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Does Miles Ahead Deserve an Oscar?


View From The Inside

By Randy Freedman


Miles Dewey Davis III was a trumpeter, bandleader and composer. The great jazz musician was born on May 26, 1926 in Alton, Ill. In 1944, he moved to New York and studied music at Juilliard, eventually leaving to join other greats like Charlie Parker, Thelonius Monk and Charles Mingus on the nightclub circuit.

Davis is regarded as one of the most acclaimed and influential figures in the history of jazz, and all 20th century music. Ever-changing in directions, Davis was at the forefront of a number of major stylistic developments in this genre over his five-decade-long career.

Miles Ahead is a 2016 feature film directed by and stars Don Cheadle, representing a few days in the life of Davis during the later stages of his career.

Davis came from an affluent family that encouraged his musical pursuits, but also wanted him to receive a strong traditional education. His father, Miles Dewey Davis, Jr., was a dentist. In 1927, the family moved to East St. Louis. They also owned a substantial ranch near Pine Bluff, Ark., where Davis’ father and grandfather were from. It was both in East St. Louis and near Pine Bluff that young Davis developed his appreciation for music, listening to the gospel music of the black church.

Davis’ mother, Cleota Mae Davis, wanted her son to learn the piano. Cleota was a capable blues pianist herself, but she did not let Miles know it. His musical studies began at 13 when his father gave him a trumpet and arranged lessons with a local musician, Elwood Buchanan. Davis later suggested that his father’s instrument choice was made largely to irk Miles’ mother, who disliked the trumpet’s sound.

Against the fashion of the time, Buchanan stressed the importance of playing without vibrato; he was reported to have slapped Davis’ knuckles every time he started using heavy vibrato. Davis would carry his clear, signature tone throughout his career. He once remarked on its importance to him saying, “I prefer a round sound with no attitude in it, like a round voice with not too much tremolo and not too much bass. Just right in the middle. If I can’t get that sound I can’t play anything.”

In 1944, the Billy Eckstine band visited East St. Louis. Dizzy Gillespie and Charlie Parker were members of the band and invited Davis to play third trumpet for a couple of weeks with their regular member, trumpeter Buddy Anderson, out with an illness. Even after this experience, once Eckstine’s band left town, Davis’ parents were still encouraging him to continue his formal academic studies.

In the fall of 1944, following graduation from high school, Davis moved to New York to study at the Juilliard School of Music. Upon arriving, he spent most of his first weeks trying to get in contact with Charlie Parker, despite being advised against doing so by several concerned musicians, including saxophonist Coleman Hawkins who believed Parker would not be a positive influence on Davis.

Finally, after locating his idol, Davis became one of a cadre of musicians who held nightly jam sessions at two of Harlem’s nightclubs, Minton’s Playhouse and Monroe’s. The group included future leaders of the bebop revolution: Theodore Fats Navarro, Freddie Webster and J. J. Johnson. Established musicians, including Thelonious Monk and Kenny Clarke, were also regular participants.

Davis dropped out of Juilliard after asking permission from his father. In his autobiography, Davis criticized the Juilliard classes for centering too much on the classical European and “white” repertoire. However, he did acknowledged that in addition to greatly improving his trumpet playing technique, Juilliard helped give him a grounding in music theory that would prove valuable in later years.

Around 1945, Gillespie parted ways with Parker, and Davis was hired as Gillespie’s replacement in his quintet. Davis then finally got the chance to record as a leader in 1946 with an occasional group called the Miles Davis Sextet, plus with vocalists Earl Coleman and Ann Hathaway—one of the rare occasions when Davis, still a member of the Charlie Parker Quintet, can be heard accompanying singers. In these early years, recording sessions where Davis was the leader were the exception, rather than the rule. His next date as a leader would not come until 1947.

During a band stop in Los Angeles, Charlie Parker had a nervous breakdown that landed him in the Camarillo State Mental Hospital for several months. Davis found himself stranded. He roomed and collaborated for some time with bassist Charles Mingus, then got a job on Billy Eckstine’s California tour, eventually bringing him back to New York. In 1948, Parker returned to New York, and Davis rejoined his group.

The relationships within the quintet were growing tense, however. Parker was behaving erratically due to his well-known drug addiction and Davis and Roach caused friction in the group by objecting to having Duke Jordan as a pianist and would have preferred Bud Powell.

