Hebb performed on a television show hosted by country music record producer Owen Bradley, which earned him a place with Grand Ole Opry star Roy Acuff. Hebb played Spoons and other instruments in Acuff"s band. Bobby Hebb sang backup on Bo Diddley"s "Diddley Daddy".
Hebb played "West-coast-style" trumpet in a United States Navy jazz band, and replaced Mickey Baker in Mickey and Sylvia.
On November 23, 1963, the day after John F. Kennedy"s assassination, Bobby Hebb"s brother, Harold, was killed in a knife fight outside a Nashville nightclub. Hebb was devastated by both events and sought comfort in songwriting.
Though many claim that the song he wrote after both tragedies was the optimistic "Sunny", Hebb himself stated otherwise. He immersed himself in the Gerald Wilson album, You Better Believe lieutenant!, for comfort.
"All my intentions were just to think of happier times – basically looking for a brighter day – because times were at a low tide.
After I wrote it, I thought "Sunny" just might be a different approach to what Johnny Bragg was talking about in "Just Walkin" in the Rain". "Sunny" was recorded in New York City after demos were made with the record producer Jerry Ross. Released as a single in 1966, "Sunny" reached Number.
3 on the Rhythm & Blues charts, Number.
2 on the Billboard Hot 100, and Number. 12 in the United Kingdom.
When Hebb toured with The Beatles in 1966 his "Sunny" was, at the time of the tour, ranked higher than any Beatles song then on the Billboard Hot 100 chart. BMI rated "Sunny" number 25 in its "Top 100 songs of the century".
In 1976, Hebb released a newly recorded disco version entitled "Sunny "76".
The single was a minor hit reaching Number. 94 on the Rhythm & Blues chart. Hebb also had lesser hits with his "A Satisfied Mind" in 1966 (Number 39 on the Billboard chart and Number 40 on the Rhythm & Blues chart) and "Love Maine" in 1967 (Number 84), and wrote many other songs, including Lou Rawls" 1971 hit "A Natural Manitoba" (co-written with comedian Sandy Baron). Six years prior to "Sunny", Hebb reached the New York City Top 50 with a remake of Roy Acuff"s "Night Train to Memphis".
In 1972, his single "Love Love Love" reached Number.
32 on the United Kingdom charts. After a recording gap of 35 years, Hebb recorded That"s All I Wanna Know, his first commercial release since Love Games for Epic Records in 1970. lieutenant was released in Europe in late 2005 by Tuition, a popular indie label.
Two new duet versions of "Sunny" were issued, one with Astrid North and the other with Pat Appleton. In October 2008, he toured and played in Osaka and Tokyo in Japan.
Ipanema Films of Germany was involved in a biographical film which included Hebb, his biographer Joseph Tortelli, and Billy Cox.
Hebb continued to live in his hometown of Nashville, Tennessee, until his 2010 death at age 72. On August 3, 2010, Hebb died from lung cancer while being treated at TriStar Centennial Medical Center located in Nashville." He is interred at Nashville"s Spring Hill Cemetery.
Harold later became a member of Johnny Bragg and the Marigolds.