I've got 14,053 Cubs cards from 107 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1979 Topps #494 Jerry White Hey Jerry, you're posing for your baseball card. How about taking off the jacket.
1980s: 1981 Topps Coke #6 Mike Krukow This is one of eleven players in the 1981 Coke set. I guess that makes Krukow one of the top eleven players on the 1981 Cubs. The team had the worst record in the National League. Being in the top eleven was not much of an accomplishment.
1990s: 1994 Stadium Club #692 Willie Banks He was with the Cubs for just a couple years, but they were years in the height of the junk wax era. This is one of 26 Willie Banks cards from 1994 and 1995. Having those cards makes an image search for Ernie Banks cards a pain, since I label the JPEG by last name. I always have to weed out Willie while searching for Ernie.
2000s: 2006 Finest #8 Kerry Wood The 2006 season was a wasted season for Wood. He opened the season on the disabled list. Activated in mid-May, he made four starts before being shut down for the rest of the year. He wouldn't return until August of 2007. He was also done as a starter, working out of the pen for the remainder of his career.
2010s: 2014 Pro Debut #2 Chadd Krist There have been several players in the Cubs farm system that have been highly touted. Chadd Krist was not one of them. He was released by the Cubs about two months after this card came out.