I've got 15,291 Cubs cards from 128 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1979 Diamond Greats #106 Hy Vandenberg Makes you wonder how a guy with a career record of 14-10 and an ERA of 4.32 is considered a Diamond Great.
1980s: 1989 Donruss #513 Jeff Pico The 1989 season was the best of the three years he spent in the major leagues. Working almost exclusively out of the bullpen, he was 3-1 with an ERA of 3.77.
1990s: 1991 Donruss #374 Greg Maddux He led the league in both starts and innings pitched in 1991. His record was 15-11, which wasn't too bad for a team with just 77 wins.
2000s: 2006 SP Legendary Cuts Baseball Chronology Platinum #BW Billy Williams It is very fitting that the man with the sweet swing is in a set called Legendary Cuts (though I don't think the brand name refers to taking a swing).
2010s: 2012 Historical Stitches #AD Andre Dawson If Topps had a more perverse sense of humor, they would have used this picture on the card...