Harold Ousley was born on January 23, 1929 in the Windy City of Chicago. Ousley was raised in the swing and hot jazz era, attending jazz performances at the Grand Terrace starting in elementary school (Ousley, 28). Ousley began his musical career in high school when his grandmother began giving him piano lessons in high school (Ousley, 103). Walter Dyat, who taught greats such as Nat King Cole and Gene Ammons, taught young Harold how to play the clarinet, and subsequently the saxophone. Ousley is a trained tenor saxophonist and self taught flautist, highly skilled in both jazz and blues performance styles. Ousley served as a background musician for famed musicians such as Count Basie, Dinah Washington and Billie Holiday (Ousley, 103). Although a sideman, Ousley is a veteran musician who dominated the 50’s Chicago jazz scene but never truly broke through to national stardom. In the 60’s and 70’s Ousley recorded singles with little major success. Ousley took to songwriting and at the age of 71, recored a singles record titled Grit-Gittin’ Feelin’. In this album, Ousley relies on soul jazz and hard bop to create earthy, melodic, call-and-response rhythms that underline jazz as a form of expression.

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Born in Chicago in October 1929, Norman Simmons is best known for his work as a pianist, arranger, composer and educator. During his musical career, Simmons worked with prominent jazz singers including Carmen McRae, Anita O'Day, and Joe Williams (Simmons 2007). Growing up in Chicago, Simmons was introduced to jazz at an early age. His teenage years were shaped by the influences of the “big band era,” and at the age of thirteen, Simmons began teaching himself to play music on his family piano (Merrill). Having had no formal lessons, Simmons learned to play piano by ear, listening to records of Duke Ellington and imitating his band on the piano. At the age of fourteen, Simmons began taking formal lessons at the Chicago School of Music (Simmons 2007). Simmons attended Wendell Phillips High School in Chicago, home to other prominent jazz musicians including Milt Hinton and Nat Cole. During that time, Simmons regularly made appearances at the local dance hall watching jazz stars such as Johnny Griffin and the Baby Band and Eugene Wright and the Dukes of Swing (Simmons 2007). As his talent on the piano quickly progressed, Simmons began playing a small role in gigs across Chicago before eventually earning a steady gig leading the house trio at one of Chicago's most popular jazz clubs, regularly opening for other artists on tour (Merrill). Simmons became a highly sought after accompanist and was persuaded to move to New York City in 1959. Following his move, Simmons began working with numerous jazz musicians making a career as an outstanding accompanist. Following his days as an accompanist, Simmons has continued to be an influence for other musicians having previously taught at Paterson State College in New Jersey (William Paterson University) and participating in the Jazzmobile program for 20 years (Merrill). The organization encourages music education at New York's public schools (Merrill). Simmons’ work both as an active musician and a teacher demonstrate his influence and passion to jazz music.