By Jerry Pearce

“Recording with Billy May is like having a bucket of cold water thrown in your face.” — Frank Sinatra

No truer statement in terms of musical orchestration was ever spoken by the Chairman of the Board himself. Second in quality of collaboration only to fellow Sinatra sideman Nelson Riddle, all-around genius Billy May was considered the premiere arranger for the fast driving tempo of brassy big band orchestral arrangements, a legendary reputation he maintained until his untimely death at the age of eighty-seven in 2004.

Although Riddle outranks May slightly when looking at the number of albums they both made over the years with Frank Sinatra, the six projects Sinatra and May joined forces on in the years between the late 1950s and the late 1970s represent not only the pinnacle of May’s arranging for a vocalist, but perhaps the hardest swing-based music Sinatra recorded in his entire career.

It began in October 1957 with the recording of the album “Come Fly With Me” for Capitol Records. Designed for the listener as a trip around the world via a fine travelogue collection of locale-based songs, it was one of the most relevant examples of Sinatra’s recording method of the “concept” album, basing a number of songs around a certain theme (in this case, of course, travel).

The title tune, written for Sinatra by the team of Sammy Cahn and Jimmy Van Heusen, would become a definitive career performance and Sinatra concert staple for years to come, even chosen for a studio re-recording on the occasion of the singer’s fiftieth birthday in 1965.

While the musical program varied between the hard drive of the brass (“Brazil,” “Isle of Capri,” “On The Road to Mandalay”) and the tender sentiment of the strings (“Moonlight in Vermont,” “April in Paris,” “Autumn in New York”), the overall album would set the standard for the caliber of their work to follow.

Capitol would be the setting for their second pairing in January 1959. Dropping the string section and focusing solely on the wailing magic of brass and reeds, “Come Dance With Me” would result in another dynamo for both singer and arranger. Another original title tune written by Cahn and Van Heusen would open the record, setting a breakneck pace for intricate, high octane readings of another twelve classics, including “Something’s Gotta Give,” “Day In, Day Out,” “I Could Have Danced All Night,” and “Too Close For Comfort,” decelerating only to recite another song written by Cahn/Van Heusen at Sinatra’s request for this album, the wistful “Last Dance.” The album charted at the number one position on the Billboard chart, and took multiple honors at the Grammy awards of 1960, including Album of the Year and Best Male Vocal Performance for Sinatra and Best Arrangement for May.

In the midst of his success, a combination of desire to have even more artistic freedom as well as souring relations between Sinatra and Capitol Records spearheaded the campaign to start his own label. After months of planning, in December of 1960, Sinatra fired off his own Reprise Records label with the release of “Ring-A-Ding-Ding,” a bombastic, jazz-infused debut with a collection of tunes arranged by Johnny Mandel, followed by the retrospective “I Remember Tommy” album recalling the days of his association with the Tommy Dorsey Orchestra, arranged by Dorsey veteran Sy Oliver.

With these two successful albums cementing the new label’s presence on the album market, it pained the temperamental singer to return to Capitol to fulfill the remainder of his recording contract with the company. With Capitol and Reprise sessions overlapping, Sinatra set out, begrudgingly to create the last three albums of his contract and be rid of the former company for good. One of these albums would be recorded with Billy May, what would be the third in their “Come With Me” series. In the same time frame, he would also be working with the arranger on an album of similar material at Reprise.

With a slightly hostile air building above the studio and some legal wrangling’s to follow, Sinatra and May would turn out some of the most exemplary work of their careers.

The third effort at Capitol, “Come Swing With Me,” got off to a roaring start with the ironic recording of “On The Sunny Side of the Street” in March 1961. Although he was at dire straits at this point with the label, the quality of his voice on this album bears no evidence as to the ilk brewing behind the scenes. Sinatra banged out twelve songs over the course of three days, including great up-tempo versions of “Almost Like Being In Love,” “American Beauty Rose,” “That Old Black Magic,” “Lover,” and “Paper Doll.” Crafting a prerequisite, May includes another slow-mover in the program, a brass-heavy arrangement of “Sentimental Journey,” and it stands as an equal to “Last Dance” on the previous Sinatra-May album.

