While not politically oriented in the style of strips such as Garry Trudeau's Doonesbury, the strip often pokes fun at various social and political issues of the day, especially when Belfry makes an appearance.
The strip won MacNelly the Reuben Award for the year 1979.
|P. Martin "Shoe" Shoemaker||purple martin||The cigar-smoking editor (patterned after Jim Shumaker whom MacNelly worked for at the Chapel Hill (NC) Weekly) of The Treetops Tattler-Tribune, whose difficulties with his various ex-wives is legendary. He is the boss of Cosmo & Loon with a very similar management style to Mr. Dithers in the comic series Blondie.|
|Prof. Cosmo Fishhawk||osprey||The overeducated but underachieving osprey columnist whose computer expertise is almost as poor as his understanding of women. His trademark desk is always overflowing with a very tall stack of papers, extending beyond the frame. Although the title of the strip is Shoe, Cosmo is arguably the main character, as the majority of the strips revolve around his life.|
|Roz||unknown||Waitress at, and/or likely owner of, the local diner (Roz's Roost) where many of the characters gather|
|Skyler||skylark||An overeducated but underachieving nephew whom Cosmo is raising. In 1986, Skyler accepted what he mistakenly believed to be a summer job with the "United States Marine Corporation", soon finding himself at Marine Corps Recruit Depot Parris Island for the summer, during which time his descriptions of events in his letters home to Uncle Cosmo composed a predominance of the strips. Skyler's correspondence took a front seat again in the summer of 1987 while he completed advanced training, and in the summer of 1988 when he went to sea.|
|Sen. Batson D. Belfry||A beltway blowhard, seemingly patterned after Tip O'Neill and Ted Kennedy, and whose name is a pun of "bats in the belfry"|
|Irving "Irv" Seagull||gull||A local repairman.|
|Loon||loon||A mail and newspaper carrier whose aeronautic skills are the subject of recurring jokes, based on former Vietnam POW Navy Pilot Paul Galanti|
|Wiz||merlin||The "Merlin of motherboards," he appears as a wizard in a pointed hat and star-covered robe, carrying a magic wand. He is often called in by The Professor to fix his office computer. ("Okay, first, let's get your fist out of the computer screen.")|