She made her recording debut for the Keynote label that December with “Evil Gal Blues”, written by Leonard Feather and backed by Hampton and musicians from his band, including Joe Morris (trumpet) and Milt Buckner (piano). Both that record and its follow-up, “Salty Papa Blues”, made the Billboard “Harlem Hit Parade” in 1944. In December 1945 she made a series of twelve recordings for Apollo Records, 10 of which were issued, featuring the “Lucky Thompson All Stars.”

In 1950, Dinah Washington performed at the sixth famed Cavalcade of Jazz concert held at Wrigley Field in Los Angeles which was produced by Leon Hefflin, Sr. on June 25. Also featured on the same day were Lionel Hampton, PeeWee Crayton’s Orchestra, Roy Milton and his Orchestra, Tiny Davis and Her Hell Divers, and other artists. 16,000 were reported to be in attendance and the concert ended early because of a fracas while Lionel Hampton played “Flying High”. Washington came back to perform at the twelfth Cavalcade of Jazz also at Wrigley Field in Los Angeles on September 2, 1956. Also performing that day were Little Richard, The Mel Williams Dots, Julie Stevens, Chuck Higgin’s Orchestra, Bo Rhambo, Willie Hayden & Five Black Birds, The Premiers, Gerald Wilson and His 20-Pc. Recording Orchestra and Jerry Gray and his Orchestra.

In 1959, she had her first top ten pop hit, with a version of “What a Diff’rence a Day Made”, which made Number 4 on the US pop chart. Her band at that time included arranger Belford Hendricks, with Kenny Burrell (guitar), Joe Zawinul (piano), and Panama Francis (drums). She followed it up with a version of Irving Gordon’s “Unforgettable”, and then two highly successful duets in 1960 with Brook Benton, “Baby (You’ve Got What It Takes)” (No. 5 Pop, No. 1 R&B) and “A Rockin’ Good Way (To Mess Around and Fall in Love)” (No. 7 Pop, No. 1 R&B). Her last big hit was “September in the Rain” in 1961 (No. 23 Pop, No. 5 R&B).

Washington was well known for singing torch songs. In 1962, Dinah hired a male backing trio called the Allegros, consisting of Jimmy Thomas on drums, Earl Edwards on sax, and Jimmy Sigler on organ. Edwards was replaced on sax by John Payne. A Variety writer praised their vocals as “effective choruses”.

Washington’s achievements included appearances at the Newport Jazz Festival (1955–59), the Randalls Island Jazz Festival in New York City (1959), and the International Jazz Festival in Washington D.C. (1962), frequent gigs at Birdland (1958, 1961–62), and performances in 1963 with Count Basie and Duke Ellington.

Recordings by Dinah Washington were inducted into the Grammy Hall of Fame, which is a special Grammy award established in 1973 to honor recordings that are at least twenty-five years old, and that have “qualitative or historical significance.”