I've got 18,865 Cubs cards from 278 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1915 Cracker Jack #89 Lawrence Cheney After three consecutive 20-win seasons, Cheney was traded mid-season 1915 to the Dodgers. 1980s: 1987 Fleer League Leaders #39 Ryne Sandberg This card comes from a set sold only at 7-11. The boxed set has 40 cards. Though called League Leaders, it was made up of the best players from the day, not necessarily the guys who actually lead their league in any particular category.
1990s: 1998 Stadium Club #46 Jeremi Gonzalez Is it the angle of the picture or is he pitching from a really low position?
2000s: 2002 Fleer Tradition Update #199 Joe Borowski Fleer borrowed the 1934 Goudey set. Borowski was the last player to make the Cubs opening day roster and then went on to have his best season to date. Working from the bullpen, he went 4-4 with and ERA of 2.73.
2010s: 2015 Topps Stickers #215 Jorge Soler I beliver I've said this before, but more often than not I think the stickers design is better than the flagship.