Allmusic's Scott Yanow wrote, "Dizzy Gillespie's contributions to jazz were huge. One of the greatest jazz trumpeters of all time (some would say the best), Gillespie was such a complex player that his contemporaries ended up copying Miles Davis and Fats Navarro instead, and it was not until Jon Faddis's emergence in the 1970s that Dizzy's style was successfully recreated . . . Arguably Gillespie is remembered, by both critics and fans alike, as one of the greatest jazz trumpeters of all time."

Gillespie was a trumpet virtuoso and improviser, building on the virtuoso style of Roy Eldridge but adding layers of harmonic complexity previously unknown in jazz. His beret and horn-rimmed spectacles, his scat singing, his bent horn, pouched cheeks and his light-hearted personality were essential in popularizing bebop.

In the 1940s Gillespie, together with Charlie Parker, became a major figure in the development of bebop and modern jazz. He taught and influenced many other musicians, including trumpeters Miles Davis, Fats Navarro, Clifford Brown, Arturo Sandoval, Lee Morgan, Jon Faddis and Chuck Mangione.

Gillespie was born in Cheraw, South Carolina, the youngest of nine children of James and Lottie Gillespie. James was a local bandleader, so instruments were made available to Dizzy. He started to play the piano at the age of four. Gillespie's father died when the boy was only ten years old. Gillespie taught himself how to play the trombone as well as the trumpet by the age of twelve. From the night he heard his idol, Roy Eldridge, play on the radio, he dreamed of becoming a jazz musician. He received a music scholarship to the Laurinburg Institute in Laurinburg, North Carolina, which he attended for two years before accompanying his family when they moved to Philadelphia.

Gillespie's first professional job was with the Frank Fairfax Orchestra in 1935, after which he joined the respective orchestras of Edgar Hayes and Teddy Hill, essentially replacing Roy Eldridge as first trumpet in 1937. Teddy Hill’s band was where Gillespie made his first recording, "King Porter Stomp". At this time, Dizzy met a young woman named Lorraine from the Apollo Theatre, whom he married in 1940. They remained married until his death in 1993. Dizzy stayed with Teddy Hill’s band for a year, then left and free-lanced with numerous other bands. In 1939, Gillespie joined Cab Calloway's orchestra, with which he recorded one of his earliest compositions, the instrumental "Pickin' the Cabbage", in 1940. (Originally released on Paradiddle, a 78rpm backed with a co-composition with Cozy Cole, Calloway's drummer at the time, on the Vocalion label, No. 5467).

Dizzy was fired by Calloway in late 1941, after a notorious altercation between the two. The incident is recounted by Gillespie, along with fellow Calloway band members Milt Hinton and Jonah Jones, in Jean Bach's 1997 film, The Spitball Story. Calloway did not approve of Gillespie's mischievous humor, nor of his adventuresome approach to soloing; according to Jones, Calloway referred to it as “Chinese music”. During one performance, Calloway saw a spitball land on the stage, and accused Gillespie of having thrown it. Dizzy denied it, and the ensuing argument led to Calloway striking Gillespie, who then pulled out a switchblade knife and charged Calloway. The two were separated by other band members, during which scuffle Calloway was cut on the hand.

During his time in Calloway's band, Gillespie started writing big band music for bandleaders like Woody Herman and Jimmy Dorsey. He then freelanced with a few bands – most notably Ella Fitzgerald's orchestra, composed of members of the late Chick Webb's band, in 1942.

In 1943, Gillespie joined the Earl Hines band. Composer Gunther Schuller said:

Gillespie said of the Hines band, "People talk about the Hines band being 'the incubator of bop' and the leading exponents of that music ended up in the Hines band. But people also have the erroneous impression that the music was new. It was not. The music evolved from what went before. It was the same basic music. The difference was in how you got from here to here to here ... naturally each age has got its own shit".

Next, Gillespie joined Billy Eckstine's (Earl Hines' long-time collaborator) big band and it was as a member of Eckstine's band that he was reunited with Charlie Parker, a fellow member of Hines's band. In 1945, Gillespie left Eckstine's band because he wanted to play with a small combo. A "small combo" typically comprised no more than five musicians, playing the trumpet, saxophone, piano, bass and drums.

