The hotel was designed to comply with city regulations that required deep setbacks at the base, as well as large illuminated signs.

The City Investment Fund, a joint venture between Morgan Stanley Real Estate and Fisher Brothers, bought the hotel in 2006 and renovated it again two years later.

[3] Just prior to the hotel's construction, the site had contained six pornographic businesses owned by Michael Zaffarano,[4] including the Pussycat Cinema and the Kitty Kat and Mardi Gras Topless Disco.

The American Management Association's Executive Conference Center, is on the sixth through eighth floors with a total of 88,066 square feet (8,181.6 m2).

[16] The hotel was designed to comply with city regulations that required deep setbacks at the base, as well as large illuminated signs.

[7] Accordingly, the hotel rooms are deeply set back from Broadway, and the first seven stories were initially planned to contain curving signs.

[27][28] Holiday Inn originally reserved six floors for business patrons, who would pay an additional fee for extra services such as complimentary breakfast.

[29] To attract guests, each suite was designed with technologically advanced amenities of the time, such as modem connections and phone lines, as well as bathrooms clad with marble.

[34] During the decade, several hotels were developed around Times Square,[18][35] as well as in New York City in general, as a result of growing tourism.

[36] These hotel developments were spurred by the success of the nearby New York Marriott Marquis, which had an occupancy rate of over 80 percent across nearly 2,000 rooms.

[46] The CPC approved a planning regulation that September, which required large new developments in Times Square to set aside about five percent of their space for "entertainment uses", such as broadcast studios or ground-floor stores.

[18] The Holiday Inn Crowne Plaza planned to charge a minimum of $175 per night for a single room, making it more expensive than its competitors nearby.

[19][21] Nonetheless, Holiday Inn projected that the hotel would be profitable because the company already had a large number of frequent guests and business clients.

[29] By 1989, the number of annual visitors to New York City had decreased for the first time in eight years due to the effects of Black Monday.

[52] According to Silberstein, 129 guests made reservations for New Year's Eve in the first twelve hours of its operation, even though the hotel did not conduct any advertising.

[16] It was one of several new hotels in the Times Square area with a combined 4,200 rooms,[53] even as visitation rates in the city remained sluggish.

[57][58] The Holiday Inn Crowne Plaza was largely staffed by union workers, with the Broadway Grill being the only exception.

The hotel's office space had also remained empty until the same year, when the American Management Association indicated its intent to sign a 150,000-square-foot (14,000 m2) lease there.

[17] Among the advertisers on the Crowne Plaza's facade was the Poland Spring Corporation, which in 1998 signed a three-year lease for a curved billboard at 48th Street and Broadway.

[70][71] Around the same time, the area evolved into a business district and there was growing demand for meeting space, as well as numerous new restaurants.

[73] The City Investment Fund, a joint venture between Morgan Stanley Real Estate and Fisher Brothers, acquired the Crowne Plaza in 2006 for $362 million.

[76] Two years later, the hotel conducted an $85 million renovation on its lobby, restaurants, guest rooms, and meeting space.

[79] After the renovation was completed, the Crowne Plaza saw a lower occupancy rate than other hotels, in part because of decreased tourism.

[12] The next year, Krispy Kreme Doughnuts began building a store in the retail space,[85][86] which opened in September 2020.

[89] The Crowne Plaza shuttered in March 2020 due to the COVID-19 pandemic in New York City, and Vornado stopped paying rent on the ground lease.

[96] Vornado, which wanted to sell its stake to Penson, claimed that the purchase violated its right of first refusal and sued SL Green.

[104] When the hotel was completed, Anne Kates of USA Today wrote that the "sense of adventure" in Lapidus's design had received mixed reception.

[106] Paul Goldberger of The New York Times felt that the signs were more prominent than the building, saying that "it looks vastly better at night, when it is ablaze with neon, than it does during the day, when it seems only like a failed effort at elegance".

[61] Goldberger further elaborated his dissent in a 1992 article, saying the facade "has ugly, unfinished brick waiting for a sign that may not come for years, a glaring offense at the pedestrian.

"[107] Eve M. Kahn of The Wall Street Journal described the Holiday Inn Crowne Plaza as a "glitzy pink-granite-and-burgundy-glass jukebox" that sharply contrasted with the "restrained" design of 1585 Broadway.