The retail space on the ground floor, mezzanine and basement has held a variety of businesses, in succession over the building's history, among the longest-lasting ones being a drugstore (1912–1927), a Sherman Clay piano and music store (1930–1974), and an independent shoe store (2000–2016).

[5] The building was constructed as the new headquarters for the Portland-based retail and wholesale pharmaceutical companies owned by Louis G. Clarke (1855–1943) and William W. Woodward (1863–1940), and its name – originally written as "Wood-Lark" Building[1][6] – was formed by combining parts of the two men's names.

In 1906, Clarke formed a new partnership with William Woodward, who had already been working for the company since 1882, to establish a wholesale drug business.

[7] Designed by Portland-based Doyle, Patterson & Beach, the Woodlark Building uses Late 19th and Early 20th Century Commercial style, also featuring "strong Beaux-Arts influence in the elaborate cornice and other detailing.

Other changes made at that time included a redesign and relocation of the building's main entry point, from West Park Street (now SW 9th Avenue) to a new entrance on Alder Street, at the building's southeast corner.

Sherman Clay & Company, a seller of musical instruments and sheet music, moved into the space in January 1930 from a location elsewhere in downtown, occupying the basement, ground floor and mezzanine levels, initially under a 10-year lease.

[12] In April 2014, the building was acquired by Arthur Mutal, a Portland real estate developer, at a cost of $8.65 million.

The planned renovation and conversion was expected to cost $30 million, funded by NBP Capital, Provenance Hotels and Arthur Mutal LLC.