65 Years Ago, Frank Sinatra Came Up Short at the First Grammys

Controversy over winners and losers has been part of the Grammy experience since the very first presentations, which took place on May 4, 1959 — 65 years ago today. The biggest controversy that year had to do with a disappointing showing by Frank Sinatra, who was coming off one of the biggest years of his long career. He had two No. 1 albums on the Billboard 200 in 1958 — Come Fly with Me and Frank Sinatra Sings for Only the Lonely.

Sinatra was the year’s top Grammy nominee, with six nods, including two for album of the year (the aforementioned albums) and two for best vocal performance, male (Come Fly with Me and “Witchcraft”). The star wound up winning just one award — and it wasn’t even for his singing. He took best album cover for his art direction of Only the Lonely.

Sinatra attended the event, which was held in the Grand Ballroom of the Beverly Hilton in Beverly Hills, Calif. — now best known for hosting the Golden Globes every year. (There was a simultaneous event in New York City for East Coast denizens.) Other attendees at the Beverly Hilton included Sinatra’s fellow Rat Pack members Sammy Davis Jr. and Dean Martin, as well as fellow nominees Henry Mancini and Peggy Lee. Comedian Mort Sahl served as MC.

Sinatra’s two nods for album of the year no doubt worked against him in that category. (The rules have since been changed so an artist can only have one nomination as a lead artist in most categories.) The award went to Mancini for The Music from Peter Gunn.  The album featured music from a weekly TV detective series that debuted in September 1958 and ran for three seasons. (Mancini’s album was released after the Dec. 31, 1958 eligibility cut-off for the 1958 awards. It’s a mystery how it was nominated in the first place. It was probably just a goof that slipped by the small staff at the fledgling Recording Academy. The many tools that people use today to quickly check facts didn’t exist back then, an era of rotary phones and 3 x 5 cards.)

In addition to album of the year, Mancini won best arrangement for that same album. Mancini went on to win 20 Grammys, which was, for many years, the most won by any artist. (That title is currently held by Beyoncé with 33 awards.)

Perry Como‘s silky “Catch a Falling Star” won best vocal performance, male, beating the two Sinatra entries. “Witchcraft” and “Catch a Falling Star” were both nominated for record of the year, but lost to Domenico Modugno‘s lounge music staple “Nel Blu Dipinto Di Blu (Volare).”

In addition to record of the year, Modugno took song of the year for “Volare,” which is, to this day, the only foreign-language song to win record or song of the year. “Volare” topped the Billboard Hot 100 for five weeks in 1958, though Modugno landed just one more Hot 100 entry, a song that peaked at No. 97.

There were just 28 categories at the first Grammys, the lowest number ever. There were five double winners — Mancini, Modugno, Ella Fitzgerald, Count Basie and Ross Bagdasarian Sr., the creator of The Chipmunks.

Fitzgerald won two awards for different installments of her celebrated Song Book series, a fitting tribute to this versatile singer. Ella Fitzgerald Sings the Irving Berlin Song Book won best vocal performance, female. Ella Fitzgerald Sings the Duke Ellington Song Book took best jazz performance, individual.

Count Basie won awards in different genres for the same album (something that couldn’t happen today). He took best performance by a dance band and best jazz performance, group, both for Basie.

Bagdasarian won best comedy performance and best recording for children, both for “The Chipmunk Song,” which was a No. 1 hit on the Hot 100. The smash was also nominated for record of the year. It is, to this day, the only children’s or comedy recording to be nominated in that category.

The Grammys were the last of the four EGOT-level awards shows to get underway, arriving a little more than a decade after the third of the four, the Emmys, rolled out. The first Oscars were presented on May 16, 1929 at the Hollywood Roosevelt Hotel. The first Tony Awards were presented on April 6, 1947 at the Waldorf-Astoria Hotel in New York. The first Primetime Emmys were presented on Jan. 25, 1949 at the Hollywood Athletic Club.

The first Grammys were a black-tie affair. “The Grammy Awards were a formal event from the beginning and very much in keeping with the times,” Christine Farnon, who was instrumental in organizing the first show, was quoted as saying in the 2007 coffee table book, And the Grammy Goes To… The Official Story of Music’s Most Coveted Award, written by David Wild. “As I recall, no one objected to dressing black-tie back then, though like so much else, that would change eventually.” Farnon went on to be the academy’s executive vice president. She ran the academy for 35 years until her retirement in 1992 — an undersung pioneer for powerful women in the music industry.

Sinatra didn’t let his disappointing showing at the 1st annual Grammy Awards keep him down for long. He landed three more nominations the following year, and this time won album of the year for Come Dance with Me! He would win that award two more times, for September of My Years (1966) and A Man and His Music (1967). This made him the first two-time winner and also the first three-time winner. On Feb. 4, 2024, Taylor Swift became the first four-time winner.