What building was built earlier,  Manhattan Life Insurance Building or 15 Penn Plaza?
15 Penn Plaza 15 Penn Plaza, also known as the Vornado Tower, is a proposed 68-story tower in the Midtown Manhattan section of New York City planned by Vornado Realty Trust. It would have 430 units and 2,050,000 square feet (190,451 m²) of floor space. The Hiller Group is the designer. Despite only having 68 floors, it would be just 10 m shorter than the Empire State Building, which has 102 floors.
Woolworth Building The Woolworth Building, at 233 Broadway, Manhattan, New York City, designed by architect Cass Gilbert and constructed between 1910 and 1912, is an early US skyscraper. The original site for the building was purchased by F. W. Woolworth and his real estate agent Edward J. Hogan by April 15, 1910, from the Trenor Luther Park Estate and other owners for $1.65 million. By January 18, 1911, Woolworth and Hogan had acquired the final site for the project, totaling $4.5 million. More than a century after its construction, it remains, at 241.4 m , one of the 100 tallest buildings in the United States as well as one of the 30 tallest buildings in New York City. It has been a National Historic Landmark since 1966, and a New York City landmark since 1983.