Bill Henderson, jazz vocalist and actor, died of natural causes in Los Angeles on Sunday. He was 90.

Henderson’s break came in 1957 when he recorded for the Vee-Jay label and recorded his first album “Bill Henderson Sings” in 1959. Henderson sang with the Ramsey Lewis Trio, Dizzie Gillespie, Count Basie, Frank Sinatra, Tony Bennett, Quincy Jones, and the Charlie Haden Quintet. His 1963 recording “Bill Henderson with the Oscar Peterson Trio” remains a classic in the jazz vernacular. He was a fixture on the Playboy circuit in the 1970s and appeared often at many jazz festivals, including Playboy Jazz at the Hollywood Bowl, Monterey Jazz and the Litchfield Jazz Festival.

“Henderson’s phrasing is virtually his own copyright,” Leonard Feather observed. “He tends to space certain words as if the syllables were separated by commas, even semicolons; yet everything winds up as a perfectly constructed sentence.” Henderson’s voice was deliberate and thoughtful, feeling all the way through, but still natural and smooth.

Although known mostly for his music, Henderson also ventured into acting. His stage credits include film and television projects such as “City Slickers,” “Maverick,” “Lethal Weapon 4,” “Buckaroo Banzai,” “White Men Can’t Jump,” “Smiling Fish & Goat on Fire,” “ER,” “Hill Street Blues,” “The Twilight Zone,” “Happy Days,” “Sanford and Son,” “The Jeffersons,” “Good Times,” “MacGyver,” “Benson,” “NYPD Blues” and “My Name Is Earl.”

William Randall Henderson made his show business debut as a singer and dancer at age 4. His father taught him the value of singing softly. He spent his teens and 20s fluctuating between school, day jobs and trying to make it as a singer. A stint in the Army provided him an opportunity to work with Vic Damone, and in 1956, Henderson made his way to New York, where he soon became part of the jazz community.

As Henderson aged he resumed singing and toured in his 80s, appearing at the Kennedy Center, the Hotel Algonquin’s famed Oak Room and at Lincoln Center. During this period, he released a self- produced CD entitled, “Beautiful Memory,” co-produced by Lynne Robin Green.

Henderson raised his daughter, Mariko, as a single father. He is survived by her and by his granddaughter, Mya; his son-in-law, Marc; his nephew, Finis E. Henderson III; and his niece, Henreene Hyler.