Jazz and the saxophone both entered the national consciousness around the end of World War I, and it was clear at that point that the two would have some kind of a future together. But for a few years, no one knew how that would happen.The first major musician to play jazz on the saxophone was Sidney Bechet, who treated the soprano instrument like a clarinet with a built-in megaphone. It remained for the founding generation of saxophonists – Frank Trumbauer, Jimmy Dorsey, Adrian Rollini, and especially Coleman Hawkins and Bud Freeman – to show what could be done with the instrument.

Freeman (1906-90), whose centennial is being celebrated this month with the reissue of one of his greatest albums, approached the horn in a unique manner. Before the saxophone entered the jazz universe, it was mainly known as a novelty device in vaudeville – it had as much in common with the unicycle as it did with the trumpet. Freeman’s innovation was to build on the trickster aspect of the horn, superimposing a jazz and blues rhythmic and tonal sensibility.

Freeman debuted his tour de force showstopper, “The Eel,” in 1933 in a session under the name of Eddie Condon, the bandleader he was associated with for most of their long careers. A winding melody that constantly doubled back on itself, full of carefully articulated 16th and 32nd note runs, “The Eel” was distinguished from other finger-busters of the era by the way Freeman swung. He had a distinct rhythmic mobility that allowed him to keep up with both the best black and white jazzmen of his day. He could play any standard tune with gusto and joie de vivre, and he could wail the blues.

Freeman, a native Chicagoan, fell in love with the saxophone at 14, when he heard a star saxophone soloist playing pretty tunes in a local cinema. It was the image of the instrument – this one happened to be diamond-studded – as much as the sound that seduced him. He began practicing on the now archaic C-melody saxophone around the time he began attending Austin High School, where he soon found himself at the center of a band of like-minded youngsters including cornetist Jimmy McPartland, drummer Davey Tough, clarinetist Frank Teschmacher, and Condon, the guitarist who would soon establish himself as their de facto leader.

They became intrigued by jazz upon hearing the New Orleans Rhythm Kings, and were irrevocably hooked by King Oliver’s Creole Jazz Band, particular Oliver’s cornet protege, the young Louis Armstrong. Inspired by Armstrong’s example, Freeman, Condon, and the others devoted their lives to playing New Orleans jazz. But they put a Chicago stamp on the music.

The Austin High gang began recording in 1927, becoming one of the first New Orleans-style ensembles to employ a tenor saxophone soloist. Freeman’s earliest solos on “Sugar” and “China Boy” are rough and throaty in the manner of such clarinetists as Teschmacher and Pee Wee Russell.

Along with the younger Benny Goodman, Freeman left Chicago later that year to travel to New York with bandleader Ben Pollack, formerly the drummer in the Rhythm Kings. He spent most of the ’30s touring with big bands: After playing alongside Pollack, he toured with the dance orchestras of Joe Haymes, Ray Noble,Tommy Dorsey, and Goodman. Beginning in 1938, he was a regular on producer Milt Gabler’s Commodore Records, coming off especially well on two 1938 trio sessions with pianist Jess Stacy and drummer George Wettling. In 1940, he led a band billed as his “Famous Chicagoans” in one of the great jazz recording dates of all time, sharing the spotlight with Russell and the trombonist and singer JackTeagarden.

For the next 50 years, Freeman was unstoppable. He continually toured the world with small groups, often as the bandleader. In his record dates, he generally participated in traditional Chicago-style projects involving the Condonites. One of the best of these has just been reissued for the first time in the United States, the 1957 “Chicago/Austin High School Jazz in Hi-Fi” on the new Mosaic Single series (MCD-1002).

Like many postwar sessions by the Chicagoans, it has the feeling of a reunion and brings together Teagarden, Russell, Wettling, McPartland, and trumpeter Billy Butterfield. There is outstanding ensemble work on tunes that these men had recorded before, such as the Rhythm Kings’ wailing “Prince of Wails” and Teagarden’s blues “Jack Hits the Road.” The album also features four bonus tracks, of which “I Cover the Waterfront” is a trombone and vocal feature for Teagarden. “Sunday” and “You Took Advantage of Me,” are Condon-esque jam sessions that, like the best music in the Chicago genre, sound relaxed and driving at the same time. The fourth tune, “The Reverend’s in Town,” is something else again; instead of featuring the expected, Dixieland-style polyphony, it uses the streamlined, smoother style of swing and modern harmonizing.

Also recently reissued is the 1958 “Tiger Rag and All That Jazz” (Mighty Quinn 1105), Condon’s only album for World Pacific. The repertory is mostly from the Original Dixieland Jazz Band, and the date is sparked by cornetist Rex Stewart. Freeman is particularly animated and aggressive on “Livery Stable Blues,” the ODJB classic that had begun life as animal imitation novelty. It’s a great album of Chicago jazz that shows that these men were hardly standing still, even though they were still playing the same songs in the same company.

Indeed, Freeman did a 1945 album for Capitol with guitarist Carl Kress that was much more in the up-to-date swing style, and in 1962 he teamed with two guitarists, Kress and George Barnes, in a most unusual trio. In 1960, on “All Star Swing Sessions,” Freeman recorded a blues march (“March On”) that in retrospect sounds very similar to what Art Blakey and the Jazz Messengers were doing at the time. In 1980 he recorded the album, “The Dolphin Has a Message,” in a quasi-modal style with the modern British pianist Brian Lemon. Freeman cut his last known session in the Netherlands in 1986, 60 years after his first Chicago date. His was a remarkable legacy, making sure that no one had to go and reinvent the eel.

wfriedwald@nysun.com