I've got 18,521 Cubs cards from 257 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1956 Topps #179 Harry Chiti We can assume the picture on this 1956 card was taken in 1955. Chiti was 22 years old during the 1955 season. He looks much older than 22.
1980s: 1985 Team-Issued Ray Fontenot When the Cubs entire starting rotation spent time on the DL in 1985, Fontenot was one of the guys who picked up the slack. He was not very helpful, going 6-10 for the year.
1990s: 1997 Bowman's Best #16 Mark Grace Does anyone know what that is supposed to be in the upper left background?
2000s: 2003 Fleer Traded #26 Kenny Lofton Lofton was a great mid-season pickup and was great at the top of the lineup.