooklyn, New York. He grew up nearby at 328 Chauncey Street, an address that he later used as the address for Ralph and Alice Kramden on his show The Honeymooners. Originally named Herbert Walton Gleason, Jr., he was baptized as John Herbert Gleason. His parents, both from Farranree, Cork, Ireland, were Mae (Maisie) (née) Murphy, a subway change-booth attendant, and Herb Gleason, an insurance auditor. Gleason was one of their two children. Gleason's brother, Clemence, died of spinal meningitis at age 14, and his father abandoned the family. He remembered his father as having "beautiful handwriting", as Herbert Gleason often worked at the family's kitchen table writing policies in the evenings. The night before his disappearance, Gleason's father disposed of any family photos he was pictured in; just after noon on December 15, 1925, Herbert Gleason collected his hat, coat and paycheck, leaving the insurance company and his family for good. When it was evident he was not coming back, Mae went to work taking change for the Brooklyn–Manhattan Transit Corporation (BMT). After his father left, young Gleason started hanging around on the streets with a local gang and hustling pool. He attended elementary school at P.S. 73 in Brooklyn. He attended but did not graduate from John Adams High School in Queens and Bushwick High School in Brooklyn. Gleason was raised by his mother, who died when he was 19. Gleason became interested in performing after being part of a class play; when he left school he got a job as an MC of a theater. The job paid $4 per night. Other jobs of his included working in a pool hall, stunt diver, and carnival barker. Gleason and his friends made the rounds of the local theaters; he put an act together with one of his friends and the pair performed for Amateur Night at the Halsey Theater, where Gleason replaced his friend, Sammy Birch, as the master of ceremonies. He was also offered the same work two nights a week at the Folly Theater.

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When his mother died in 1935, young Gleason had nowhere to go and less than 40 cents to his name. The family of his first girlfriend, Julie Dennehy, offered to take him in but Gleason was headstrong and insisted he was going into the heart of the city. His friend, Sammy Birch, made room for him in the hotel room he shared with another comedian. Birch also told him of a one week job in Reading, Pennsylvania that would pay $19; it was more money than Gleason could imagine. The booker advanced him bus fare for the trip against his salary; this was Gleason's first job as a professional comedian. He had regular work in a variety of small clubs after that.

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Gleason worked his way up to a job at New York's Club 18, where insulting its patrons was the order of the day. Skater Sonja Henie was greeted by Gleason's handing her an ice cube and saying, "Okay, now do something." It was here where Jack Warner first saw Gleason, signing him to a film contract for $250 per week. By age 24, Gleason was appearing in movies, first at Warner Brothers as Jackie C. Gleason in such films as Navy Blues (1941) with Ann Sheridan and Martha Raye and All Through the Night (1941) with Humphrey Bogart; then at Columbia Pictures for the B military comedy Tramp, Tramp, Tramp (1942); and finally, at Twentieth Century-Fox, where Gleason played the Glenn Miller band's bassist in Orchestra Wives (1942). Gleason also had a small part as the soda shop clerk in Larceny, Inc. (1942) with Edward G. Robinson, and a modest part as "Commissioner" in the 1942 Betty Grable/Harry James musical, Springtime in the Rockies.