I've got 21,195 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: 1970 Topps #80 Don Kessinger This is a great looking card... classic Cubs road uniform, 100th Anniversary patch, hand-written numbers inside the C on his helmet.... all good stuff!
1980s: 1989 Sportflics #15 Mark Grace Some day I'll have to go back and redo the scans of my Sportlics cards and try to capture both of the pictures on each card.
2000s: 2002 Topps #503 Tom Gordon Flash was not very good in 2002 and the Cubs traded him to the Astros in mid-August.