In March 1952 Bill Wannan distributed the first roneoed copies of Realist Writer to the Melbourne Realist Writers' Group, an organisation sponsored by the Communist Party of Australia (CPA). Planned as a bulletin to share work within the group, Realist Writer sought to develop the genre of social realism in Australian literature. Beginning with the third issue, Stephen Murray-Smith accepted editorial responsibility, producing seven more issues before Realist Writer was incorporated into the first issue of Overland.

The first issue of Overland delared its motto, 'Temper democratic; Bias, Australian', adapting Joseph Furphy's description of Such is Life (1903). According to Murray-Smith, Overland sought to attract a 'mass audience' and he encouraged that audience to contribute to the development of the magazine. The first issue announced that Overland 'will aim high, but has no exclusive or academic standards of any kind. It will make a special point of developing writing talent in people of diverse background. We ask of our readers, however inexpert, that they write for us; that they share our love of living, our optimism, our belief in the traditional dream of a better Australia'. The selection of writing for publication eventually caused a break between Overland and the CPA in 1958. Murray-Smith's selection policy was primarily informed by aesthetic criteria rather than the ideological criteria promoted by the CPA. Unyielding pressure from the CPA to publish ideologically informed writing forced Murray-Smith to remove the magazine from its former sponsor and proceed independently.

According to Murray-Smith, up to 4,000 copies of Overland were regularly printed in its early years, but that number dropped after the break from the CPA. The circulation dropped further in the 1960s, remaining at around 2000 for several decades. Like most editors of small magazines, Murray-Smith was faced with the challenge of attracting funds for basic publishing costs. Extra contributions from subscribers were regularly acknowledged in the 'Floating Fund' column, a tradition that continues in 2003. Early attempts to win support from the Commonwealth Literary Fund were thwarted by selection committees unsympathetic to the magazine's communist origins. But, continuing financial support from the fund was eventually won in the early 1960s.

Murray-Smith continued as editor until his death in 1988. He was succeeded by the magazine's poetry editor, Barrett Reid, who continued in the position until first John McLaren and then Ian Syson completed their editorial terms in the 1990s. Syson was succeeded in 2003 by the former associate and assistant editors, Nathan Hollier and Katherine Wilson.

Overland attracted a loyal group of poetry contributors in its first three decades. Contributors during the first decade of Overland such as Bruce Dawe, Judith Wright, Dorothy Hewett, Nancy Cato, Noel Macainsh, Chris Wallace-Crabbe and Thomas Shapcott continued to contribute poetry in the 1980s and 1990s. Later contributors include Graham Rowlands, Eric Beach, Robert Adamson, Geoff Goodfellow, Geoff Page, Laurie Duggan, Kate Lilley and Jennifer Maiden.

In both poetry and fiction Overland has shown an interest in overseas literature, particularly contemporary Chinese literature. While the contributions of poetry and fiction from this large groups of writers remained relatively strong, the value of some feature articles has occasionally been questioned by various commentators because of a perceived divergence from writing styles suitable for a general audience. At an editorial conference in 1978, Ian Turner, speaking of Overland, said, 'We have lost our popular audience; now it is rather the radical intelligentsia, say 35 years of age and older'. Echoes of this statement (not exclusively about Overland) appeared in the mid 1990s. In 1998, Duncan Richardson and Allan Gardiner complained in the pages of Overland about the trend towards academic articles unsuitable for the 'non-elite' reader, directing blame at magazines not readers for falling subscriptions.

Despite such criticism, Overland has maintained a strong reputation for investigating important social issues. Early volumes were dominated by articles on Australian literary figures and their works, but this was accompanied by articles on the bombing of Hiroshima, censorship of D. H. Lawrence's Lady Chatterley's Lover and social conditions in Aboriginal communities and Papua New Guinea. Later volumes have included essays on international conflict, immigration, multiculturalism, the practice of literary criticism, Australian historiography, sport and cinema.

Proud of its history, the newest editors of Overland, Nathan Hollier and Katherine Wilson have revisited the editorial doctrine that Murray-Smith printed in the first issue. In their first editorial they echoed Murray-Smith's call for contributions, hoping to strengthen the connection with the Australian working-class forged in the first years of Overland.