Cyndi Lauper and David Thornton – Est. $38 million

Cynthia Ann Stephanie Lauper has enchanted us over the decades with some memorable numbers like Girls Just Want to Have Fun, All Through the Night, Time After Time, and True Colors. She had her wedding with the Home Alone 3 actor David Thornton in the year 1991, and the two have stayed loyal to one another for the past 28 years.

Lauper and Thornton were in two minds regarding whether to part ways with their Connecticut property, but in the due course of time, they eventually put the French Colonial style residence up for sale at an approximate price of $1.25 million. In spite of facing bankruptcy once, Lauper has piled on $30 million, while David has amassed around $8 million. Together, they are sitting on a combined sum of $38 million.