Serge Chaloff (November 24, 1923 – July 16, 1957) was an American jazz baritone saxophonist. One of bebop's earliest baritone saxophonists, Chaloff has been described as 'the most expressive and openly emotive baritone saxophonist jazz has ever witnessed' with a tone varying 'between a light but almost inaudible whisper to a great sonorous shout with the widest but most incredibly moving of vibratos.'

Serge Chaloff was the son of the pianist and composer Julius Chaloff and the leading Boston piano teacher, Margaret Chaloff (known professionally as Madame Chaloff). He learned the piano from the age of six and also had clarinet lessons with Manuel Valerio of the Boston Symphony Orchestra. At the age of twelve, after hearing Harry Carney, Duke Ellington's baritonist, he taught himself to play the baritone. Chaloff later explained to Leonard Feather in an interview: 'Who could teach me? I couldn't chase [Harry] Carney around the country.'

Although he was inspired by Carney and Jack Washington, Count Basie's baritone player, Chaloff did not imitate them. According to his brother, Richard, 'he could play (baritone) like a tenor sax. The only time you knew it was a baritone was when he took it down low. He played it high....He had finger dexterity, I used to watch him, you couldn't believe the speed he played. He was precise. He was a perfectionist. He would be up in his bedroom as a teenager. He would be up by the hour to one, two, three in the morning and I'm trying to sleep and he'd go over a phrase or a piece until it was perfect...I used to put the pillow over my head, we had battles.'

From the age of fourteen, Chaloff, was sitting in at Izzy Ort's Bar & Grille a famous live music venue on Essex Street in Boston. Richard Chaloff remembered: 'He didn't have a permit to work but he was pretty tall and he went down to see Izzy Ort...and played for him and Izzy liked the sax...and he hired my brother to work nights....My mother used to pray on Sundays that that he'd make it outa there....My brother sat in with bandsmen that were in their thirties and forties...and here he was fourteen, fifteen years old and he played right along with them, and he did so well that they kept him.'

In 1939, aged just sixteen, Chaloff joined the Tommy Reynolds band, playing tenor sax. This was followed by jobs in the bands of Dick Rogers, Shep Fields and Ina Ray Hutton. In July 1944, he joined Boyd Raeburn's short-lived big band, where he played alongside Dizzy Gillespie and Al Cohn, who became a lifelong friend. With Boyd Raeburn, in January 1945, he made his first recordings, including 'Interlude' (Dizzy Gillespie's 'A Night in Tunisia'), where his baritone can be heard in the opening section of the song.

While with Boyd Raeburn, Chaloff first heard Charlie Parker, who became his major stylistic influence. Stuart Nicholson argues that, rather than imitating Parker, Chaloff was inspired by his example 'grasping more the emotional basis for Parker's playing and using it as a starting point for his own style.' Richard Chaloff said that his brother 'palled' with (Parker) in New York. Any time he had the chance he would pal with him. He would sit in with him at night....My brother used to say that he was up till 4,5,6, in the morning with the Bird.....All the beboppers found each other out'

Alongside his 1945-1946 work in big bands led by Georgie Auld and Jimmy Dorsey, Chaloff performed and recorded with several small bebop groups, 1946-1947. These included Sonny Berman's' Big Eight, Bill Harris's Big Eight, the Ralph Burns Quintet, Red Rodney's Be-Boppers, and his own Serge Chaloff Sextette, which released two 78 records on the Savoy label. Three of the four tunes recorded were written and arranged by Chaloff while the fourth, 'Gabardine and Serge', was by Tiny Kahn. 'All four tunes are daredevil cute and blisteringly fast,' wrote Marc Myers. 'They showcase tight unison lines and standout solos by four of the six musicians, who are in superb form....(On 'Pumpernickel') Chaloff shows off his inexhaustible and leonine approach to the baritone sax.'

Serge Chaloff became a household name in 1947, when he joined Woody Herman's Second Herd. This was known as the 'Four Brothers Band', after the reed section, comprising Chaloff, Stan Getz, Zoot Sims, Herbie Steward, and a little later Al Cohn. He was featured on many Herman recordings, including "Four Brothers", Keen and Peachy", and had solo features in Al Cohn's "The Goof and I". and "Man, Don't Be Ridiculous." On the latter, he demonstrated 'an astonishing technical facility that was quite without precedent on the instrument.'