I've got 11,940 Cubs cards from 86 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: 1958 Topps #91 Chuck Tanner This card gives a good look at the Cubs 1957 road uniforms which had the full team name on them. This was the only season they wore these; in 1958 they went back to road unis with just "Chicago" on them. You can also see a bit of the white piping on the hats which was also a '57 only feature.
1970s: 1971 Topps #726 Paul Popovich The 1971 season saw Popovich play in the most games (89) since 1968. He had a career high in RBIs.....28...which doesn't seem very high at all. Four of the RBIs game in one blow, his first career grand slam, which he hit on September 11 off of Jerry Reuss of the Cardinals.
1980s: 1989 Topps #613 Gary Varsho The Cubs had high hopes for Varsho in 1989 after he led the National League in pinch hitting in 1988, going .393 in the pinch. He appeared in 61 games for the '89 Cubs, but started only eleven of them. He wasn't able to match his pinch hitting prowess from the previous year, though, hitting only .138....not very clutch. With the emergence of Jerome Walton and Dwight Smith in the outfield, Varsho spent part of the season back in AAA.
1990s: 1998 Topps Devil Rays #437 Rod Beck This card is from the Devil Rays Inaugural Season set. The set's special logo is on Beck's legs. The Shooter was the Cubs closer in 1998 and had a really nice season. He led all National League pitchers in both games and games finished and was second in saves with 51.
2000s: 2006 Turkey Red #604 Sean Marshall The lefty broke in with the Cubs in 2006 and Topps thought enough of him to include him in the Turkey Red set. Marshall was used exclusively as a starter in the 2006 season. In 24 games, he was 6-9 with and ERA of 5.59.