I've got 13,875 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: 1976 Chicago's Greats Riggs Stephenson Riggs was a .336 hitter over the course of his nine-year career with the Cubs. He was a member of two pennant-winning teams. He did well in the post-season, hitting .378 in nine World Series games. I'm guessing the rest of the team didn't follow his lead.
1980s: 1988 Topps #87 Mike Mason The lefty was released by the Cubs towards the end of spring training in 1988. The Twins picked him up and he spent the first month in Minnesota before being sent to the minors. He would never make it back to the bigs.
1990s: 1993 Topps #391 Derrick May He hit .345 during April and established himself as the Cubs starting left fielder. He ended the season hitting .295 with 10 HRs and 77 RBIs.
2000s: 2000 Stadium Club #207 Roosevelt Brown Brown spent the first and last month of the 2000 season with the Cubs and was in AAA Iowa the rest of the season. He hit .370 during the final month of the season.
2010s: 2011 Allen & Ginter Glossy #158 Marlon Byrd You can't really tell from the scan so you'll just have to trust me that this is the gimmicky glossy version. Thankfully this gimmick didn't last very long.