I've got 10,979 Cubs cards from 72 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
The RNG completely ignored Topps today...don't think that has happened very often.
1950s / 1960s: 1969 Milton Bradley Ted Abernathy This card is from Milton Bradley's baseball game. I wrote about the complete set here. I'm guessing that the picture on the card is from Abernathy's time with the Braves in 1966. He was in his second go-around with the Cubs in 1969 and was the #2 man in the bullpen. He pitched in 56 games and was 4-3 with 3 saves.
1970s: 1978 Hostess #5 Bruce Sutter The RNG made a newsworthy pick with a card from the dearly departed Hostess company. The Cubs closer is posing at Candlestick Park. Sutter made the '78 Hostess set based on his break-out season in 1977. For the '78 season he had 27 saves and picked up the win in the All Star game.
1980s: 1984 Nestles #787 Bill Campbell I said that the RNG didn't pick any Topps cards today, but this one is pretty close. It's from the Nestle set, which was put out by Topps and has the same Topps designed except the Nestle name replaced the Topps name in the upper right hand corner. Soup didn't even play for the '84 Cubs...he was traded to the Phillies near the end of spring training in a multi-player swap. Bob Dernier and Gary Matthews were a couple of the players that came to the Cubs--both played major roles on the division winners.
1990s: 1992 Conlon #344 Jimmy Lavender I feel kinda funny about placing a card with an 1915 no hitter in the '90s, but since that's when the card came out, so that's where it gets placed. Jimmy Lavender had a short, six year career, and he finished 13 games under .500. But on August 31, 1915, he no-hit the Giants. He struck out eight, walked only one, and the Giants managed to hit the ball out of the infield only twice.
2000s: 2005 Donruss Elite #157 Ernie Banks This card is from my Banks player collection. It from the Turn of the Century parallel set. You can see that on 250 of these were made. Donruss gets plus points for using the older Cubs logo on the card.