Friday, October 13, 2023

Profiles In Coolness: Dizzy Gillespie: Iconic Jazz Legend


Culture—in its truest definition—is acquainting ourselves with the best the world has ever known. It doesn't matter whether we are talking about motorcycles, ballet, or clothing design. Every genre begins with a bell curve of sorts that begins with a genesis point and then hits an apex or zenith point. Some curves descent quickly while others just keep going straight for a long time. Take Rolex for example. Rolex's genesis point occurred when founder, Hans Wilsdorf thought it made much more sense for people to wear watches on their wrist than on a chain in a vest pocket. So he took disruptive action and began climbing his bell curve from the early 1900s, through the introduction of Rolex Oyster in 1926, and the Rolex perpetual in 1931, up to the Datejust in 1945, and onward to the Submariner and GMT-Master in 1953 and 1955. Also in 1955 came the Rolex Day-Date. The 1950s were the Golden Age for Rolex, in which they hit their zenith...

Jazz, like the Blues, Rock & Roll and Rap, all began as uniquely African-American musical art-forms. This story chronicles the man who was perhaps the greatest jazz pioneer, or certainly one of them—Dizzy Gillespie...

What is cooler than sitting in a beautiful Italianate coffee shop, listening to some very cool live Jazz or vintage Jazz?  Understanding Jazz is like understanding how mechanical watches work. Jazz music is kind of like classical music, in the sense, it is not only an acquired taste but can also be challenging to understand, due to the fact it can be confusing, complex, esoteric and even arcane. To my way of thinking, vintage Jazz in many ways has the same appeal as vintage Rolex watches. They are both timeless in appeal, beautiful in design and iconically outstanding at the same time.

In this amazing story, I try, as best as I am able, to not only share Dizzy Gillespie's amazing history so you can understand what made him tick, and at the same time offer a high-level overview of some great early American Jazz history. It has been said Rolex Tells History, and When a man has a world in his hands, you expect to find a Rolex on his wrist. This is an amazing example of exactly let's hop in the Rolex time-machine and travel back in time on a magnificent Jazz journey through history...

...Rolex Ultra-Super-Coolness...

Dizzy Gillespie


Iconic Jazz Legend & Trumpet Virtuoso 

The King of BeBop

An Amazing Career with a Rolex GMT Keeping His Time

In the past, I have published a number of profiles in my Rolex Coolness Series, and they included Paul Newman Dr. Martin Luther King Jr. Steve McQueen, Miles Davis and Robert Redford.  Dizzy Gillispie came before all of them and maybe the coolest...

Dizzy Gillespie was born John Birks "Dizzy" Gillespie, on October 21, 1917, in Cheraw, South Carolina. Dizzy Gillespie is known by many titles including the King of BeBop, and he is considered to be one of the primary architects of modern jazz as well as being one of the greatest jazz trumpeters of all time, and he wore a Bakelite Pepsi Rolex GMT-Master with no crown guard on a Jubilee Bracelet, for at least 35 years from at least 1958 until he died in 1993. The photo below shows the artwork cover of his seminal 1961 record album titled "An Electrifying Evening With The Dizzy Gillespie Quintet." Notice Dizzy is wearing his Pepsi GMT on the album cover.

"I've worn my Rolex GMT-Master for 30 years. That's the thing with Rolex; they last forever. " –Dizzy Gillespie (1987)

Dizzy Gillespie Pictured Above in 1961 Wearing His Trademark Rolex GMT Master

You can see Dizzy Gillespie's Pepsi Rolex GMT-Master on his wrist in the photos above and below that were taken in 1961, and of course, it stands to reason he preferred a Rolex GMT-Master because he regularly traveled all over the world.

Dizzy Gillespie is pictured below in 1961 sporting his Pepsi GMT-Master on a Jubilee bracelet. Dizzy Gillespie is considered to be one of the founding fathers of Be-Bop and Afro-Cuban Jazz. If you think about it, people really define themselves by their choice in the wristwatch they wear, so it is fascinating Dizzy chose to do so with a Rolex GMT-Master.

Dizzy Gillespie Pictured Above in 1961 Wearing His Trademark Rolex GMT Master

Dizzy Gillespie is pictured below with fellow Jazz legend John Coltrane in 1961 backstage at the Olympia in Paris, and you can see Dizzy's Rolex Jubilee bracelet. 

