I've got 21,289 Cubs cards from 316 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1975 Pioneers of Baseball #17 Johnny Evers Yes, I have this in my collection even though it shows Evers in a Braves uniform. I'm assuming I used some team set listing when I bought the cards from the set that had him with the Cubs.
1980s: 1983 All-Star Game Program Larry Bowa These cards come from the game program, which was printed far in advance of the game. Therefore, they made cards of all the nominated players, not the players on the actual teams. Bowa was definitely not on the NL All-Star team in 1983.
1990s: 1990 K Mart #2 Ryne Sandberg This comes from the last of three sets that Topps produced for K Mart.
2000s: 2007 Sweet Spot Signatures #SD Shawon Dunston Dunston never had a certified autograph during his playing time, so this isn't a rule follower for me. Instead, I picked it up because I wanted an autograph card for him and this one looked pretty nice.
2010s: 2012 Bowman #55 Geovany Soto Boy, that ball looks like it went straight up.