I've got 13,035 Cubs cards from 101 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
I've recently reached a couple milestones: The MVP, SP, and CIrca sets are now completed, pushing the number of brands over 100 and the number of cards past 13,000.
1900s - 1970s: 1960 Topps #156 Art Ceccarelli The lefty was traded to the Yankees on May 19. It seemed like he was going from the outhouse to the penthouse. Unfortunately for Art, the Yankees sent him to AAA, where he spent the next four seasons, never making it back to the major leagues.
1980s: 1989 Bowman #290 Ryne Sandberg This card comes from the first modern Bowman set, when the cards were oversized and cardboard. They snapped a shot of him in a pretty traditional baseball card pose at spring training.
1990s: 1995 Starting Lineup Sammy Sosa Sammy is taking a cut in 1994 (I'm 100% sure - the 125th patch is the indicator) at Shea Stadium (I'm about 95% sure...the orange on the side of the dugout). Sosa was one of two Cubs in 1995 Starting Lineup.
2000s: 2003 Flair #116 Felix Sanchez This is a guy that I didn't remember at all. Then I looked up his stats and found out why...He pitched in just three games for the 2003 Cubs, all in September. He gave up two runs in 1 2/3 innings. Though just 21 years old, that was the sum of his big league career. He had a stint on the DL in 2003 with a strained bicep, so I'm guessing it was arm trouble that derailed his career.
2010s: 2014 Bowman #16 Starlin Castro Castro was just one of three Cubs in the base set of Bowman this year. The picture on the card is from August 24, 2013 when the Cubs played the Padres at Petco. Castro was 1 for 4 that day, and his average dropped to just .237. It was nice to see him turn things around this year, finishing with an average of .292.