Designed by Holabird & Root, the Palmolive Building was completed in 1929 as the home of the Colgate-Palmolive-Peet Company.

[2] During the time that Playboy was in the building, the word P-L-A-Y-B-O-Y was spelled out in 9-foot (2.7 m) illuminated letters on the north and south roofline.

[3] The building was designated a Chicago Landmark in 2000,[4] and it was added to the federal National Register of Historic Places in 2003.

In 2001, the building was sold to developer Draper and Kramer who, with Booth Hansen Architects, converted it to residential use, with the first two floors dedicated to upscale office and retail space.

Notable residents of the building include Vince Vaughn, who bought a 12,000-square-foot (1,100 m2) triplex penthouse encompassing the 35th, 36th and 37th floors for $12 million.