On this day in 1991, history was made when three generations of Carays were in the booth together. Harry, Skip, and Chip Caray all did the Cubs-Braves game at Wrigley Field.
Tom Glavine pitched a complete game that day, and the Braves beat the Cubs 5-3. The Cubs did make it interesting in the 9th inning, thanks to a 2-run homer by Andre Dawson that cut the lead to two runs. Chico Walker doubled after that to bring up the potential tying run in the person of Shawon Dunston.
You can be sure there was disdain in Harry's voice on the call of Dunston's at bat: "He popped it up."
Over the next few years, Harry and Skip continued to share time together in the booth whenever the Braves and Cubs played, but 1998 was supposed to be the year that Harry and his grandson Chip shared the booth the whole season for the Cubs. Unfortunately, Harry passed away before the season started. Instead of working with him, Chip replaced his grandfather.
In 2007, Chip Caray signed with TBS, hoping to broadcast some games with his dad. They did have a little bit of time together, but not much. Skip Caray passed away in 2008. The following year, Chip was hired to be the full-time voice of the Atlanta Braves on Fox Sports South, essentially replacing his father too.