I've got 12,397 Cubs cards from 88 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1963 Topps Peel Off Ernie Banks These stickers were inserts in the 1963 set. Back then the inserts weren't what you chased, the base cards were. These were just seen as a nice little bonus. Since most kids peeled the stickers off and stuck them some where, these are a bit harder to find that other inserts from the '60s.
1980s: 1985 Fleer #58 George Frazier He was a part of the trade that brought Rick Sutcliffe to the Cubs in June, 1984. That deal is known as the Rick Sutcliffe trade, not the George Frazier trade. In 1985, working out of the bullpen, Frazier was 7-8 win an ERA of 6.39.
1990s: 1992 Leaf #381 Danny Jackson The Cubs signed Danny Jackson to a big bucks contract before the 1991 season. He lasted only a year and a half in Chicago was was a big bust. He started 19 games for the '92 Cubs was and was 4-9 before being traded to the Pirates.
2000s: 2005 Topps Total #227 Corey Patterson The 2005 season was Corey's last as a Cub. As he lost his patience at the plate, the team lost patience with him. For the year he hit only .215. He had 97 hits but struck out 118 times. The Cubs traded KKKKorey after the season.
2010s:2011 Topps Manufactured Glove #RH Rogers Hornsby This is one of five Cubs that had these fake glove patch cards. There was also a numbered black version of the glove. I ended up with all ten of the Cubs cards. It was also the last time I chased after all the Cubs when Topps made these manufactured type cards.