I've got 14,745 Cubs cards from 120 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1974 Topps #484 Carmen Fanzone Topps used a picture from 1972 for this card.
I'm guessing that the '73 and '74 cards have pictures from the same photo shoot at Shea.
1980s: 1989 Sportflics #216 Damon Berryhill I wish I could figure out a way to scan these so you get a clear look at each of the pictures. The two-in-one look is not a good one.
1990s: 1993 Topps Black Gold #4 Andre Dawson Topps went to all the trouble of making a Black Gold card for Dawson, but he didn't play for the '93 Cubs. Instead, he spent the year in Boston as their DH.
2000s: 2004 Bazooka #257 Ryan Harvey The Cubs took Harvey in the first round (6th overall) of the 2003 draft. He was a major bust, never getting above AA.
2010s: 2013 Allen & Ginter #307 Darwin Barney The 2013 season was the beginning of the end of Barney's time with the Cubs. He was coming off of a Gold Glove winning season, but his bat had turned to mush. He hit just .208 and the brass realized they needed more that a glove at second base.