1900s - 1970s: 1969 Topps Stamps Ron Santo These were not inserts but sold separately. You got 12 stamps, a team album, and some gum for a nickel. Santo was one of the ten Cubs in the set.
1980s: 1989 Topps Big #60 Damon Berryhill I consider the Big set as Topps first attempt at something Heritage-like. The oversized cards matched the size of the original Topps sets of the early '50s. But apparently size doesn't matter and the brand lasted only a few years. It seems to be the design that is more important and Heritage has been a hit since its release.
1990s: 1993 Stadium Club #285 Mike Morgan Morgan had the best year of his career the year before this card came out, going 16-8 with an ERA of 2.55. He was never close to that again. In '93 he dropped to 10-15 and his ERA ballooned to 4.03.
2000s: 2007 Topps Update #57 Carlos Marmol Marmol was lights-out as the 8th inning guy in 2007. He had 96 strike outs in 69 innings.
2010s: 2016 Topps Holiday #13 Aroldis Chapman A guy from Cuba pitching in the snow... go figure!