I've got 11,147 Cubs cards from 77 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: 1959 Topps #414 Dale Long Long is posing in front of the screen at San Francisco's Seal Stadium. He was a part-time first baseman for the Cubs and at 33, his skills were starting to decline. His batting average dropped 35 points over the previous season and his homers and RBIs fell too.
1970s: 1976 Topps #126 Tom Dettore You'd have to be a pretty hard-core Cubs fan to recognize the name Tom Dettore. The Cubs picked him up in April, 1974, from the Pirates. He spent the next two seasons bouncing between AAA and Chicago. He was a spot starter/reliever and his numbers were unspectacular. In 1975 he pitched in 36 games and put up an ERA of 5.38. He made the '76 Cubs out of spring training but was had an ERA of over 10 in four April games and was released on April 22. He was picked up by the Padres and spent the rest of 1976 in AAA.
1980s: 1980 TCMA All Time Cubs #9 Billy Herman This is one of those confusion cards....released in 1980, but of a player that played in the 30's and 40's. The card comes from TCMA's All Time Cubs set issued in 1980. This was the third year in a row that TCMA put out an All Time Cubs set, and each of the years the sets included the same players. The 1980 set is probably the best looking of the three. Herman's cards from the '78 and '79 sets look....
1990s: 1997 Score #259 Tyler Houston The 1997 season was Houston's first full season with the Cubs, having come over in a trade from the Braves in June, 1996. He had a pretty nondescript year, hitting .260 with 2 homers and 28 RBIs in 72 games.
2000s: 2007 Heritage #184 Rich Hill This card comes from Hill's career-peak season, He started 32 games for the Cubs and was 11-8 with a 3.92 ERA. He also struck out 183 hitters in 195 innings, a pretty decent ratio. He lost his control the next year and spent most of 2008 in the minors trying to right the ship.