In the late 1950s, Calello was a member of Frankie Valli's group The Four Lovers, but left before the group was transformed into The Four Seasons. In 1962, he became the group's musical arranger. In 1965, he briefly filled in for Nick Massi (who was Calello's replacement in The Four Lovers five years earlier but had abruptly quit the band) while the band prepared Joe Long to take the role on a permanent basis.[4] Following his stint with the Seasons, he became a staff arranger/producer at Columbia Records. In 1968, he became an independent producer and arranger and a year later arranged Frank Sinatra's album Watertown, written by Bob Gaudio.
He has also composed film music, including the scores to Who Killed Teddy Bear (1965) and The Lonely Lady (1983). In 1992, he became principal arranger and assistant conductor of the Florida Symphonic Pops in Boca Raton, which became the Sunshine Pops Orchestra.
^McCall, Tris. "Sinatra at 100: Revisiting the voice of Hoboken", Inside Jersey, December 11, 2015. Accessed August 14, 2018. "On Watertown, a lost concept set about a small-town man abandoned by his wife, Sinatra collaborated with, among others, Four Seasons songwriter Bob Gaudio and arranger and pop bassist (and Newark Arts High graduate) Charles Calello."