I've got 8,232 Cubs cards from 42 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950's / 1960's: Topps 1961 #382 Frank Thomas This card is special because it was my very first Cubs card. Thomas' time with the Cubs in 1961 was pretty limited. After only 15 games he was traded to the Braves. He had a pretty decent season with the Braves, hitting 25 homers and knocking in 67 runs.
1970's: Topps 1976 SSPC #308 Jim Marshall This card is from SSPC's unauthorized set. 1976 would be Marshall's last season as the Cubs skipper. The Cubs finished 75-87 for the second consecutive season. In December, 1976, Bob Kennedy was hired as the Cubs GM and he wanted his own man to lead the team. Marshall was fired and replaced by Herman Franks.
1980's: Fleer 1989 #420 Doug Dascenzo Lil' Dougie spent most of 1989 in AAA at Iowa. He did see action in 47 games with the Cubs, but hit only .165.
1990's: Stadium Club 1996 #15 Randy Myers He didn't even play for the Cubs in 1996. Despite leading the league in saves during two of his three seasons with the Cubs, they let him go as a free agent after the 1995 season. Myers was signed by the Orioles and saved 31 games for them in 1996.
2000's: Topps 2007 #126 Daryle Ward This card looks is a photoshop job. Ward wore #12 with the Braves in 2005, but switched to #32 when he joined the Cubs in 2007. On the card he's wearing #12. He came to the Cubs to add a veteran presence on the bench. He had a nice season, getting 110 at bats and hitting .327.