He played piano in big bands led by Tex Beneke and Ray McKinley, but concentrated on valve trombone from when he moved to the Claude Thornhill orchestra in the early 1950s.

During the 1950s and 1960s, Brookmeyer played in New York clubs, on television (including being part of the house band for The Merv Griffin Show), and on studio recordings, as well as arranging for Ray Charles and others.

[1] His eighth Grammy Award nomination was for an arrangement from the Vanguard Jazz Orchestra's album, Forever Lasting, shortly before his death.

[1][6] One notable element of Brookmeyer's compositional style is his use of contemporary classical writing techniques in his works for big bands and jazz ensembles.

[7] Some examples of 20th-century classical compositional techniques used in Brookmeyer's jazz pieces are: With Manny Albam With Steve Allen With Chet Baker With Teddy Charles With Al Cohn With Stan Getz With Jimmy Giuffre With Jim Hall With Nancy Harrow With Woody Herman With Gary McFarland With Gerry Mulligan With Jimmy Raney With George Russell With Don Sebesky With Bud Shank With Zoot Sims With Clark Terry With others