* "Kup's Column": This was his daily column in the *Chicago Sun-Times*, which ran for over 40 years and was a major source of local news and gossip.
* "Kup's Show": He hosted a popular radio show on WBBM, where he continued to discuss local and national events and share his opinions.
* "Kup's Chicago": This book is a collection of his writings, anecdotes, and observations about Chicago and its people.
* "The Kupcinet Chronicles": This book delves deeper into his life and career, offering a more personal glimpse into his experiences.
While he wrote several other books, these are some of his most popular and enduring works. His writing style was unique and engaging, and his columns and broadcasts had a significant impact on Chicago culture.