I've got 13,651 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: 1965 Topps #596 Don Landrum The 1965 season was the only one in his eight year career that saw Landrum as a full-time player. He played in 131 games for the Cubs. The results weren't good... a .226 average, 6 HRs, 34 RBIs. After the season he was traded to the Giants in a steal of a trade for the Cubs. Landrum and pitcher Lindy McDaniels went to the bay and the Cubs got Bill Hands and Randy Hundley. The trade was headline news when it was made,
1980s: 1984 Fleer #494 Fergie Jenkins This is a sad card, as was any 1984 card of Fergie. The Cubs released him during spring training of 1984 and that ended his Hall of Fame career. Here is the Tribune article the day after he was let go.
1990s: 1990 Upper Deck #736 Derrick May May made his major league debut for the Cubs in 1990. He played in 17 games after getting a September call-up. He hit .246 in 17 games.
2000s: 2001 Topps Chrome #317 Sammy Sosa Sammy and his needle were still at the to of their game in 2001. He became the first player in MLB history to have three seasons with 60+ home runs. He hit .328 and knocked in 160 runs. All that wasn't enough to win the MVP, though, as he finished second to Barry Bonds and his needle.
2010s: 2014 Topps Update #14 Justin Grimm The righty has a nice year for the 2014 Cubs out of the bullpen. He made 73 appearances and posted a 5-2 record.