I've got 18,615 Cubs cards from 259 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1976 Crane Rick Monday The disc has red, white, and blue, fitting since it is from the year the Monday saved the American flag at Dodger Stadium.
1980s: 1989 Star #8 Jerome Walton Star jumped right onto the Jerome Walton bandwagon and gave him an eleven-card set in 1989.
1990s: 1993 Team Issued Rolaids #2 Lee Smith This comes from a four-card set that the Cubs gave to the first 15,000 adults on Saturday, September 4.
2000s: 2006 Greats of the Game Mark Grace Game Used Bat This is my one and only Mark Grace bat card.
2010s: 2011 Topps Limited Edition Factory #628 Blake DeWitt I was all-in with the parallel sets in 2011, which means I have six different version of Blake DeWitt's card. That's probably five more than necessary for a guy like Blake DeWitt.