Lileks's first foray into radio came in 1987, while he was a writer with "City Pages". He became a regular guest on the Geoff Charles show, an afternoon talk show on KSTP. When Charles left the Twin Cities, Lileks filled the slot and served as an afternoon-drive host on KSTP for a time in the late 1980s. In the mid-1990s, after returning from Washington DC, Lileks reappeared on KSTP with a new program, "The Diner" – a show set in a fictional 1950s-era diner.