The 25th anniversary issue (1997) included special retrospectives and essays examining how the magazine evolved over quarter-century of publishing. In honor of this milestone, several articles were published exploring the history and legacy of Playboy. One such article was titled "How Playboy Changed My Life," written by a man who had been a devoted reader since childhood. He described how the magazine's mix of sex, humor, and cultural commentary had influenced his worldview and shaped his values. Another article, called "The Rise and Fall of the Bunny Rabbit," traced the iconic logo's origins back to founder Hugh Hefner's early days at Esquire and the birth of Playmate of the Month. The writer noted that while the bunny has become a symbol of American pop culture, it is also emblematic of the magazine's enduring appeal as a provocative force for change. Gallery regularly celebrated milestones in similar fashion. On its tenth anniversary, for example, it commissioned artworks from some of its most famous contributors, including Andy Warhol and Salvador Dali. These were then collected into a special edition called Artists Celebrate the First Decade of Gallery, which sold out almost immediately. For the twentieth anniversary, Gallery reprinted a selection of classic works from throughout its run, including pieces by Edgar Allan Poe, H.P. Lovecraft, and Ray Bradbury. In addition to these retrospective issues, special commemorative editions often included interviews with notable figures associated with Gallery or essays on its impact on literature and popular culture.
For example, the 30th anniversary issue (2017) featured an interview with Stephen King about his work with the magazine. The author discussed how his relationship with Gallery began when he was first approached about writing a story for its horror section in 1984 and continued through the years, leading to him becoming one of their most prolific contributors. Another article examined Gallery 's influence on sci-fi and fantasy fiction by exploring the careers of authors such as George R.R. Martin and Neil Gaiman who got their start in the pages of the magazine. While Gallery did not always receive positive press over the years, it remains an important part of American publishing history. As this article illustrates, its legacy is one that continues to be celebrated and debated today.