I've got 20,695 Cubs cards from 304 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1962 Topps #47 Bob Will In his shot Will looks more like an accountant than a ballplayer.
1980s: 1988 Topps Stickers Stickerback #11 Shawon Dunston Dunston is one player that always looks cool on his cards. He was a very photogenic player.
1990s: 1990 Donruss #223 Andre Dawson The guy had a pretty intimidating stance. Wide and lean, he was ready to mash the ball.2000s: 2004 Fleer #345 Eric Karros He didn't play for the 2004 Cubs. He became a free agent after the 2003 season and went to Oakland.