I've got 8,282 Cubs cards from 44 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950's / 1960's: Bowman 1954 #77 Bob Rush Rush was a fixture in the Cubs rotation from in the early '50's. He even made the All Star team twice, even though he was only above .500 once between 1949 and 1954. His 1954 season was typical for him, going 13-15 with a 3.77 ERA.
1970's: Topps 1976 #277 Cubs Team Floating Heads!! The second post I posted was on all of the Floating Heads. 1976 was the Cubs' centennial season. They are the only original National League team that plays in its' original city. In 1876, the Cubs won the National League's first pennant. In 1976, they didn't win much of anything. They finished in 4th place, 75-87. and manager Jim Marshall got canned after the season.
1980's: Donruss 1983 #225 Mike Proly I like the design on the 1983 Donruss cards. The bat and glove look nice. Proly was one of a host of Cubs who came from the Phillies in 1982 when Dallas Green took over. He wasn't very good in 1983, though he did get into 60 games. He was 1-5 with a 3.58 ERA. He went to spring training with the Cubs in 1984, but was released just prior to the start of the season and pitched a handful of games with the Blue Jays AAA team before his career was over.
1990's: Topps Chrome 1998 #424 Manny Alexander Alexander was the Cubs utility infielder in 1998, playing 50 games at short, 27 at second, and 19 at third. He hit .350 (9 for 25) as a pinch hitter, second best in the NL. Not a bad season.
2000's: T206 2002 #178 Joe Tinker A card from 2002 for a player that played with the Cubs over 90 years earlier. Tinker was a key member of the Cubs last championship team, the shortstop of the famed Tinkers to Evers to Chance infield combo. I'd love to see the Cubs wear these uniforms as throwback some day.