With the opener, “Day By Day,” the listener will hear brass notes succinctly zinging from both sides of the soundtrack on the bridge. Utilizing Capitol’s new stereophonic recording process, Billy May positioned instruments in the studio in such a way that it gives the listener the impression of being up the bandstand with the singer and arranger, with horns blasting off to the left and the right. Assisted by ghost writer Heinie Beau on a few of the charts, the album was released in later 1961.

Nearly two months to the day he began work on the Capitol album, Sinatra was in studio at United-Western in Los Angeles working on the Reprise project with May. Another three days of recording sessions would warrant another twelve songs, and arguably, the superior of the two albums. Breaking tradition with their two later Capitol projects, “Dance” and “Swing,” May employs a small string section in tandem with the brass, utilized well on the ballad “Don’t Cry Joe (the slow mover in this package), and giving an extra overflowing bite to the swingin’ charts of “Granada” and “You’re Nobody Til’ Somebody Loves You.”

Other standout charts on this album include “It’s A Wonderful World,” “Don’t Be That Way,” “Moonlight On The Ganges,” and a great version of “Have You Met Miss Jones?” Sinatra had earlier attempted the tune for “Ring-A-Ding-Ding!” but his dissatisfaction with the Johnny Mandel arrangement left it shelved until it was handed to May for this project, where the arranger delivers an orchestration much more on par to Sinatra’s phrasing and liking. Indeed, while both of these albums are superb, the Reprise effort triumphs.

Assigned the title “Swing Along With Me,” with a cover of a fiercely blue eyed Sinatra peeking through swinging yellow bar doors, copies of the new album were barely off the record press when Capitol slammed Reprise with an injunction, charging that their new release was so close in title and sound to their album that some aspects of it would have to be changed. A court ordered in favor of Capitol, requiring Reprise to change the titles on all albums produced forthcoming. “Swing Along With Me” would become “Sinatra Swings,” although many years later, when the compact disc came into being, the album was released in the new format with its original title intact.

The completion of the Reprise album would signal the end of album making between Sinatra and Billy May for the better part of the 1960s. Although they would work on a few single song arrangements together (May’s 1964 arrangement of “Luck Be A Lady” a particular highlight), their next album wouldn’t follow until 1967, when May arranged eight songs for Sinatra for an album featuring Frank backed by the Duke Ellington Orchestra (“Francis A. & Edward K.”).

Another twelve years would elapse following, with their final album project together taking form in 1979 with the first part of the three-disc “Trilogy” album, the ten tracks recorded for the “Past” section of “Trilogy” recalling much of the great sounds that Sinatra and May made at both Capitol and Reprise in the late 50s/early 60s. Quite fittingly, Sinatra’s final full recording session for Reprise Records took place in 1988, with Frank recording a Billy May arrangement of the tune “My Foolish Heart,” May himself wielding the baton before the orchestra for his frequent collaborator for once last time. A swingin,’ slightly jazzy close (with trumpet solos by Jack Sheldon) to an awesome musical partnership.

“The Song Is You” is one particular tune that May arranged for Sinatra twice, both for “Come Dance With Me” in 1959 and “Trilogy” in 1979. Twenty years between these performances with variances in both vocals and orchestration, but the singer’s words that opened this article will ring true when you listen to either version: listening to a Sinatra song with a bombing Billy May arrangement really is like an eye-opening, cold bucket of water to the face!

Until next time, Sinatra lovers!

Jerry Pearce is an amateur singer in the vein of Frank Sinatra, Perry Como, and Dick Haymes and has released two discs of standards music, Crossroads in 2010, and One Summer Night in 2016. Samples of his music can be heard on his YouTube Channel. To purchase his CDs use the form box below.

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