I've got 12,811 Cubs cards from 97 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1961 Topps #196 Ed Bouchee Wow, the RNG picked a card and player that I've written about a few times. Click here for a post about how I personally knew Ed. And here I wrote about picking up an autographed version of the 1961 card.
1980s: 1986 Topps #384 Steve Trout You don't see many card today that show the player without a hat. This one would be perfect for Panini--no hat and the jacket covers up any logos on the jersey. Trout's career was on the decline in 1986 and he was used as both a starter and reliever. He wasn't very good as either, finishing the year 5-7 with an ERA of 4.75.
1990s: 1993 Bowman #200 Ryne Sandberg Ryno seems to be looking up into the Arizona sky--wonder why he didn't flip his glasses down. Do any players use the flip down sunglasses anymore?
2000s: 2000 Topps Chrome #106 Mickey Morandini Mickey was with three teams during 2000; none of them the Cubs. He signed as a free agent with the Expos, but they sold him to the Phillies at the end of spring training. In early August the Phillies shipped him to the Blue Jays.
2010s: 2010 Finest #8 Derrek Lee This was one of D-Lee's last cards as a Cub. He was traded to the Braves in early August for three prospects that never panned out.