This article discusses a little-known meeting in 1889 between Oscar Wilde and Arthur Conan Doyle, facilitated by a magazine editor, which led to commissions for The Picture of Dorian Gray and The Sign of Four. While seemingly an unlikely pairing, the article argues that their works share surprising similarities, particularly exploring the fin-de-siècle aesthetic and hinting at a queer subtext in Doyle’s early work, “John Barrington Cowles,” which predates his Sherlock Holmes stories. The article points to shared themes like addiction and artistic interests in both authors’ writing, suggesting a deeper connection than previously recognized.