Dizzy Gillespie Pictured Above in 1961 Wearing His Trademark Rolex GMT Master

In the photos above we see Dizzy Gillespie wearing his Rolex GMT on a Rolex Jubilee bracelet, and in the two photos below, which were taken by Ted Williams, you can see Dizzy wearing a Rolex GMT on an Oyster Bracelet.

The End Of World War II

The Birth Of Modern Jazz

On May 5, 1945, the Nazi leader, Hermann Göring, who was Hitler's second in command surrendered to the United States, and Europe was free again. 

America made it through World War II listening to Orchestral Golden Age Period Big Bands that were headed by famous bandleaders like Artie Shaw, Louis Armstrong, Glen Miller, Benny Goodman, Cab Calloway, Earl Hines, Duke Ellington, Guy Lombardo, Tomey Dorsey, Lawrence Welk, and Count Basie. Big bands were focused more on the bandleader, and not so much on iconic individual virtuoso musicians.

Due to the war effort in America, jazz had not evolved past swing and the Big Bands, but modern jazz forces were brewing in the United States from around 1942.

On June 22, 1945, in the New York City Town Hall, a tipping-point event took place which is considered to be the birth of modern Jazz.

Pictured below on stage at that seminal 1945 jazz event were Charlie "Bird" Parker playing saxophone,  Dizzy "Diz" Gillespie playing trumpet,  Max Roach on drums, Don Byas on saxophone, "Big Sid Cattlet" on drums, Al Haig on Paino, and Curley Russell on bass. The revolutionary new jazz known as Bebop was born that day. 

A few months after the photo above was taken, on September 2, 1945, the Japanese officially surrendered to the United States. World War II was now over and anything seemed possible...

Big Band orchestral music with its Swing Era music was very popular in the United States from 1935 to 1946. Swing era bands consisted of 'Big' Bands of up to fourteen pieces playing in an ensemble-based manner. Swing was primarily for dancing and it gave way to the BeBop sound, which was more for listening enjoyment. BeBop bands were much smaller than big bands and consisted primarliy of rhythm sections with an expanded role that incroporated alto and tenor saxaphone, piano, dobule bass, trumpet and drums. 

BeBop had a more intellectual sound that consisted of fast tempo and frenetic jazz style that involved complex harmony and rhythm coupled with quickly changing chord progressions that would often change key. This new style of improvisational Jazz showcased jazz musicians desire to be accepted as virtuoso artists and soloists that were masters of their instruments. Bebop was exploratory Jazz that often involved complex syncopation, asymmetrical phrasing, and fast tempo. With the advent of Beboop, arranged Swing Era jazz music was on its way out with improvisational music largely replacing it.

Jazz Man, Take My Blues Away

Dizzy Gillespie is pictured below on May 1, 1947, in New York. In many ways, he was the archetype of an Avant-garde hipster, cool-cat, as we see with his beret, goatee, and stylish glasses.

"When I found the trumpet, I found the best part of me."–Dizzy Gillespie

Dizzy Gillespie is pictured below with his wife in New York in May of 1946. They are located on the corner of West 52nd Street and Avenue Of The Americas.

Dizzy Gillespie is pictured below on May 1, 1947 in New York , as he writes the phrase "Be-Bop" on a black board.

In the two photos below taken by William Gottlieb, we see Dizzy Gillespie watching Ella Fitzgerald in absolute awe as she sings at the Downbeat Club in New York in September of 1947. Ella Fitzgerald probably had the prettiest female voice in the history of singing. Ella Fitzgerald also wore Rolex watches in her lifetime. We also see Jazz legend Milt Jackson in the photo.

"Jazz is a joyful music. That's why I love it so!"–Dizzy Gillespie

Speaking of the magic of Ella Fitzgerald, the seminal photo below was taken by Herman Leonard in 1948 in a New York club and shows Jazz legends Duke Ellington and Benny Goodman, both in complete awe as they witness Ella singing...

Charlie Parker & Dizzy Gillespie

Charlie Parker was born in Kansas City, Kansas on August 29, 1920, and he was referred to by his cool hepcat friends simply as "Bird." Bird was a radical saxophone player and composer. Charlie Parker was the leading figure in the development of the Bebop jazz movement, which was characterized by improvisation, and fast-moving tempo, coupled with expert mastery of the saxophone.

In 1942, Charlie Parker met Dizzy Gillespie (pictured below) and "Bird" and "Diz" became best friends. Charlie Parker spent a lot of time playing gigs in Harlem with other young iconoclasts, and he became friends with many other future jazz legends, including Thelonius Monk and Miles Davis.

