I've got 18,586 Cubs cards from 259 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1971 Topps #38 Jim Colborn Colborn spent most of the 1971 season in AAA. He gave up 8 runs in 10 innings for the Cubs.1980s: 1988 Fleer Traded #80 Jeff Pico Pico was a 22-year-old rookie for the Cubs in 1988. He pitched a complete game shutout in his MLB debut on May 31. After that he was a .500 pitcher over the next few seasons.
1990s: 1999 Victory #83 Gary Gaetti A late-season pickup in 1998, Gaetti hit .320 for the Cubs. The Cubs thought he could be a full time player in 1999, but the guy was 40-years-old... and it showed. He hit just .204 over 113 games.
2000s: 2006 Greats of the Game Ron Santo Fleer used a picture of a very young Ron Santo in their Greats of the Game set.
2010s: 2018 Topps Stickers #197 Jason Heyward I typically like the designs on the stickers over the flagship card set. 2018 was no exception.