Many coins of the classic era of United States ("US") commemorative coins depict important historical figures, but how many of these figures ever served as a Mayor of a City/Town? Let's find out!
1921 Alabama Statehood CentennialThe obverse of the Alabama Statehood Centennial coin presents the conjoined portraits of William Bibb and George Kilby - the first and then-current Alabama Governor, respectively. Kilby was the Mayor of Anniston, Alabama from 1905 to 1909; Bibb was never a Mayor.
1921 Alabama Statehood Centennial Half Dollar
1925 Fort Vancouver CentennialThe obverse of the 1925 Fort Vancouver Centennial Half Dollar features a left-facing portrait of Dr. John McLoughlin. He served as the Mayor of Oregon City in 1851 - this was after he retired from the Hudson's Bay Company as its Chief Factor of its Columbia District; he managed Fort Vancouver from 1824 to 1845.
1925 Fort Vancouver Centennial Half Dollar
1926 American Independence SesquicentennialThe conjoined portraits of George Washington (First US President) and Calvin Coolidge (then-current US President) are presented on the obverse of the 1926 American Independence Sesquicentennial Half Dollar. Coolidge was the Mayor of Northampton, Massachusetts. He served two terms between January 3, 1910 and January 1, 1912, before becoming the 30th US President in 1923.
1926 American Independence Sesquicentennial Half Dollar
1936 Albany Charter 250th AnniversaryThe 1936 Albany Charter 250th Anniversary Half Dollar is a twofer special!
The coin's reverse depicts (at left) Thomas Dongan, the Governor of the Province of New York in 1686; it was Dongan who signed the Albany Charter. To the right are seen two men: Peter Schuyler, the Head of the Commissioners for Indian Affairs in the area (he is depicted holding the Charter); and Robert Livingston, who was the Secretary for Indian Affairs.
Schuyler and Livingston would each go on to serve as the Mayor of Albany. Schuyler was Albany's first mayor (he served from July 1686 to October 1694); Livingston served from 1710 to 1719.
1936 Albany Charter 250th Anniversary Half Dollar

Did I forget anyone?
For other of my posts about commemorative coins and medals, including more Quick Bits stories and others about each of the coins referenced here, see:
Commems Collection