I've got 12,370 Cubs cards from 88 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1967 Topps #578 John Boccabella When this card game out, he was still John Boccabella. It would be two more years before he would become John Boccc-a- belll-aaaa! In 1967, he was just one of a parade of rookies that Leo Durocher put out each year as the player to replace Ernie Banks. Boccabella did not replace Mr. Cub.
1980s: 1985 Donruss #67 Ryne Sandberg This is the card Donruss issued for the reigning NL MVP. Sandberg has a decent season in 1985, hitting .305 with 26 HRs and 83 RBIs. He also won his third straight Gold Glove.
1990s: 1997 Pacific #258 Scott Servais The Cubs starting catcher in 1997, he put together a serviceable season. In 122 games, he hit .260 with 6 HRs and 45 RBIs.
2000s: 2005 Topps Factory Set Bonus #5 Brandon Sing This card was one of five bonus cards that were included in the Cubs version of the complete set Topps factory set. Sing has 32 homers in high A ball in 2004 which was enough to grab the attention of the Topps people. He hit 26 for the Cubs AA team in 2005, but after splitting the 2006 season between AA and AAA, the Cubs released him.
2010s: 2012 Heritage #113 Kerry Wood On his final Heritage card, Kerry Wood has a rather stern look. Maybe he knew his career was just about finished. He pitched in just 10 games in 2012 and wasn't good at all, He retired on May 18 after striking out the final batter he faced, White Sox outfielder Dayan Viciedo.