I've got 9,991 Cubs cards from 64 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s Topps 1951 #14 Wayne Terwilliger The random number generator came up with a really low number, and got me a card from Topps' first set. This card is from the red back set. Terwilliger spent less than half the '51 season with the Cubs. In 50 games he hit .214 with no homers and only 10 RBIs. On June 15 he was sent to the Dodgers in a eight player swap. Can you imagine that today; two teams swapping four players each in June.
1970s: Kelloggs 1975 #29 Jose Cardenal It's a big 3-D afro! I'm not sure what that is in the background. Are those blurred-out grandstand seats? The 1975 season was probably Jose's peak. He hit .317 and showed decent power for a little guy, with 12 homers. He also drove in 77 runs, a career best. He even stole 34 bases, which was good for fifth in the league.
1980s: Donruss 1986 #438 Steve Engel I'm a die hard Cubs fan and even I had to scratch my head and say "Who??" when the random number generator came up with this one! So I looked up his stats and now I know why I forgot about him. He pitched for the Cubs in only one season, 1985. In 11 games he was 1-5 with a 5.57 ERA. Pretty forgettable stats! He spent all of the 1986 season AAA, with Iowa and later Tucson, when the Cubs traded him to Houston. He bounced around the minors through the 1988 season.
1990s: Upper Deck 1992 #714 Diamond Skills Shawon Dunston. The Cubs shortstop got the nod for best infield arm. Anyone who saw him play would have a hard time not agreeing. The guy had a cannon. He wasn't always accurate (Mark Grace saved him many an error), but the man could sling a ball. On the card it looks like he's making a throw on a cold spring day at Wrigley.
2000s Stadium Club 2008 #74 Rich Harden. Topps put this set out after giving Stadium Club a three year rest. It didn't catch on and hasn't been heard from since. The Cubs picked Harden up midseason in 2008 and he was very good, when he wasn't hurt. He went 5-1 with a 1.77 ERA. Since then he's been fragile and only a 500 pitcher. And I really mean, a .500 pitcher: 2009 9-9, 2010 5-5, 2011 4-4. It doesn't get any more 500 than that!