I've got 9,521 Cubs cards from 60 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: 1969 Topps Deckle Edge #18 Don Kessinger The Deckle Edge cards are among my favorite inserts. The funky edge, the glossy card, the blue autograph--all great features. It's interesting to me that Topps included Kessinger (Ron Santo was the other Cub in the set), but left out bigger names like Banks, Williams, and Jenkins.
1970s: 1979 Hostess #27 Bill Buckner The randomizer picked one of my all-time favorites! This Hostess card highlights the hairyness that is Bill Buckner. We've got the mustache, unibrow, and even some neck hair. In Genesis 27:11, Jacob says that his brother Esau is a hairy man, but he is a smooth man. Bill Buckner = Esau.
1980s: 1985 Topps #384 Jody Davis Jo-Dee! Jo-Dee! Fan favorite Jody Davis was at the height of his popularity in 1985. The previous season he was an All Star and was 10th in MVP balloting. Unfortunately his numbers fell off in 1985, as he had 36 fewer RBIs and his average dropped 24 points. The rigors of being an everyday catcher had starter to take a toll.
1990s: 1994 Collectors Choice #28 Brooks Kieschnick This is one of 34 different Brooks Kieschnick cards in my collection. That's a lot of cards for a guy who played in only 64 games for the Cubs over two seasons. He was a bust for the Cubs but did gain some notoriety when he was both an outfielder and pitcher for the Brewers in 2003 and 2004.
2000s: 2009 Upper Deck #567 Sean Marshall Topps hasn't seen fit to include Marshall in many base sets but at least Upper Deck did in 2009. In fact, in a six season career with 292 game appearances, Marshall has made the Topps base set only once. Boo Topps! Upper Deck had him in the base set five times, from 2006 - 2010.