I've got 13,741 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: 1973 Kelloggs #54 Ron Santo In 1973 Kelloggs ditched the 3D format and went to plain cardboard. Luckily, they returned to 3D the next year. This card shows Santo in the 1972 road uniform.
1980s: 1987 Fleer Glossy #562 Leon Durham The 1987 season was the Bull's last full year with the Cubs. He hit a career high 27 homers, the most by a Cubs first baseman since Jim Hickman hit 32 in 1970.
1990s:1990 Star #1 Ryne Sandberg This card is the first of nine Sandberg cards from the 1990 Star base set. Ryno's looks pretty intense. He had a career year in 1990, hitting 40 homers and winning Gold Glove #8. He became the first player in MLB history to have a 40 homer run season (1990) and a 50 steal season (1985). He was the NL's leading All Star game vote-getter.
2000s: 2002 Fleer #122 Augie Ojeda Little Augie is turning a double play against the Pirates at Wrigley. The game--July 25, 2001. Abraham Nunez led off the game with a single, but the next hitter, Warren Morris, hit into a 4-6-3 double play. The Cubs would go on to win the game 6-5.
2010s: 2103 Team Issued Season Tickets #28 Greg Maddux This card is from a Cubs/Topps set given to the 2013 season ticket holders. It is from game #28 on May 31. Maddux was chosen for the card because he's #31 on the 31st. The Cubs beat the Diamondback that day 7-2. It was their fifth win in a row, the longest win streak they would have in 2013.