Bebop was known as the first modern jazz style. However, it was unpopular in the beginning and was not viewed as positively as swing music was. Bebop was seen as an outgrowth of swing, not a revolution. Swing introduced a diversity of new musicians in the bebop era like Charlie Parker, Thelonious Monk, Bud Powell, Kenny Clarke, Oscar Pettiford, and Gillespie. Through these musicians, a new vocabulary of musical phrases was created. With Charlie Parker, Gillespie jammed at famous jazz clubs like Minton's Playhouse and Monroe's Uptown House. Charlie Parker's system also held methods of adding chords to existing chord progressions and implying additional chords within the improvised lines.

Gillespie compositions like "Groovin' High", "Woody n' You" and "Salt Peanuts" sounded radically different, harmonically and rhythmically, from the swing music popular at the time. "A Night in Tunisia", written in 1942, while Gillespie was playing with Earl Hines' band, is noted for having a feature that is common in today's music, a non-walking bass line. The song also displays Afro-Cuban rhythms. One of their first (and greatest) small-group performances together was only issued in 2005: a concert in New York's Town Hall on June 22, 1945. Gillespie taught many of the young musicians on 52nd Street, including Miles Davis and Max Roach, about the new style of jazz. After a lengthy gig at Billy Berg's club in Los Angeles, which left most of the audience ambivalent or hostile towards the new music, the band broke up. Unlike Parker, who was content to play in small groups and be an occasional featured soloist in big bands, Gillespie aimed to lead a big band himself; his first, unsuccessful, attempt to do this was in 1945.

After his work with Parker, Gillespie led other small combos (including ones with Milt Jackson, John Coltrane, Lalo Schifrin, Ray Brown, Kenny Clarke, James Moody, J.J. Johnson, and Yusef Lateef) and finally put together his first successful big band. Gillespie and his band tried to popularize bop and make Gillespie a symbol of the new music. He also appeared frequently as a soloist with Norman Granz's Jazz at the Philharmonic. He also headlined the 1946 independently-produced musical revue film Jivin' in Be-Bop.

In 1948 Gillespie was involved in a traffic accident when the bicycle he was riding was bumped by an automobile. He was slightly injured, and found that he could no longer hit the B-flat above high C. He won the case, but the jury awarded him only $1000, in view of his high earnings up to that point.

In 1956 he organized a band to go on a State Department tour of the Middle East which was extremely well received internationally and earned him the nickname "the Ambassador of Jazz". During this time, he also continued to lead a big band that performed throughout the United States and featured musicians including Pee Wee Moore and others. This band recorded a live album at the 1957 Newport jazz festival that featured Mary Lou Williams as a guest artist on piano.

In the late 1940s, Gillespie was also involved in the movement called Afro-Cuban music, bringing Afro-Latin American music and elements to greater prominence in jazz and even pop music, particularly salsa. Afro-Cuban jazz is based on traditional Afro-Cuban rhythms. Gillespie was introduced to Chano Pozo in 1947 by Mario Bauza, a Latin jazz trumpet player. Chano Pozo became Gillespie's conga drummer for his band. Gillespie also worked with Mario Bauza in New York jazz clubs on 52nd Street and several famous dance clubs such as Palladium and the Apollo Theater in Harlem. They played together in the Chick Webb band and Cab Calloway's band, where Gillespie and Bauza became lifelong friends. Gillespie helped develop and mature the Afro-Cuban jazz style.

Afro-Cuban jazz was considered bebop-oriented, and some musicians classified it as a modern style. Afro-Cuban jazz was successful because it never decreased in popularity and it always attracted people to dance to its unique rhythms. Gillespie's most famous contributions to Afro-Cuban music are the compositions "Manteca" and "Tin Tin Deo" (both co-written with Chano Pozo); he was responsible for commissioning George Russell's "Cubano Be, Cubano Bop", which featured the great but ill-fated Cuban conga player, Chano Pozo. In 1977, Gillespie discovered Arturo Sandoval while researching music during a tour of Cuba.