By December 1948, Davis’ claims that he was not being paid began to strain the relationship even further. Davis finally left the group following a confrontation with Parker at the Royal Roost.

For Miles, his departure from Parker’s group marked the beginning of a period when he worked mainly as a freelancer and sideman in some of the most important combos on the New York City jazz scene.

In 1948, Davis grew close to the Canadian composer and arranger Gil Evans. The composer’s basement apartment had become the meeting place for several young musicians and other composers, such as Davis, Roach, pianist John Lewis and baritone sax player Gerry Mulligan, who were unhappy with the increasingly virtuoso instrumental techniques that dominated the bebop scene.

Davis wanted to form a jazz group whose objective was to achieve a sound similar to the human voice through carefully arranged compositions, emphasizing a relaxed, melodic approach to the improvisations. He would call this type of this group a “Nonet,” and they debuted in the summer of 1948 with a two-week engagement at the Royal Roost.

The sign announcing the performance gave a surprising prominence to the role of the arrangers: “Miles Davis Nonet. Arrangements by Gil Evans, John Lewis and Gerry Mulligan.” It was so unusual that Davis had to persuade the Roost’s manager, Ralph Watkins, to word the sign this way. He prevailed only with the help of Monte Kay, the club’s artistic director.

The nonet was active until the end of 1949, along the way undergoing several changes in personnel. The presence of white musicians in the group angered some black jazz players, many of whom were unemployed at the time, but Davis rebuffed their criticisms.

Eventually, a contract with Capitol Records was earned and granted the nonet several recording sessions between January 1949 and April 1950. The material recorded was released in 1956 on an album whose title, Birth of the Cool, gave its name to the “cool jazz” movement that developed at the same time and partly shared the musical direction begun by Davis’ group.

Despite its many artistic contributions to jazz, their nonet was not a success, at least not commercially. The liner notes of the first recordings of the Davis Quintet for Columbia Records called it “one of the most spectacular failures of the jazz club scene.” This was bitterly noted by Davis, who claimed the invention of the “cool style” and resented the success that was later enjoyed—in large part because of the media’s attention—to white “cool jazz” musicians (Gerry Mulligan and Dave Brubeck, in particular). This experience also marked the beginning of the lifelong friendship between Davis and Evans, which was an alliance that would bear important results in the years to follow.

The first half of the 1950s for Miles was a period of great personal difficulty. Overseas, Paris and its cultural environment fascinated him, where black jazz musicians and African Americans in general often felt more respected than they did in America. While in Paris, Davis began a short-lived relationship with French actress and singer Juliette Gréco.

Although many of his friends tried to persuade him to stay in France, Davis decided to return to New York. Back in the U.S., he began to feel deeply depressed. He attributed the condition to his separation from Gréco and his feeling of underappreciated by the critics.

Davis blamed these factors for the heroin habit that deeply affected him for the next four years. By 1953, his drug addiction began to impair his playing ability. Heroin had already killed some of his old friends, like fellow trumpeters Theodore “Fats” Navarro and Freddie Webster. Davis was arrested for drug possession while on tour in Los Angeles, and his drug habit became public in a DownBeat magazine interview of Cab Calloway.

Realizing his precarious condition, Davis tried several times to end his drug addiction. He finally succeeded in 1954 after returning to his father’s home in St. Louis for several months and locking himself in a room until he had gone through a painful “cold turkey” withdrawal.

The period of 1950 to 1954 was one of great personal distress, but with musical and professional success for Davis. He would sever his ties to bebop, and the influence of Chicago pianist Ahmad Jamal showed. He later would sign a contract with Bob Weinstock, the owner of Prestige Records. Between 1951 and 1954, Davis released many records on Prestige, with several different combos featuring Sonny Rollins and Art Blakey.

After a widely acclaimed performance at the Newport Jazz Festival in 1955, he signed a long-term contract with Columbia Records and recorded the 1957 album ‘Round About Midnight. It was his first work with saxophonist John Coltrane and bassist Paul Chambers, key members of the sextet he led into the early ‘60s.

During this period, he alternated between orchestral jazz collaborations with arranger Gil Evans, such as the Spanish, music-influenced Sketches of Spain (1960), and band recordings, such as Milestones (1958) and Kind of Blue (1959), which featured harmonies developed by pianist Bill Evans, which was innovative work in the emerging modal jazz style. This particular style uses musical modes rather than chord progressions as a harmonic framework. Blue has become known as one of the most popular jazz albums ever.

