As at his earlier company, Riverside, producer Orrin Keepnews had little trouble attracting top-flight jazz artists to his Milestone label. Within a few years of its 1966 founding, Sonny Rollins, Joe Henderson, Gary Bartz, and McCoy Tyner all joined the Milestone family.

Keepnews and Milestone moved from New York to Berkeley in 1972 to become a part of Fantasy, Inc., where he soon launched the successful solo recording career of Brazilian vocalist Flora Purim and worked with a wide array of artists in his capacity as Director of Jazz A&R.

Although Keepnews departed the company in the early Eighties, Milestone remains an active label with a roster that includes, Arturo O'Farrill, Manny Oquendo & Libre, Joe Locke, Jimmy McGriff, Hank Crawford, George Mraz, and Sonny Rollins.