Can a Boring City Become Cool—With a Little Help From Taylor Swift?

SINGAPORE—When it comes to fun, Singapore’s government is super serious.

For decades, the manufacturing and trading hub had been known for being a city that was all work and no play—epitomized by a government decision in the 1990s to ban the sale of chewing gum, after discarded pieces lodged between train doors and delayed the subway. One quip went that Singapore was “the world’s only shopping mall with a seat at the United Nations.”