I've got 20,692 Cubs cards from 304 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1970 Kelloggs #50 Ernie Banks This card has me so conflicted. On one hand you have a smiling Mr. Cub in the home pinstripes. On the other hand, he is at Shea Stadium.
1980s: 1982 Topps #62 Mike Tyson Before there was the powerful and crazy boxer, there was the second baseman. As opposed to the hard hitting boxer, the infielder was pretty light-hitting. After hitting just .185 for the 1981 Cubs, he was released towards the end of spring training in 1982, ending his 10-year career.
1990s: 1994 Triple Play #75 Mike Morgan The Cubs were one of eleven big-league stops for Morgan. I didn't realize it until I started working on this, but he played more years with the Cubs than with any of the other ten teams. The 1994 season was his worst. A 2-10 record with an ERA of 6.69 is pretty bad. Good thing for him the season was cut short by the strike. He had three different stints on the DL, but obviously never got healthy.
2000s: 2008 Heritage #580 Kosuke Fukudome Remember when he was all the rage? He had cards and inserts in just about everything in 2008.
2010s: 2010 Topps Update #85 Andre Dawson This card is a short print variation. Starlin Castro is the real #85 in the set, but the Hawk got an SP card.