Imagine Radio was a trailblazing Internet radio service that captured the zeitgeist of late-90s digital music innovation. Launched in 1998 and gaining wider attention in 1999, Imagine Radio allowed listeners to tune in to 20 pre-programmed stations or, with a then-groundbreaking level of personalization, create custom online stations by selecting and rating their favorite artists. While users couldn’t pick specific songs due to legal constraints, the system cleverly adjusted playlists to play preferred artists more often, offering a uniquely tailored listening experience. Streaming in RealAudio and Windows Media Player formats, Imagine Radio paved the way for today’s custom music services. Its influence grew when Viacom acquired the platform in early 1999 and integrated it into MTV’s digital presence, but the original site was soon shuttered, making Imagine Radio a bittersweet icon of the early days of online music discovery.