I've got 9,199 Cubs cards from 56 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s Topps 1952 #330 Turk Lown This is one of the high-priced high series cards from the '52 set. I've been tracking raw card sales, and since January 1, the average price for this one is $99.83. With that in mind, the picture you see is a reprint!
1970s Kelloggs 1974 #10 Billy Williams This nice looking card is from Billy's final season with the Cubs. He was 36 in 1974 and his numbers were going down. He played in a career low 117 games in '74 and hit only 16 HRs, also a career low. He also moved to first base from the outfield, playing 65 games at first and only 43 in the outfield.
1980's Topps 1988 #564 Frank Lucchesi Raise you hand if you knew that Frank Lucchesi managed the Cubs? Anyone?? I didn't think so. Lucchesi took over for the last 25 games of the 1987 season when Gene Michael was fired. The Cubs were 8-17 and for the season finished in last place. After the season GM Dallas Green resigned and was replaced by Jim Frey. Frey quickly hired his childhood friend Don Zimmer as manager and Frank Lucchesi was out.
1990s Select 1994 #32 Ryne Sandberg This card is from Select's second year, and I think its a pretty nice looking card. The card looks better than Sandberg did in 1994; he was hitting .238 when he retired in mid-June.
The card also looks better than the corncob dress that Cindy Sandberg wore at the press conference when Ryno announced his retirement. Soon afterwords, all sorts of rumors about her relationships with other players came out. It was speculated that he really retired to try and save his marriage. It didn't work; she filed for divorce ten days after he retired.
2000s Upper Deck 2001 #291 Matt Stairs The well traveled veteran spent the 2001 season with the Cubs. First base opened up because the Cubs let Mark Grace walk and super prospect Hee Seop Choi wasn't ready yet. Stairs played in 128 games, hitting .250 with 17 HRs and 61 RBIs. Late in the season the Cubs picked up Fred McGriff, leaving Stairs without a spot. He became a free agent after the season and moved on to the Brewers