Charlie Parker was recognized as an icon for the hipster subculture that existed in the United States and in France in the 1940s and 1950s. Charlie Parker played the music he liked and was the personification of an artist unwilling to compromise his belief system, as he refused to go along with the status quo. When Bird was young, he practiced for 4 years, playing up to 15 hours a day, and as a result, developed his highly improvisational playing style.

When Bird was a young man, he was in an automobile accident and the doctor treated him with morphine, and he became addicted, and later developed an addiction to heroin, which ultimately killed him. Charlie Parker moved to New York City in 1939 in order to be in the capital of American Jazz. 

In this next photo taken in the Downbeat club in New York in 1947, we see Charlie Parker, sitting with Red Rodney watching Dizzy Gillespie play his trumpet (seen in the mirror) in complete awe. Modern Jazz, known at the time as BeBop was being born. 

It is worth noting the social impact early jazz music had on race relations in the United States. It was common for whites and blacks, who would seemingly have little in common in their daily lives, to come together at a jazz club late-night in New York and be best of friends. Of course, on some levels, this was a hypocrisy, but at the same time jazz helped build a bridge for Americans which improved race relations.

This is important to contextualize because if you did not live through this horrible chapter in human behavior it is not easy to understand. Imagine for a moment, no matter what color your skin is today, what it would be like to live in a world where you are not legally allowed to use the same bathrooms, or able to eat in the same restaurant as somebody else just because their skin is a different shade than yours? Yet, all of the top jazz musicians had to live through this complete absurdity, and as a human being, it stands testament to the real strength of the human soul, in the sense they could live through those challenges, and still innovate like crazy!

The Bebop movement to a certain extent came about because many black jazz musicians felt that white band leaders had usurped their jazz music and profited heavily from swing music. Fellow jazz musician and iconoclast, Theolonius Monk is pictured below on the left with Dizzy Gillespie in 1963 at the Monterey Jazz Festival. Monk was once quoted as saying: "We wanted a music they couldn't play."

1946 Dizzy Gillespie Jivin' In Be Bop

Dizzy Gillespie began his career in Cab Calloway's swing band. Cab Calloway fired Dizzy from his big band and said: "He was good, but sometimes he was so wild, he sounded dizzy." In the next video, we see Dizzy Gillespie, conducting his own big band, which included Milt Jackson.

Dizzy Gillespie is pictured below performing in New York at the Royal Roost in 1948.

In this next photo, taken in 1948, we see the legendary singer, Mel Torme with model June Bright watching Dizzy Gillespie in complete delight live in a Hollywood nightclub. This is such a cool photo as we see Dizzy's reflection in the mirror behind Mel and June's head.

In this next photo taken in 1948 we see Dizzy Gillespie signing his autograph for three teenage girls who are wearing blue jeans, berets, horn rimmed glasses and goatees mimicking the King of Bebop. 

Charlie Parker & Dizzy Gillespie in 1952

Fellow trumpeter Miles Davis once said, "You can tell the history of Jazz in four words, Louis Armstrong, Charlie Parker." In the video below we witness Dizzy Gillespie jamming with Charlie "Bird" Parker. Despite being a jazz legend, Charlie Parker would be dead only three short years later at the young age of 34.

Dizzy met Charlie Parker when Dizzy was in Cab Calloway's band. After hours, Dizzy would travel uptown in New York, to go and play with Charlie Parker late-night is Jazz clubs. Together the two jazz virtuosos would experiment like crazy, and improvise with new techniques. People danced swing to Big Band jazz, with this new form of modern Jazz, people would not dance, but listen. This was the birth of Modern Jazz, A.K.A., "The New Jazz."

The cool Hepcat/Hipster subculture, and later the Beat Generation perceived Charlie Parker not as an entertainer, but as an intellectual artist who refused to compromise and go along with the status quo. Bird was hip—not square.

 Dizzy Gillespie & Miles Davis in 1952

Dizzy Gillespie and Miles Davis both started performing and recording with Charlie Parker in 1945, and we see Dizzy Gillespie playing trumpet side by side with Miles Davis in 1952. Dizzy was 9 years older than Miles.

Miles Davis is pictured below, and despite the fact he and Dizzy Gillespie were only nine years apart, they were would evolve musically in divergent directions—while both wearing Rolex watches.

Dizzy Gillespie is pictured below with Miles Davis, working on a composition in Paris, France in 1958.

In 1956, Dizzy Gillespie became the worlds first formal Jazz ambassador when the State Department sent him on the worlds first world Jazz tour. If you look closely at the photo above you see Dizzy Gillespie hanging out with Miles Davis, and notice Dizzy is wearing his trademark Pepsi Rolex GMT-Master.

