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During his childhood, he received piano training. At 16, he performed piano in the Black Clan school orchestra. Later, he learned to play the trumpet. In 1940/41, he studied harmony and composition at the Bern Conservatory under Albert Moeschlinger. After finishing high school, he became second trumpeter in Fred Böhler's band. His music career was briefly interrupted by military service. Afterwards, he joined Jeo Grandjean's orchestra. From 1943, he returned to Fred Böhler's newly formed big band. The next year, he played first trumpet in saxophonist Eddie Brunner's band "Original Teddies," previously led by Teddy Stauffer.
That same year, he established his own professional jazz band. Soon after, the group expanded to a nine-piece orchestra featuring singer Kitty Ramon. In 1947, the ensemble grew to a 12-man big band and later to 16 members. In 1948, Osterwald founded the now legendary Hazy Osterwald sextet, which debuted at the "International Jazz Festival" in Paris alongside renowned artists like Charlie Parker. The original lineup included Ernst Höllerhagen (clarinet), Sunny Lang (bass), Gil Cuppini (drums), Pierre Cavalli (guitar), and Francis Burger (piano). Osterwald's sextet quickly gained international fame, partly due to their humorous stage performances, appearing in major European cities such as Stockholm and Lisbon. From 1954 onward, they also ventured into film.
The Hazy Osterwald sextet featured in the 1954 film "A Little Big Journey." Their major musical breakthrough in entertainment came in 1959 with the hit "Criminal Tango." The following year, Osterwald couldn't quite replicate this success with the Konjunktur Cha Cha, but had another hit with "Go with the Konjunktur," which referenced the economic boom, as well as with the 1960 title "Panoptikum." In 1961, the feature film "The Hazy Osterwald Story" was produced, starring Gustav Knuth, Eddie Arent, and Peer Schmidt, showcasing the band's rise. Early in the 1960s, television audiences enjoyed his own show. Osterwald toured with his sextet until 1979, during which time he renamed the band "Hazy Osterwald Jetset."
After a hiatus, he resumed performing jazz in 1984 under the name "Hazy Osterwald and the Entertainers." He played the vibraphone, a classic jazz percussion instrument. In 1984, he received the Prix Walo. The following year, he married actress Eleonore Mathilde Schmid, and they settled in Lucerne. In 1999, he published his autobiography titled "Criminal Tango." In 2009, he was honored with the Swiss Jazz Lifetime Achievement Award for his contributions to music.