Davis made several line up changes while recording Someday My Prince Will Come (1961), and Seven Steps to Heaven (1963), another mainstream success that introduced bassist Ron Carter, pianist Herbie Hancock and drummer Tony Williams.

After adding saxophonist Wayne Shorter to his new quintet in 1964, he led them on a series of more abstract recordings often composed by the band members, helping pioneer the post-bop genre with albums such as E.S.P (1965) and Miles Smiles (1967), before transitioning into his electric period.

During the ‘70s, Davis radically experimented with rock, funk and African rhythms, emerging electronic music technology. He included an ever-changing group of musicians, including keyboardist Joe Zawinul, drummer Al Foster and guitarist John McLaughlin.

This period, beginning with his 1969 studio album In a Silent Way and concluding with the 1975 concert recording Agharta, was the most controversial in Davis’ career, alienating and challenging many in jazz. His platinum-selling 1970 record, Bitches Brew, helped spark a resurgence in the genre’s commercial popularity with jazz-fusion as the decade progressed.

After a five-year retirement due to drug-related health issues, Davis returned to recording new music and performing live in the early 1980s. His return found him employing younger musicians and pop music sounds on albums such as The Man with the Horn (1981) and Tutu (1986). Critics were generally unreceptive, but the decade garnered Davis his highest level of commercial recognition as he performed sold-out concerts worldwide while branching out into visual arts, film and television work.

Miles Davis passed away in 1991, and in 2006 he was inducted into the Rock and Roll Hall of Fame, which recognized him as “one of the key figures in the history of jazz.” Rolling Stone described Davis as “the most revered jazz trumpeter of all time, not to mention one of the most important musicians of the 20th century,” while culture critic Gerald Lyn Early called him “inarguably one of the most influential and innovative musicians of that period.”


Donald Frank “Don” Cheadle Jr. is an actor, writer, producer and director. In 2004, Cheadle earned critical acclaim for his lead role as Rwandan hotel manager Paul Rusesabagina in the film Hotel Rwanda, and was nominated for an Academy Award for Best Actor. In addition, Cheadle won a Golden Globe Award in 2013 for his role in the Showtime comedy House Of Lies. He starred in, directed and co-wrote with Steven Baigelman, Stephen J. Rivele, and Christopher Wilkinson, the film Miles Ahead (2015), based on Miles Davis.

Instead of offering a look at the whole life of Davis, Cheadle concentrates his efforts on incidents in the life of Davis that he feels will both entertain and enlighten. Cheadle took a free-form approach to the film’s narrative. Skipping around in time, it depicts his adventures with a fictional journalist, played by Ewan McGregor—Cheadle felt that the casting of the right causation costar was essential to the film receiving the needed funding to ensure its completion. McGregor’s character wants to profile Davis and his attempts to get his career back on track following a period of drug addiction in the ‘70s. Alone and holed up in his home, Davis is beset by chronic pain from a deteriorating hip. Drugs and pain medications stifle his musical voice, while unsettling ghosts haunt his mind from the past. Davis’ mercurial behavior is fueled by memories of his failed marriage to the talented and beautiful dancer, Frances Taylor (portrayed by actress Emayatzy Corinealdi). During their romance and subsequent marriage, Frances served as Davis’ muse. It was during this period that he released several of his signature recordings, including the groundbreaking Sketches of Spain and Someday My Prince Will Come.

The score for Miles Ahead includes works from Someday My Prince Will Come, as well as—in non-linear fashion—Agharta, Kind Of Blue, Bitches Brew, and We Want Miles among others. Although Don Cheadle’s performance as Miles Davis has been almost universally lauded, which may earn him his second Oscar nomination for best actor, some have criticized Miles Ahead, and Cheadle as director, for not covering events over the entire length and breath of Davis’ storied career. Cheadle was faced with some difficult choices in the planning and execution of the film. If not as all inclusive as some critics may have wanted it to be, Miles Ahead provides an entertaining and provocative portrait of an admittedly small slice of the life of one of our very most important artists. And, if it leaves you and other moviegoers hungry for more, is that such a bad thing?

About Randy Freedman

Chicago freelance writer Randy Freedman is a jazz connoisseur, photographer, food critic, humorist and devoted music fan. He is a regular contributor to Chicago Jazz Magazine.

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