1958 Monterey Jazz Festival
The First Rolex Sports Watch In The Jazz World

Dizzy Gillespie is pictured below practicing on his trumpet at the 1958 Monterey Jazz Festival, and notice he is wearing his trademark Rolex GMT-Master. This is the earliest known photo I am aware of Dizzy Gillespie wearing his Rolex GMT Master, and the most profound fact is that the GMT-master had only been available on the market for 3 years in 1958, since Rolex introduced it at BaselWorld in Geneva in 1955! 

Dizzy Gillespie Pictured Above in 1958 Wearing His Trademark Rolex GMT Master

Now that I think about it, I believe this is the earliest known photo of anybody I have ever seen wearing a Rolex GMT-Master!!! It certainly pre-dates Sean Connery wearing a Rolex Submariner in 1962 in Dr. No. I think the only image I have ever seen of a man wearing a sports Rolex prior to when this photo was taken, is Jacques-Yves Cousteau, when he was testing Rolex Submariner prototypes for Rolex in 1953, and that was only five years earlier!!! I think this fact likely makes Dizzy the coolest cat that ever wore a GMT-Master!!! 

Also, it is likely Rolex gave Jacques Cousteau the prototype Rolex watches to test, whereas, my best guess is that Dizzy likely purchased his GMT-Master. This makes Dizzy the first true civilian I am aware of to be photographed in history wearing a Rolex sports watch!!! The Rolex GMT-Master ad seen below is from 1958, which would be the same model Dizzy Gillespie wore...You can learn much more about the GMT-Master by reading my story named "The Complete History Of The Rolex GMT-Master."

Dizzy Gillespie was one of the founding musicians of the Monterey Jazz Festival, along with Billy Holiday, Louis Armstrong, Milt Jackson, Sonny Rollins and Dave Brubeck. I can't believe I am looking at a photo of Dizzy at the first Monterey Jazz Festival, and he is sporting his Rolex GMT!!! Of course, the Monterey Jazz Festival still exists today, and it is one of the longest consecutively running Jazz festivals in the world.

Dizzy Gillespie worshiped Louis Armstrong, and in the photo taken below on October 1, 1958 at the Monterey Film Festival, we see Dizzy Gillespie kissing Louis Armstrong's hand. If you are not familiar with Louis Armstong, you should be. He was not only the father of Jazz, but the greatest Jazz musician and singer that ever lived.

Dizzy Gillespie is featured below in 1959 playing with Louis Armstrong on The Jackie Gleason Show playing Umbrella Man. Louis Armstrong and Dizzy Gillespie are considered to be the two greatest trumpet players in history. Dizzy was not only a radical trumpeter, but also an amazing scat singer. Watching this video is mind-boggling. It is the best of Old School Jazz succession "Satchmo" embracing "Dizzy" New School Jazz.

When The Saints Go Marching In
Exploring The Wonderful World Of Louis Armstrong

As I previously mentioned, Louis "Satchmo" Armstrong was "THE" Jazzman. What made him "THE" Jazzman? He was simply the greatest Jazz singer, musician and trumpeter who ever lived, and to see why, watch the amazing videos below. It has been said that old Satchmo was Gabriel's First Assistant ;-)

Louis Armstrong also had, what in my opinion is probably the most genuinely beautiful and sincere, happy smile–I have ever seen. When Satchmo smiled, his face lit up like a Christmas tree, and I love his absolute optimism!!! In this first video we see Satchmo singing with the beautiful and talented Jewel Brown. 

"The bottom line of any country in the world is 'What did we contribute to the world?', and we contributed Louis Armstrong." –Tony Bennett

"You can tell the history of jazz in four words, Louis Armstrong; Charlie Parker." –Miles Davis

Croon A Tune
From The Heart Of Dixie

In this next video we see Louis Armstrong singing a Dixie Medley with Dean Martin on the Dean Martin show, and we see Dino and Satchmo at the absolute top of their games. This video is just amazing!!!

What A Wonderful World is featured below, and it is arguably Louis Armstrong's best known and most famous song. I believe, What A Wonderful World, is a genuine reflection of his perspective on mankind, and the earth we all share. 

On a personal note, I will share an interesting detail with you... When I came up with the slogan for Jake's Rolex World, ten years ago, I decided on "Exploring The Wonderful World Of Rolex", and it does not take much imagination to understand where this came from.

