I've got 8,877 Cubs cards from 51 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: Topps 1960 #412 Bob Anderson Bob was the #2 starter for the 1960 Cubs, going 9-11 with a 4.11 ERA. Not a great record, but I like the card, with the Wrigley scoreboard in the background. And Bob sure looks like a happy guy.
1970s: Topps 1974 #603 Rookie Catchers Tom Lundstedt Lundstedt is a Chicago area boy, growing up in Arlington Heights and attending the same high school, Prospect, as Mike Quade and Dave Kingman. A first round draft pick in 1970, he never lived up to the hype. He played in 22 games with the Cubs in 1974, batting an anemic .094. After the season he was traded to the Twins for Mike Adams.
1980s: Donruss 1981 #558 Barry Foote We actually get two Barry Foote cards in a row since he was also on the Lundstedt rookie card. Foote spent very little time with the 1981 Cubs. After going hitless in nine games (26 plate appearances) he was traded to the Yankees. I wonder how often a guy with a .000 average gets traded? You have to give GM Bob Kennedy credit for finding a team willing to take Foote. He did get some hits with New York, raising he season average to .177. He even made the Yankees post-season roster and appeared in the NL playoffs and the World Series.
1990s: Star Nova 1990 #140 Ryne Sandberg Ryno had a great year in 1990, one of the best ever for any second baseman. He led the NL in homers with 40 and won his eighth straight gold glove.
2000s: Donruss 2005 #140 Todd Walker Walker's 2005 season got off to a bad start because of a knee injury he got when Carlos Lee banged into him while turning a double play. He was on the DL from April 11 to May 25. He finished the year appearing in 110 games and hit .305 with 12 HRs and 40 RBIs.