I'm not exactly sure what the criteria for unlocking this is, but I got my first Smash Headline on the Dining Room hole 'Down the Hatch'. This was during the 4th tour.
I got a platinum medal and a score of $356,915 - and hit a double smashdown by destroying all five wine bottles and ten tables.
One of the loading tips says it's score-related, so maybe involves getting over $350,000