"If anybody was Mr. Jazz it was Louis Armstrong. He was the epitome of jazz and always will be. He is what I call an American standard, and American original." –Duke Ellington

"My whole life has been happiness. Through all the misfortunes...I did not plan anything. Life was there for me, and I accepted it. And life, whatever came out, has been beautiful to me and I love everybody." –Louis Armstrong

If you are a regular reader of Jake's Rolex World, you know I tend to always wander off the reservation, and extrapolate like crazy with fascinating segways. In this case I just couldn't resist with sharing the Satchmo videos. I did this as there is no real discussion on jazz history without deferring to Louis Armstrong, and Satchmo was—and still is—an international treasure, that belongs to the ages.

This last video from the "High Society Picture", as Satchmo referred to it, really showcases Louis Armstrong's trumpet and singing skills, along with Bing Crosby. Hey Pop's, you wanna grab a little of what's left here? Ya Daddy, Yeah!!!

"Louis Armstrong is the beginning and the end of music in America." –Bing Crosby

In this next video we see Louis Armstrong and Dizzy Gillespie talking about their appreciation for each other in 1970. Dizzy's performance and speech was given at the Newport Jazz Festival in 1970, not so long before Louis Armstrong passed away, and notice Dizzy is wearing his trademark Rolex GMT-Master.

In the photo below we see a photo of Miles Davis meeting Louis Armstrong, and you can see the genuine awe in Miles Davis's eyes, and if you know much about Miles Davis, he didn't look at anybody else like this.

“You can’t play nothing on modern trumpet that doesn’t come from Louis Armstrong, not even modern shit. I can’t even remember a time when he sounded bad playing the trumpet. Never. Not even one time. He had great feeling up in his playing and he always played on the beat. I just loved the way he played and sang.” –Miles Davis

 Now back to our regularly scheduled programming ;-)

Dizzy On The French Riviera

In the next photo below, we see Dizzy Gillespie playing his trumpet in the water on the French Riviera in 1960, and notice he is wearing his Rolex GMT Master on his Oyster Bracelet!

In the photo below we see Dizzy Gillespie playing in an intimate jazz club in 1964, and you can see him wearing his Rolex GMT-Master on a Jubilee bracelet.

This next video was filmed at the Olympia theater in Paris France in 1965 and it features The Dizzy Gillespie Quintet performing One Note Samba.

Next up we see The Dizzy Gillespie Quintet in 1966, playing on the BBC Jazz 625 Show, and he is wearing his trademark Rolex GMT-Master. This performance really shows how much Dizzy's jazz style evolved and became smoother and more refined. In the mid 1960s his music gained more of a congo/samba-like, almost mellow, or melancholy vibe. I hesitated to use the words, "melancholy" since Diz's music is so energetic, sharp and vibrant.

Dick Cavett Interviews Dizzy Gillespie in 1982

A Night In Havana with Dizzy Gillespie

Dizzy Gillespie was not only the king of Bebop jazz but he was really into Afro-Cubano Jazz, and in 1989 he starred in this amazing documentary on his performance at the Fifth International Jazz Festival, in Havana, Cuba. In the video it shows Dizzy Gillespie hanging out with Fidel Castro in Cuba, who, by the way, took Cuba wearing a Rolex GMT-Master.

Dizzy Gillespie Pictured Above in 1989 Wearing His Trademark Rolex GMT Master

Dizzy Gillespie is pictured below with First Lady and President Bush on November 17, 1989, at a White House ceremony where Dizzy received the National Medal Of Honor.

Dizzy Gillespie is pictured below in the late 1980s, and he is still wearing his trademark Rolex GMT Master. The history of Jazzy Trumpeters can really be broken up into a succession of five generations, with each having a man who best symbolized it. The first was Louis Armstrong; then Dizzy Gillespie; then Miles Davis; then Wynton Marsalis, and most recently Chris Botti.

Dizzy Gillespie was a teacher of Wynton Marsalis who summed up his thoughts on Dizzy, when he said:

"Dizzy Gillespie's playing showcases the importance of intelligence. His rhythmic sophistication was unequaled. He was a master of harmony—and fascinated with studying it. He took in all the music of his youth—from Roy Eldridge to Duke Ellington—and developed a unique style built on complex rhythm and harmony balanced by wit. Gillespie was so quick-minded, he could create an endless flow of ideas at unusually fast tempo. Nobody had ever even considered playing a trumpet that way, let alone had actually tried. All the musicians respected him because, in addition to outplaying everyone, he knew so much and was so generous with that knowledge..." –Wynton Marsalis