I've got 13,963 Cubs cards from 107 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1957 Topps #16 Walt Moryn Moose had a good year in 1957. He was second on the team in games played and RBIs and also belted 19 homers
1980s: 1987 Topps Stickers #61 Ryne Sandberg Looks like Topps caught Ryno at spring training.
1990s: 1994 Score #370 Jose Vizcaino What an odd looking position they caught him in. Is he heading to a base, ducking out of the way, taking off from first?
2000s: 2004 Heritage #138 Mark Grudzielanek This card's portrait picture seems to have captured him deep in thought. Is he thinking, "How could we have blown a 3-1 lead to the Marlins in the NLCS?"
2010s: 2013 Topps #299 Darwin Barney The RNG picked my guy! Darwin is celebrating a walk-off home run against the Padres on May 30, 2012.