Answers revealed in the comments.
In the 1990s, every show that won the Primetime Emmy Award for Outstanding Comedy Series had a title character, except for one. Name that show, which won in the first half of the decade, giving it its fourth and final win in the category.
Two 20th century U.S. presidents had previously served as Cabinet Secretaries – one as Secretary of War beginning in 1904 and one as Secretary of Commerce beginning in 1921. Name either of those presidents.