During the late teens and the twenties, "college life" came to be identified with the image of the fraternity man, the raccoon coat, a certain jazz age sophistication, and above all, by a fierce loyalty to alma mater's football team. Much of that sensibility is reflected in the finest program cover art from the period - not surprisingly, since most of the covers were produced by students who also contributed artwork to campus humor and literary magazines.

Clayton Seagears, LS&A '23, devoted most of his artistic talents to the campus humor magazine the Gargoyle, but found time to do the 1920 Chicago game cover. Bryan Warman, a trumpet player in the Marching Band and on the art staff of Chimes and the Michignensian was responsible for the 1921 Minnesota cover. The covers for all the 1922 programs appear to be the work of James C. House, yet another Chimes artist. Possibly the most prolific student artist was Alvin Wolfson (Law '25) who created covers for at least six programs between 1924 and 1926, including the 1923 Minnesota and 1924 Iowa games. The 1924 Northwestern program cover was the work of T.A. Elbert Vyse, an editor of the Gargoyle and two-time golf letterman.

Between 1916 and 1924, the official game programs were published by the Board in Control of Student Publications. When the Athletic Department hired Philip C. Pack as its first director of publicity in 1924, the production of game programs was taken over by the department. The uncredited artist of the 1925 Ohio State program nicely captures the feeling of a Jazz Age football Saturday at the gates of Michigan's Ferry Field. Likewise, the 1926 Wisconsin cover embodies the spirit of the ever-loyal alum. Both the 1926 Wisconsin and Illinois covers are uncredited, but appear to be the work of the same artist. The other three 1926 programs were done by Alvin Wolfson, one a portrait of coach and Athletic Director Fielding Yost.

An artist identified only by the stylized monogram AB produced original paintings for three of the 1927 covers. A dramatic action painting, hinting at things to come, graced the program cover when Ohio Wesleyan played the first game at Michigan Stadium. The 1927 homecoming program featured captain and three-time All-American Bennie Oosterbaan. The Bentley's copy was autographed by Fielding Yost himself, apparently at a reception in Muskegon - Oosterbaan's hometown.

The 1929 programs were the first (and as far as can be determined the only) covers to tap the talents of the faculty. The high-stepping drum major on the 1929 MSC program is the work of J.T. Bittenger, a graduate student and instructor in the College of Art and Architecture. Harvard made its only visit to Ann Arbor in 1929. The stark, compelling graphic created for the game program by professor of architecture William C. Titcombe was unlike any previous cover.