I've got 8,002 Cubs cards (57 new Bazooka cards put me over the 8,000 mark!) 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 #364 Moe Drabowsky Moe didn't even pitch for the Cubs in 1961; he was traded to the Braves at the end of March.
1970's: Topps 1979 #663 Mike Vail Though he played in only 78 games, Vail hit well, posting a .335 average.
1980's: Team Issued 1989 #44 Steve Wilson This is what the cards looked like from Baseball Card day in 1989. It's an oversized card with an undersized photo on it. Wilson came to the Cubs in 1989 as a part of the trade that sent Rafael Palmeiro to the Rangers. He made 53 appearances and was 6-4 with a 4.20 ERA.
1990's: Conlon 1994 #1274 Bill Killefer This card was released in 1994, but the picture was taken in 1918. The photo is a rare action shot from that era. It shows Cub Bill Killefer being tagged out at home. 1918 was the veteran Killefer's first season with the Cubs. He would later spend five years as the Cub's manager.
2000's: Topps 2009 #265 Carlos Zambrano Big Z is taking a swing, something he is pretty good at (at least for a pitcher). Last year was the first time since 2002 that Zambrano didn't reach double figures in wins, going 9-7.