1900s - 1970s: 1976 Shakeys Pizza #36 King Kelly Though shown in a Boston uniform, I have Kelly in the Cubs sets since arguably his best playing days were when he was with Chicago. If you want to read more about the Shakeys Pizza cards, I wrote about them here.
1990s: 1995 Fleer #423 Rey Sanchez Fleer put out a pretty fancy looking base card in 1995. Sanchez was the Cubs regular second baseman in 1995 and he hit a career high in home runs. Good news right? Not really, since it only took three homers to set that new high.
2000s: 2005 Leaf #38 Aramis Ramirez This is from Leaf's final set. The angle of this picture gives you an idea of just how high the field crown was at Wrigley Field. Look at how little of the wall you can see behind Ramirez.
2010s: 2011 Topps Gold #628 Blake DeWitt I went parallel crazy in 2011, get the base, diamond, cognac, Walmart black, factory limited edition, and these golds. Having six different versions of Blake DeWitt's card is five too many!