I've got 16,197 Cubs cards from 135 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1955 Bowman #137 Bob Talbot Talbot played in 114 games in 1954, which was good enough to get a card in the 1955 Bowman set. Yet after 1954 he never played in the major leagues. He knocked around in the minors until 1960.
1980s: 1982 Fleer #603 Lee Smith This is one of Smith's first cards. Fleer, Donruss, and Topps all made a card for him for the first time in 1982.
1990s: 1990 Baseball Wit #19 Ernie Banks This card uses a nice-look mid-Sixties picture of Mr. Cub at Shea.
2000s: 2006 Upper Deck #103 Ryan Dempster Dempster was always someone who appreciated the fans.
2010s: 2013 Topps Cut to the Chase #34 Ernie Banks These die cut cards from 2013 were awesome. Too bad they don't make them any more.
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