I've got 13,736 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: 1976 TCMA 1938 Cubs Clay Bryant That picture looks more like a Hollywood headshot than a team publicity photo. So the Cubs had a Bryant on a pennant-winning team. I sure hope history repeats itself soon!
1980s: 1988 K Mart #30 Rick Sutcliffe This K Mart set from 1988 highlights memorable moments of the Eighties. Sutcliffe's moment was his 14 straight wins during the 1984 season. The guy was pretty amazing for the Cubs, going 16-1 and leading the team to the NL East crown.
1990s: 1994 Donruss #61 Shawn Boskie Boskie's time with the 1994 Cubs was pretty short. After making just two appearances, he was traded to the Phillies for Kevin Foster on April 12. He was 4-6 with the Phillies over the rest of the season.
2000s: 2004 Topps Factory Set Bonus #4 David Kelton This is the second week in a row that the RNG gives us a bonus card from a Cubs factory complete set. Kelton spent a few week in May and June on the Cubs roster and had just one hit. He stuck around in the minors through the 2006 season.
2010s: 2011 Finest Rookie Autograph/Relics #87 Andrew Casher This comes from my autograph and relics collection...kills two birds with one stone. Rizzo for Cashner -- the Cubs got the better of that deal.