I've got 12,083 Cubs cards from 87 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1965 Topps #14 Len Gabrielson It was well into my adult years when I learned that Gabrielson played for the Cubs. I always thought of him as a Dodger. His time with the Cubs was relatively short, half of the 1964 season and about a third of the 1965 season. He was hitting .250 with the Cubs in 28 games when he was sent to the Giants on May 29. He went on to hit .301 in 88 games with the Giants.
1980s: 1988 Donruss #169 Jamie Moyer Such a young looking Jaime Moyer! Just think, at this point he would still have another 23 big league seasons ahead of him. In 1988, he was used primarily as a starter and went 8-15. He was sent to the Rangers after the season in the trade that brought Mitch Williams to the Cubs.
1990s: 1991 Classic Collectors Edition #104 George Bell This card is from one of four different sets put out by Classic in 1991. It looks like the picture on the card was taken in Mesa during the spring of 1991, which was the only season Bell was with the Cubs. He had a good year, hitting .285 with 25 HRs and 86 RBIs. He also made the All Star team in his one and only season in the National League. The Cubs sold high on him and traded him to the White Sox for a scrawny kid named Sammy Sosa.
2000s: 2004 Greats of the Game Forever Cubs #14 Ryne Sandberg This card comes from one of my favorite sets, Fleer's Greats of the Games. The Forever insert sets featured players from the Dodgers, Red Sox, Cubs, Mets, and Cardinals. Sandberg was one of six Cubs. The cards were numbered to the players rookie season, meaning there are 1981 of these.
2010s: 2013 Topps Commemorative Patch #40 Ernie Banks This cards comes for the Ernie Banks player collection. Notice that the cloth patch doesn't match the one in the bottom corner of the card. The cloth is a modern logo while the smaller one in the corner is from the 1960s and 1970s. How Topps to not match.