I've got 11,829 Cubs cards from 84 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: 1962 Topps #47 Bob Will How weird is this...just a month ago the RNG came up with Will's 1963 card and today it pulls his '62. In 1962 Will was used almost exclusively as a pinch hitter. He appeared in 87 games but only played in the field in nine of those. Most of the time it was one at bat and then back to the bench. And he wasn't too successful in the pinch either, hitting only .239.
1970s: 1979 Galasso Glossy Greats #72 Kiki Cuyler His real first name is Hazen and his middle name is Shirley....so being called Kiki wasn't so bad. And by the way it's pronounced Kai-kai...I just learned that a few years ago. I always thought it was Key-Key. The Hall of Fame outfielder spent eight of his 18 year career with the Cubs, the longest tenure of the four teams he played for.
1990s: 1997 Fleer #288 Pedro Valdes....Definitely not a world champ this time! Valdes made his big league debut with the Cubs in 1996, spending two weeks with the team in May. Fleer considered him enough of a prospect to include him in the 1997 set. The Cubs didn't agree, and Valdes spent the entire 1997 season in AAA.
2000s: 2006 Heritage Then and Now #8 Derrek Lee This is one of the few times that a Heritage card has been picked. This Then and Now card compares the NL Hits leaders, Schoendienst in 1957 and DLee in 2005. Red has 200 hits, one more than Lee did. The impressive thing about Lee's 199 hits is that almost half (99) were for extra bases.