65 years ago, Frank Sinatra came close to the First Grammy

Controversy over winners and losers has been part of the Grammy experience since the first presentations, which took place on May 4, 1959 — 65 years ago today. The biggest controversy that year had to do with a disappointing performance by Frank Sinatra, who was coming off one of the greatest years of his long career. Had two No. 1 albums on the Billboard 200 in 1958 — Come fly with me and Frank Sinatra only sings for the lonely.

Sinatra was the leading Grammy nominee of the year, 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 “Magic”). The star only won one award – and that wasn't even for his song. He won Best album Cover for his art direction Only the Loners.

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

Sinatra's two album of the year nods undoubtedly worked against him in this category. (The rules have since changed so that an artist can only have one nomination as lead artist in most categories.) The award went to Mancini for Music by Peter Gunn. The album featured music from a weekly detective television series that debuted in September 1958 and ran for three seasons. (Mancini's album was released after the cut-off for the 1958 awards on December 31, 1958. How it was nominated in the first place is a mystery. It was probably just a prank slipped by the small staff of the fledgling Recording Academy. The many tools they use people 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 the same album. Mancini won 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 Sinatra's two entries. “Witchcraft” and “Catch a Falling Star” were both nominated for record of the year, but lost out to Domenico Modugno's lounge music staple “Nel Blu Dipinto Di Blu (Volare).

In addition to Record of the Year, Modugno took home Song of the Year for “Volare”, which is, to date, 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 had only one more entry on the Hot 100, 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., creator of The Chipmunks.

Fitzgerald won two awards for different installments of her celebrated Book of songs 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, solo.

Count Basie won awards in different genres for the same album (something that couldn't happen today). It won Best Performance by a Dance Group and Best Jazz Performance, Group, both for Basie.

Bagdasarian won best comedy and best children's recording for both “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 date, the only children's or comedy recording to be nominated in this category.

The Grammys were the last of the four EGOT-level awards to begin, arriving just over a decade after the launch of the third of the four, the Emmys. 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 January 25, 1949 at the Hollywood Athletic Club.

The first Grammys were black tie. “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 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 in black tie back then, although like so much else, that would eventually change.” Farnon became the academy's executive vice president. She led the academy for 35 years until her retirement in 1992 – an unprecedented pioneer for powerful women in the music industry.

Sinatra didn't let his disappointing performance at the 1st Annual Grammy Awards keep him down for long. It earned three more nominations the following year, this time winning album of the Year for Come Dance With Me! He would win this award twice more, 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 February 4, 2024, Taylor Swift became the first four-time winner.