The station began targeting St. Louis in 1983 as a Country music station WKKX a.k.a. "Kix 104 FM". However in 1994, they would switch frequencies with WKBQ and its Top 40 format (from 106.5).
In February 1997, the Top 40 format was dropped for Modern AC as "Alice 104.1" WALC. On July 15, 1998, WALC flipped to active rock and became known as "Extreme Radio 104dot1" as WXTM-FM. By the Summer of 2000, after Emmis purchased KPNT, WXTM flipped to All-80s Hits as "The Mall" (WMLL-FM), which gradually evolved to an 80s/90s hits format. That too would also go away on November 1, 2003, when the station started stunting with Christmas music until December 25, which then changed stunts to a "wheel of formats" by playing music from any given genre.
At Noon on January 8, 2004, the stunting stopped and the station flipped to an Adult Standards format as WRDA, "Red @ 104.1". The station specialized in "Music with Class" as they called it, playing classic standards singers such as Frank Sinatra and more modern 'crooners' such as Rod Stewart. After 18 months of subpar ratings and low advertising revenues, Emmis Communications sold WRDA to Radio One, for $20 million in September 2005. The station flipped to its current format on October 1, 2005 at Midnight. The first song on "Hot" was "Play" by David Banner. The call letters would change to WHHL after their slogan/motto (Where Hip Hop Lives!) to match the "Hot 104.1" handle. Radio One would take full possession of the station in 2006 after running it under an LMA (Local marketing agreement).