I've got 14,040 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: 1961 Topps #35 Ron Santo The RNG gives me the Hall of Famer's Rookie Card just a few days after what would have been his 76th birthday.
1980s: 1985 Fleer #58 Leon Durham Looks like Fleer grabbed a shot of the Bull in Mesa, 1984.
1990s: 1993 Fleer Ultra #24 Sammy Sosa Sammy at Wrigley, the skinny pre-juice Sammy. In 1993 he became the first Cub to join the 30 HR/ 30 SB club.
2000s: 2001 Bowman #321 Ben Christensen Who?? He was the Cubs #1 draft choice in the 1999 draft but never rose above AA ball. He is more infamously known for an incident while he was in college...beaning an opposing player while the player was in the on-deck circle. The player lost sight in one eye while Christensen was suspended for the rest of the season. Yet the Cubs made him their #1 draft choice. Odd times.
2010s: 2015 Allen & Ginter #133 Addison Russell Topps was on the ball, getting Russell into the 2015 A&G set.