In 1991, Winters earned an Emmy Award for his supporting role in "Davis Rules". In 2002, he earned an Emmy nomination as a guest star in a comedy series for "Life With Bonnie". In 1999, Winters was awarded the Mark Twain Prize for American Humor. In 2008, Winters was presented with a Pioneer TV Land Award by Robin Williams. Winters received 11 Grammy Award for Best Comedy Album nominations during his career, and won the Grammy Award for Best Spoken Comedy Album for "Crank(y) Calls" in 1996.