His biographer Alyn Shipton quotes Don Waterhouse approvingly that Gillespie in the fifties "had begun to mellow into an amalgam of his entire jazz experience to form the basis of new classicism". Another opinion is that, unlike his contemporary Miles Davis, Gillespie essentially remained true to the bebop style for the rest of his career.

In 1960, he was inducted into the Down Beat magazine's Jazz Hall of Fame.

During the 1964 United States presidential campaign the artist, with tongue in cheek, put himself forward as an independent write-in candidate. He promised that if he were elected, the White House would be renamed "The Blues House," and a cabinet composed of Duke Ellington (Secretary of State), Miles Davis (Director of the CIA), Max Roach (Secretary of Defense), Charles Mingus (Secretary of Peace), Ray Charles (Librarian of Congress), Louis Armstrong (Secretary of Agriculture), Mary Lou Williams (Ambassador to the Vatican), Thelonious Monk (Travelling Ambassador) and Malcolm X (Attorney General). He said his running mate would be Phyllis Diller. Campaign buttons had been manufactured years ago by Gillespie's booking agency "for publicity, as a gag", but now proceeds from them went to benefit the Congress of Racial Equality, Southern Christian Leadership Conference and Martin Luther King, Jr.; in later years they became a collector's item. In 1971 Gillespie announced he would run again but withdrew before the election for reasons connected to the Bahá'í Faith.

Gillespie published his autobiography, To Be or Not to Bop, in 1979.

Gillespie was a vocal fixture in many of John Hubley and Faith Hubley's animated films, such as The Hole, The Hat, and Voyage to Next.

In the 1980s, Gillespie led the United Nation Orchestra. For three years Flora Purim toured with the Orchestra and she credits Gillespie with evolving her understanding of jazz after being in the field for over two decades. David Sánchez also toured with the group and was also greatly influenced by Gillespie. Both artists later were nominated for Grammy awards. Gillespie also had a guest appearance on The Cosby Show as well as Sesame Street and The Muppet Show.

In 1982, Gillespie had a cameo appearance on Stevie Wonder's hit "Do I Do". Gillespie's tone gradually faded in the last years in life, and his performances often focused more on his proteges such as Arturo Sandoval and Jon Faddis; his good-humoured comedic routines became more and more a part of his live act.

In 1988, Gillespie had worked with Canadian flautist and saxophonist Moe Koffman on their prestigious album Oo Pop a Da. He did fast scat vocals on the title track and a couple of the other tracks were played only on trumpet.

In 1989 Gillespie gave 300 performances in 27 countries, appeared in 100 U.S. cities in 31 states and the District of Columbia, headlined three television specials, performed with two symphonies, and recorded four albums. He was also crowned a traditional chief in Nigeria, received the Ordre des Arts et des Lettres; France's most prestigious cultural award. He was named Regent Professor by the University of California, and received his fourteenth honorary doctoral degree, this one from the Berklee College of Music. In addition, he was awarded the Grammy Lifetime Achievement Award the same year. The next year, at the Kennedy Center for the Performing Arts ceremonies celebrating the centennial of American jazz, Gillespie received the Kennedy Center Honors Award and the American Society of Composers, Authors, and Publishers Duke Ellington Award for 50 years of achievement as a composer, performer, and bandleader. In 1993 he received the Polar Music Prize in Sweden.

November 26, 1992 at Carnegie Hall in New York, following the Second Bahá'í World Congress was Gillespie's 75th birthday concert and his offering to the celebration of the centenary of the passing of Bahá'u'lláh. Gillespie was to appear at Carnegie Hall for the 33rd time. The line-up included: Jon Faddis, Marvin "Doc" Holladay, James Moody, Paquito D'Rivera, and the Mike Longo Trio with Ben Brown on bass and Mickey Roker on drums. But Gillespie didn't make it because he was in bed suffering from cancer of the pancreas. "But the musicians played their real hearts out for him, no doubt suspecting that he would not play again. Each musician gave tribute to their friend, this great soul and innovator in the world of jazz."

