I've got 12,342 Cubs cards from 88 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1960 Fleer #43 Paul Derringer This card is one of those "should I or shouldn't I" cards. The 1960 Fleer set doesn't list teams, so when I put my set together I used the checklist from Teamsets4U. The hat does have a C on it, but it looks more like he's wearing a Cincinnati Reds uniform. Derringer spent time with both teams, but far more time was spent with the Reds. Should I keep it with the rest of my Cubs or not. For now, as long as I have the card, I'm keeping it.
1980s: 1988 Team Issued #17 Mark Grace The Cubs gave this set of cards away at Wrigley Field on Wednesday, August 24. They beat the Astros that day 3-2 and Grace went 1-4. The 1988 season was Grace's rookie year, so this card would have been one of, if not the, first card of Grace as a major leaguer.
1990s: 1995 Starting Lineup Sammy Sosa The card shows Sammy taking a swing in 1994. He still looks like the skinny pre-juice Sammy.
2000s: 2003 Topps Traded #39 Paul Bako The Cubs picked up Bako in an off-season trade with the Brewers prior to the 2003 season. He spent the year as a back-up to Damian Miller and played in 70 games. He was the typical good-glove no-hit backup catcher.
2010s: 2011 Topps Limited Edition #481 Randy Wells This card comes from the Limited Edition Factory Set, which was only available via the Diamond Giveaway gimmick Topps had going in 2011. The card has a special logo in the upper left corner and some special writing above the name. An arm injury cost Wells two months of the season. He went 7-6 with a 4.99 ERA.