I've got 13,847 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: 1971 Fleer World Series #5 1907 With the World Series in progress, the RNG gives us a card from one of the two Cubs championship seasons.
1980s: 1980 Topps #594 Dick Tidrow Dirt was Bruce Sutter's setup man in 1980. He made a team-record 84 appearances and was 6-5 with a 2.79 ERA.
1990s: 1995 Leaf #151 Randy Myers The lefty was the ace of the bullpen for the 1995 Cubs. He had a league-leading 38 saves, the second time in three years that he led the NL. For reasons I never understood, the Cubs didn't bother to try to re-sign him after the season. Instead he went to the Orioles, who got him for $1.5 million less than what the Cubs paid him in '95.
2000s: 2004 SP Authentics #18 Sammy Sosa Oh the irony of Shammy in a set called Authentics.
2010s: 2013 Topps Stickers #189 Carlos Marmol Marmol is excited because he walked just one batter in this appearance. It was a rare event. He walked at least one hitter in more than half of his games with the Cubs that season. The team finally gave up on him and shipped him to the Dodgers in July.