Hefner was born in Chicago, Illinois, the elder of two sons born to Grace Caroline (née Swanson; 1895–1997) and Glenn Lucius Hefner (1896–1976), both teachers. Hefner's mother was of Swedish descent and his father had German and English ancestry; on his father's side, Hefner is a direct descendant of Plymouth governor William Bradford. He has described his family as "conservative, Midwest, Methodist". He went to Sayre Elementary School and Steinmetz High School, then served as a writer for a military newspaper in the U.S. Army from 1944 to 1946. He later graduated from the University of Illinois at Urbana-Champaign with a B.A. in psychology with a double minor in creative writing and art in 1949, earning his degree in two and a half years. After graduation, he took a semester of graduate courses in sociology and women and gender studies at Northwestern University but dropped out soon after.
Working as a copywriter for Esquire, he left in January 1952 after being denied a $5 raise. In 1953, he mortgaged his furniture, generating a bank loan of $600 (or $800—he cannot recall which) and raised $8,000 from 45 investors— including $1,000 from his mother ("Not because she believed in the venture," he told E! in 2006. "But because she believed in her son") – to launch Playboy, which was initially going to be called Stag Party. The undated first issue, published in December 1953, featured Marilyn Monroe from her 1949 nude calendar shoot. Hefner, who never met Monroe, bought the crypt next to hers at the Westwood Village Memorial Park Cemetery.
The magazine has a long history of publishing short stories by notable novelists such as Arthur C. Clarke, Ian Fleming, Vladimir Nabokov, P. G. Wodehouse, and Margaret Atwood. Playboy
features monthly interviews of notable public figures, such as artists,
architects, economists, composers, conductors, film directors,
journalists, novelists, playwrights, religious figures, politicians,
athletes and race car drivers. The magazine generally reflects a liberal editorial stance.