I've got 10,408 Cubs cards from 66 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: Topps 1957 #396 Casey Wise. This shot of Wise was taken in Philadelphia in the early part of the 1957 season, the only year the Cubs had white piping on their hats. Wise played in 43 games and hit a miniscule .179. He was traded to the Braves after the season.
1970s: Topps 1970 #429 Randy Bobb / Jim Cosman Rookie Randy Bobb was traded to the Mets at the end of spring training in exchange for catcher JC Martin. The Cubs needed a back-up catcher because Randy Hundley had injured himself during spring training and wouldn't be ready at the start of the season... I've written about Cosman before; his last name is one letter different from mine. He pitched one game for the Cubs in 1970, a one inning stint in which he gave up three runs, good enough for a 27.00 ERA.
1980s: Fleer Glossy 1989 #438 Calvin Schiraldi: Fleer put out the regular cards and a glossy version in 1989. You can't really tell the difference with the scan; you'll just have to take my word for it. Schiraldi was a lousy 3-6 for the '89 Cubs before he was sent to the Padres at the end of August.
1990s: Upper Deck 1991 #171 Hector Villanueva The catcher with the name that Harry Caray couldn't pronounce played in a career-high 71 games for the '91 Cubs. He hit .276 with 13 homers, both career-highs, too. Hector liked the home cooking as 11 of his 13 homers were hit at Wrigley.
2000s: Topps Traded 2005 #256 Kevin Collins Who?? He spent seven years in the minors, never getting out above A ball. The 2004 season was his fifth in the minors, so I'm not sure why Topps decided to include him in the 2005 set.