I've got 10,017 Cubs cards from 64 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s Bowman 1951 #211 Hal Jeffcoat He had a decent season in 1951, hitting .273 in 113 games. He didn't have any power to speak of, with only four homers, and knocked in only 27 runs. But it is a really nice looking card.
1970s MSA 1976 Jose Cardenal It wasn't too long ago that I had a post with the entire Cubs set of five players from this 1976 set. The 1976 season was Jose's last as a full-time player. But he was already in decline, as his average dropped 18 points and he had 21 fewer RBIs. But you can see that his fro was still growing strong.
1980s Topps 1980 #381 Cubs Team The random number generator gives us some floating heads! Too bad it was of a really bad team. Preston Gomez is the manager on the card, and 1980 was his first as Cubs skipper. But he didn't last very long, only 90 games. The team was 38-52 when he got the boot. Replacement manager actually did worse, as Joey Amalfitano's tenure saw the team post a 26-46 record. For the year, that was 64-98 and last place.
1990s Bowman 1998 #423 Courtney Duncan The Cubs took Duncan in the 20th round of the 1996 draft. He spent the 1998 season with AA West Tennessee. The Cubs were grooming him as a starter, and all of his 1998 appearances were as a starter. With 29 starts, he was 7-9 with a 4.26 ERA. He did eventually make it to the Cubs in 2001 and 2002, but didn't do anything too impressive and the Cubs let him go after the 2002 season.
2000s Upper Deck 2009 #64 Kerry Wood This card is from the first series of Upper Deck's 2009 set, and is Wood's last UD card as a Cub. He spent the 2009 season with the Indians, who had signed him as a free agent after the 2008 season. UD did have a card of Wood with the Indians in the second series.