Gillespie also starred in a film called The Winter in Lisbon released in 2004. He has a star on the Hollywood Walk of Fame at 7057 Hollywood Boulevard in the Hollywood section of the City of Los Angeles. He is honored by the December 31, 2006 – A Jazz New Year's Eve: Freddy Cole & the Dizzy Gillespie All-Star Big Band at The John F. Kennedy Center for the Performing Arts.

A longtime resident of Englewood, New Jersey, he died of pancreatic cancer January 6, 1993, aged 75, and was buried in the Flushing Cemetery, Queens, New York. Mike Longo delivered a eulogy at his funeral. He was also with Gillespie on the night he died, along with Jon Faddis and a select few others.

At the time of his death, Gillespie was survived by his widow, Lorraine Willis Gillespie; a daughter, jazz singer Jeanie Bryson; and a grandson, Radji Birks Bryson-Barrett. Gillespie had two funerals. One was a Bahá'í funeral at his request, at which his closest friends and colleagues attended. The second was at the Cathedral of St. John the Divine in New York open to the public.

Gillespie, a Bahá'í since 1970, was one of the most famous adherents of the Bahá'í Faith which helped him make sense of his position in a succession of trumpeters as well as turning his life from knife-carrying roughneck to global citizen, and from alcohol to soul force, in the words of author Nat Hentoff, who knew Gillespie for forty years. He spoke about the Baha'i Faith frequently on his trips abroad. He is often called the Bahá'í Jazz Ambassador. He is honored with weekly jazz sessions at the New York Bahá'í Center in the memorial auditorium.

As a tribute to him, DJ Qualls' character in the 2002 American teen comedy film, The New Guy, was named Dizzy Gillespie Harrison.

Gillespie has been described as the "Sound of Surprise". The Rough Guide to Jazz describes his musical style:

In Gillespie's obituary, Peter Watrous describes his performance style:

Wynton Marsalis summed up Gillespie as a player and teacher:

Gillespie's trademark trumpet featured a bell which bent upward at a 45-degree angle rather than pointing straight ahead as in the conventional design. According to Gillespie's autobiography, this was originally the result of accidental damage caused by the dancers Stump and Stumpy falling onto it while it was on a trumpet stand on stage at Snookie's in Manhattan on January 6, 1953, during a birthday party for Gillespie's wife Lorraine. The constriction caused by the bending altered the tone of the instrument, and Gillespie liked the effect. He had the trumpet straightened out the next day, but he could not forget the tone. Gillespie sent a request to Martin Committee to make him a "bent" trumpet from a sketch produced by Lorraine, and from that time forward Gillespie played a trumpet with an upturned bell.

Gillespie's biographer Alyn Shipton writes that Gillespie probably got the idea for a bent trumpet when he saw a similar instrument in 1937 in Manchester, England, while on tour with the Teddy Hill Orchestra. According to this account (from British journalist Pat Brand) Gillespie was able to try out the horn and the experience led him, much later, to commission a similar horn for himself.

Whatever the origins of Gillespie's upswept trumpet, by June 1954, he was using a professionally manufactured horn of this design, and it was to become a visual trademark for him for the rest of his life. Such trumpets were made for him by Martin Committee (from 1954), King Musical Instruments (from 1972) and Renold Schilke (from 1982, a gift from Jon Faddis). Gillespie favored mouthpieces made by Al Cass. In December 1986 Gillespie gave the National Museum of American History his 1972 King "Silver Flair" trumpet with a Cass mouthpiece. In April 1995, Gillespie's Martin trumpet was auctioned at Christie's in New York City, along with instruments used by other famous musicians such as Coleman Hawkins, Jimi Hendrix and Elvis Presley. An image of Gillespie's trumpet was selected for the cover of the auction program. The battered instrument sold to Manhattan builder Jeffery Brown for $63,000, the proceeds benefiting jazz musicians suffering from cancer.

With Benny Carter

With CTI All Stars

With Duke Ellington

With Quincy Jones

With Gene Krupa and Buddy Rich

With Mike Longo

With the Manhattan Transfer

With Carmen McRae

With Charles Mingus

With Katie Bell Nubin

With Oscar Peterson

With Mongo Santamaria

With Woody Shaw

With Lillian Terry

With Randy Weston