During its heyday in the 1950s and 60s, the second Crawford Grill venue hosted local and nationally-recognized acts, including jazz legends Art Blakey, Charles Mingus, Max Roach, Miles Davis, John Coltrane, Bill Evans, and Kenny Burrell.

The Crawford Grill was one of many black-owned neighborhood clubs in the Eastern United States that supported a tour circuit for small jazz ensembles during the genre's "golden age."

The Crawford Grill can be best understood as the outgrowth of a broader set of social institutions that flourished in the Hill District neighborhood in the early 1900s.

The high standard of entertainment was established by pianist Earl Hines, who began his career as a jazz musician in the Hill District when he was hired by bandleader Lois Deppe to perform at the Leader House, and violinist Vernie Robinson at the Collins Inn.

[11] According to Ralph Proctor, a professor of African American History, "The Grill provided a place of elegance in an area outsiders tended to think of as down-trodden."

[13] The second-floor club opened in March 1935 with entertainment produced by Billy Maxey, featuring New York and Ohio performers.

[4] With his business partner Joseph Robinson, Greenlee opened a second venue on the corner of Wylie Avenue and Elmore Street, approximately ten blocks east of the original location.

[16] Located on the corner of Bidwell Street and Pennsylvania Avenue in the Manchester neighborhood of Pittsburgh, this club closed in just seven years.

[12] Capitalizing on the famous Crawford Grill name, Les Montgomery and Tom Burley opened a new venue at 125 W. Station Square Drive in the Freight House Shops, in Pittsburgh's South Side neighborhood.

[20] Despite being awarded "best soul food" by a local paper three years running, the new club suffered from lack of foot traffic, closing its doors on January 7, 2006.

[23] Calling their initiative the "Crawford Grill Revitalization Project,"[23] the group has stated it aims to preserve the legacy of the building through restoration efforts and the establishment of a new restaurant and nightclub.