I've got 13,888 Cubs cards from 105 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1995 Topps #204 Ron Northey That is one weird looking C on Northey's hat. Remember, in 1952 the C on a Cubs hat was a wishbone C, shaped the same as the C on today's Cincinnati Reds hat. So why the fake C? Because Northey didn't play at all for the Cubs in 1951. The bigger question would have to be why did Topps bother making a card for a guy that was injured and didn't play the entire previous season?
1980s: 1988 Donruss #77 Ed Lynch The same question for Lynch as with Northey...why was this card even made? Lynch went 2-8 with a 5.28 ERA in 1987. His contract with the Cubs expired after the season, making him a free agent. No one picked him up and his big league career was over.
1990s: 1992 Fleer Ultra #472 Ken Patterson The lefty is one on a select group of players to play on both sides of Chicago. The Cubs picked him up for the Sox in the Sammy Sosa trade. I didn't remember that at all. In my memory, the trade was straight up Sosa for George Bell. I guess my memory failed me.
2000s: 2006 American Family #5 Mark Prior This card is from a set that I know very little about, other than that is a regular-looking Upper Deck card with an American Family Insurance logo. There is no mention of a Wrigley Field giveaway in 2006 by American Family on the schedule. There's very little mention of Mark Prior in 2006. His arm was shot, he went 1-6 with an ERA of 7.21, his brief career was over.
2010s: 2011 FInest #33 Starlin Castro Castro was one of three Cubs in the 2011 edition of Finest. The others were also young stars, Andrew Cashner and Darwin Barney.