I've got 13,964 Cubs cards from 107 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1961 Fleer #28 Jimmy Foxx I don't think anyone associates Jimmy Foxx with the Cubs. But he did spend parts of two war-year seasons ('42 and '44) in the Windy City. Why Fleer decided to show him as a Cub is puzzling?
1980s: 1986 Donruss #144 Lee Smith The 1986 season was a historic one for Smith as he became the first reliever in NL history to record three consecutive 30+ save seasons in a row.
1990s: 1993 Classic #80 Ryne Sandberg The best thing to me about this card? The uniform back with just his #23. That is a classic look. I think the Cubs uniform took a step backwards when names were added to the back on the home set.
2000s: 2007 Heritage #484 Alfonso Soriano Jim Hendry seriously overpaid to get him, but Soriano did exactly what he was signed to do in 2007....33 HRs, 70 RBIs, .299 average, and the team won the division.
2010s: 2011 Topps Top 60 Relic GS Geovany Soto This comes from a time when I was collecting all of the Cubs relics in a set. in 2011 I ended up with 18 different T60 relic cards...crazy. That was the last year I went for all the relics and instead came up with my just need one per player rule.