Dizzy Gillespsie’s contributions to jazz are similar to the mile markers on Route 1: both numerous and essential markers of the journey. From his early years, to his signature playing style, to the musical genres he both mastered and helped create, here’s a rundown of Gillespie’s creative contributions delivered Route 1 style: milestone by milestone.

Dizzy Gillespie’s Early Years

John Birks Gillespie was born on October 21, 1917 in Cheraw, South Carolina—right off Route 1—as the youngest of nine children. Thanks to his father, who was a part-time musician, Gillespie began learning to play the piano at the age of four, while also teaching himself the trombone. At age 12 he switched from the trombone to trumpet—the instrument that would go on to define most of his musical legacy. By the time he reached 15, Gillespie’s talent earned him a scholarship to the Laurinburg Institute, an African American preparatory school in North Carolina. For three years, Gillespie played the trumpet and piano, before dropping out to move to Philadelphia where his family had relocated.

Gillespie in Philadelphia and New York

Philadelphia held promise for aspiring musicians, and it wasn’t long before Gillespie was able to land his first gig in Frank Fairfax’s band. By 1937, he had switched to Teddy Hill’s orchestra, and by 1939, “Dizzy” (as his band members called him due to his goofball antics) had a tour of Europe under his belt. By that time he had also moved to New York, joining the orchestra of popular bandleader Cab Calloway. Gillespie used these years to develop his own distinctive playing style, with unscripted and experimental solos. But Gillespie’s style wasn’t for everyone—especially Calloway, who fired Gillespie after a spitball incident turned nasty.

Gillespie dedicated the next two years to circulating other bands while exploring and defining his musical style. Working in tandem with Charlie Parker, Gillespie began developing “bebop:” a fast-tempoed jazz style characterized by extended improvised solos and enabled by a virtuoso’s command of rhythm, scales, and advanced musical theory. Bebop departed from the jazz that came before by referencing the blues over big band dance music, and favoring riffs over structured melodies. While bebop didn’t immediately win everyone over, it became Gillespie’s calling card, helping catapult his career into the upper echelons of musical renown.

Dizzy Gillespie and the Rise of Bebop

By 1945, bebop had taken off and Gillespie found himself playing alongside Parker and other musicians in numerous jazz clubs around Harlem and Manhattan. Gillespie’s personal style evolved during this time as well. His dark sunglasses, beret, and carefully groomed goatee all became synonymous with bebop. A less imitable but just as iconic part of Gillespie’s look was his extremely puffed-out cheeks, which resembled a bullfrog’s every time he played. Gillespie cemented his signature look in 1953, when someone fell on his trumpet and bent the bell at a Manhattan club named Snookies. Gillespie liked the modification for the difference in tone made when he played. From then on out, he custom-designed his trumpets so that the bell turned upwards at a 45-degree angle.

Throughout every milestone, Gillespie performed and composed prolifically. By 1945, he was famous within the jazz circuit and was able to undertake many of the recordings that would help him cross over into the mainstream. Alongside Charlie Parker, Gillespie recorded the seminal bebop tracks “Salt Peanuts,” Shaw Nuff,” and “Groovin High.” Outside of performing and recording, Gillespie also attempted to lead a big band—an endeavor that flatlined after a Southern tour. Besides bebop, Gillespie also lent his innovation and talent to marrying jazz and Afro-Cuban music. It’s likely that several performers at the Ball and Chain Nightclub in Miami (also off Route 1) were inspired by Gillespie.

Gillespie’s Activism and Extracurriculars

Setbacks never put Dizzy off experimentation. The same creative forces that drove Dizzy to choose his unique musical style and fashion choices influenced other areas of his life as well. Beyond his career as a prolific jazz musician, Gillespie contributed his talents to both the political sphere and the Civil Rights Movement in one of the more unusual moments in U.S. history. The year 1956 saw the United States embedded in both the rising Civil Rights movement and Cold War tensions. The United States disliked the negative image connoted by many of the racial injustice stories that came out during that time, and wanted to present a more progressive global identity. At the same time, the pressures to act in response to the Cold War were also at an all-time high. These two factors led the United States to appoint Gillespie and his band as cultural ambassadors on a world tour through the Middle East, Pakistan, Syria, Turkey, and Greece. While Gillespie acknowledged the irony of the maneuver—noting that he was more welcome in some of these places than in his own country—it was a success, setting a precedent for the first time that the government provided economic aid in recognition of jazz, and encouraging similar initiatives in the future. As for Gillespie, it possibly influenced his decision to run for president in 1974 (a short-lived, if notable, enterprise). More likely, however, Gillespie’s presidential run came from the same inspiration by which he did voice-overs for animated films (one of which won an Academy Award).

Gillespie’s passion for music led him to continue playing well into the 1980s, making him one of the longest-performing jazz musicians of all time. He lived with his wife Lorraine in Englewood, New Jersey until he passed away in 1993.