What classic board game uses a pop-up bubble to roll dice and was first released in the 1960s?

Trouble is the answer. First released in the 1960s and originally associated with Kohner Brothers, Trouble became known for its plastic game board, colored player tokens, and Pop-O-Matic die roller, a clear pop-up bubble that made the dice roll part of the board itself.

The Pop-O-Matic Dice Roller

The Pop-O-Matic feature is the design detail that separates Trouble from many other roll-and-move board games. Players press the clear plastic bubble, which pops the enclosed die and rolls it without letting it leave the board. That made the game more self-contained, helped prevent the die from being lost, and gave each turn a simple physical action.

A Race Game Built Around Simple Movement

Trouble is a race-style family board game in which players move colored pieces around the board and try to get all of their pieces home. Its rules are easy to understand, but the built-in die roller gives the game a distinctive sound and feel. Trouble later became connected with Milton Bradley and Hasbro through brand ownership and distribution history, but the Pop-O-Matic bubble remained its defining feature.