I've got 18,361 Cubs cards from 256 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1956 Topps #15 Ernie Banks The RNG gets us off to a nice start with a card of a young Mr. Cub. I did a little digging around with the action shot in the background. The players greeting him at home are #4 Ralph Kiner and #37 Gene Baker. The only time Banks hit a 3-run homer at home when Kiner and Baker scored was August 17, 1954.
1980s: 1980 TCMA All Time Cubs #7 Larry French I don't thing French would be on any listing of All Time Cubs now.
1990s: 1996 Bowman #348 Brian Stephenson Stephenson never got above AA and has a career record of 20-28.
2000s: 2002 Topps #430 Kerry Wood 2002 Kerry Wood fun fact - he led the National League in batters hit, plunking 16.
2010s: 2017 Allen & Ginter #270 Jason Heyward Heyward always seems to have a very suave, cool look.