I've got 19,238 Cubs cards from 285 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1955 Bowman #247 Dutch Leonard The RNG gets us off to a great start with the Bowman TV set. Leonard was the Cubs pitching coach. The signing war between Bowman and Topps left both companies short and they resorted to making cards for managers, coaches, and umpires to fill the sets.
1980s: 1988 Topps #87 Mike Mason The lefty was released by the Cubs towards the end of spring training in 1988. The Twins picked him up and he gave up eight runs in six innings, the last innings of his major league career.
1990s: 1996 Upper Deck Traded #486 Terry Adams Adams led all Cubs relievers in innings pitched so Upper Deck felt obligated to include him in the update set. Fleer did also, but Topps did not.
2000s: 2004 Bazooka #230 Sammy Sosa Is that the ball in the upper right hand corner? No home run here if that is the case.