After his graduation from Rumson High School, Riddle spent his late teens and early 20s playing trombone in and occasionally arranging for various local dance bands, culminating in his association with the Charlie Spivak Orchestra. In 1943, Riddle joined the Merchant Marine, serving at Sheepshead Bay, Brooklyn, New York for about two years while continuing to work for the Charlie Spivak Orchestra.[citation needed]
Riddle studied orchestration under his fellow merchant mariner, composer Alan Shulman. After his enlistment term ended, Riddle traveled to Chicago to join Tommy Dorsey's orchestra in 1944, where he remained the orchestra's third trombone for eleven months until drafted by the Army in April 1945, shortly before the end of World War II. He was discharged in June 1946, after fifteen months of active duty. He moved shortly thereafter to Hollywood to pursue a career as an arranger, and spent the next several years writing arrangements for multiple radio and record projects.[3]: 69 In May 1949, Doris Day had a #2 hit, "Again", backed by Riddle.
Capitol years
In 1950, Riddle was hired by composer Les Baxter to write arrangements for a recording session with Nat King Cole; this was one of Riddle's first associations with Capitol Records. Although one of the songs Riddle had arranged, "Mona Lisa," soon became the biggest selling single of Cole's career, the work was credited to Baxter.[3]: 81 However, once Cole learned the identity of the arrangement's creator, he sought out Riddle's work for other sessions, and thus began a fruitful partnership that furthered the careers of both men at Capitol.
During the same year, Riddle also formed a friendship with Vern Yocum (born George Vernon Yocum), a big band jazz musician (and brother of Pied Piper Clark Yocum) who would transition into music preparation for Frank Sinatra and other entertainers at Capitol Records. A collaboration followed, with Vern becoming Riddle's "right hand" as copyist and librarian for the next thirty years.
In 1953, Capitol Records executives viewed the up-and-coming Riddle as a prime choice to arrange for Frank Sinatra. Sinatra was reluctant, however, preferring instead to remain with Axel Stordahl, his long-time collaborator from his Columbia Records years. When the success of the first few Capitol sides with Stordahl proved disappointing, Sinatra eventually relented and Riddle was called in to arrange his first session for Sinatra, held on April 30, 1953. The first product of the Riddle-Sinatra partnership, "I've Got the World on a String", became a runaway hit and is often credited with relaunching the singer's slumping career. Riddle's personal favorite was a Sinatra ballad album, one of his most successful recordings, Only the Lonely.
For the next decade, Riddle continued to arrange for Sinatra and Cole,[5] in addition to such Capitol artists as Kate Smith, Judy Garland, Dean Martin, Keely Smith, Sue Raney, and Ed Townsend. He also found time to record his own instrumental discs, released on Capitol in both 45 RPM single, and LP album format. Riddle's most successful tune was "Lisbon Antigua", released in November 1955, which reached and remained at the #1 position for four weeks in 1956. Riddle's most notable LPs were Hey ... Let Yourself Go (1957) and C'mon ... Get Happy (1958), both of which peaked at a respectable number twenty on the Billboard charts. In 1959, he won the Grammy Award for Best Musical Composition First Recorded and Released in 1958 (over 5 minutes duration) at the inaugural award ceremony for Cross Country Suite.[6]
While at Capitol, Riddle continued his successful career arranging music for film, most notably with MGM's Conrad Salinger on the first onscreen duet between Bing Crosby and Sinatra in High Society (1956), and the 1957 film version of Pal Joey directed by George Sidney for Columbia Pictures.