I've got 9,697 Cubs cards from 62 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: Topps 1959 #147 Cubs Clubbers The Cubs didn't show up in too many of the multi-player cards that Topps put out in the '50s and '60s, so this card is a bit of a rarity. This card could also be renamed "The NL MVP and a Couple Other Stiffs." In 1959 Banks hit 45 HRs, Long had 14 and Moryn added another 14 for a total of 73 homers.
1970s: Topps 1974 #598 Jim Tyrone A seventh round draft pick in 1971, Tyrone had a cup of coffee with the Cubs in 1972, but spent most of '73 in AA. He was with the Cubs for a good part of the 1974 season, but he was not very good, hitting .185 in 81 ABs. Most people don't think of this card as the Jim Tyrone card; the guy above Tyrone got most of the attention.
1980s: Donruss 1983 #477 Leon Durham The Bull had a mixed season in 1983. He made the All Star team for the second straight season, going into the break with a .310 average. But injuries to his back and thumb put him on the disabled list twice after the break and he played in only 100 games for the season.
1990s: Bowman 1997 #214 Jeff Yoder As a 20 year old in 1996, Yoder was 12-5 with the Rockford Cubbies. That impressive debut got him featured on this card. But he was injured for the entire 1997 season, and when he recovered, never got about AA ball. His last season was 2000, making only eight appearances.
2000s: Bowman 2009 BCP10 Jose Ceda Originally a Padres draft pick, Ceda came to the Cubs in a trade for Todd Walker mid-season 2006. He never rose above AA ball with the Cubs and was traded to the Marlins in November 2008. But forget about him---the big question is whose signature is on the card, because that sure doesn't look like it says "Jose Ceda"?