I've got 13,885 Cubs cards from 105 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1955 Bowman #224 Dee Fondy I love the '55 Bowman TV set cards. They've got Fondy posing at Shibe Park in Philadelphia. The Cubs first baseman had a decent 1955 season, hitting .265 with 17 HRs and 65 RBIs.
1980s: 1985 Topps Stickers #35 Rick Sutcliffe The sticker says "Peel Here." I did not peel.
1990s: 1995 Topps #330 Randy Myers This is the second 1995 Myers card selected by the RNG over the past couple weeks. That's two more appearances than he had for the 1995 Cubs. He had become a free agent after the '94 season and went to the Orioles.
2000s: 2002 Opening Day #96 Jon Lieber Here's one from the era when Opening Day cards were colored differently than the base set. After winning 20 games for the Cubs in 2001, Lieber was hurt in 2002, starting just 21 games and posting a record of 6-8.
2010s: 2012 Heritage Clubhouse Collection #MG Matt Garza I wish more of the jersey's pinstripe was visible. All that is seen is a sliver on the bottom right side.