The period from the mid 1950's until the mid 1960's represents the heyday of mainstream modern jazz. Many of those now considered among the greatest of all time achieved their fame in this era.

Miles Davis had four important groups during this time. The first featured John Coltrane ("Trane") on tenor saxophone, Red Garland on piano, Paul Chambers on bass, and "Philly" Joe Jones on drums. This group is sometimes considered the single greatest jazz group ever. Most of their albums are available today, including the series of Workin' ..., Steamin' ..., Relaxin' ..., and Cookin' with the Miles Davis Quintet. Miles perfected his muted ballad playing with this group, and the rhythm section was considered by many to be the hardest swinging in the business. The second important Davis group came with the addition of alto saxophonist Julian "Cannonball" Adderly and the replacement of Garland with Bill Evans or Wynton Kelly and the replacement of Jones with Jimmy Cobb. The album Kind Of Blue from this group is high on most lists of favorite jazz albums. The primary style of this group is called modal, as it relies on songs written around simple scales or modes that often last for many measures each, as opposed to the quickly changing complex harmonies of bebop derived styles. The third Davis group of the era was actually the Gil Evans orchestra. Miles recorded several classic albums with Gil, including Sketches Of Spain. The fourth important Miles group of this period included Wayne Shorter on saxophone, Herbie Hancock on piano, Ron Carter on bass, and Tony Williams on drums. The early recordings of this group, including Live At The Plugged Nickel, as well as the earlier My Funny Valentine, with George Coleman on saxophone instead of Wayne Shorter, mainly feature innovative versions of standards. Later recordings such as Miles Smiles and Nefertiti consist of originals, including many by Wayne Shorter, that largely transcend traditional harmonies. Herbie Hancock developeda new approach to harmonization that was based as much on sounds as on any conventional theoretical underpinning. John Coltrane is another giant of this period. In addition to his playing with Miles, he recorded the album Giant Steps under his own name, which showed him to be one of the most technically gifted and harmonically advanced players around. After leaving Miles, he formed a quartet with pianist McCoy Tyner, drummer Elvin Jones, and a variety of bass players, finally settling on Jimmy Garrison. Coltrane's playing with this group showed him to be one of the most intensely emotional players around. Tyner is also a major voice on his instrument, featuring a very percussive attack. Elvin Jones is a master of rhythmic intensity. This group evolved constantly, from the relatively traditional post bop of My Favorite Things to the high energy modal of A Love Supreme to the wailing avant garde of Meditations and Ascension.

Charles Mingus was another influential leader during this period. His small groups tended to be less structured than others, giving more freedom to the individual players, although Mingus also directed larger ensembles in which most of the parts were written out. Mingus' compositions for smaller groups were often only rough sketches, and performances were sometimes literally composed or arranged on the bandstand, with Mingus calling out directions to the musicians. Alto saxophonist, bass clarinetist, and flautist Eric Dolphy was a mainstay of Mingus' groups. His playing was often described angular, meaning that the interval in his lines were often large leaps, as opposed to scalar lines, consist mostly of steps. The album Charles Mingus Presents Charles Mingus featuring Dolphy is a classic.

Thelonious Monk is widely regarded as one of the most important composers in jazz, as well as being a highly original pianist. His playing is more sparse than most of his contemporaries. Some of his albums include Brilliant Corners and Thelonious Monk With John Coltrane. Pianist Bill Evans was known as one of the most sensitive ballad players, and his trio albums, particularly Waltz For Debby, with Scott LaFaro on bass and Paul Motian on drums, are models of trio interplay. Wes Montgomery was one of the most influential of jazz guitarists. He often played in groups with an organist, and had a particularly soulful sound. He also popularized the technique of playing solos in octaves. His early albums include Full House. Later albums were more commercial and less well regarded. Tenor saxophonist Sonny Rollins rivaled Coltrane in popularity and recorded many albums under his own name, including Saxophone Colossus and The Bridge, which also featured Jim Hall on guitar. Sonny also recorded with Clifford Brown, Miles Davis, Bud Powell, Thelonious Monk, and other giants.

Other noteworthy musicians of the era include saxophonists Jackie McLean, Dexter Gordon, Joe Henderson, and Charlie Rouse; trumpet players Freddie Hubbard, Lee Morgan, Woody Shaw, and Booker Little; trombonists J. J. Johnson and Curtis Fuller; clarinetist Jimmy Guiffre, pianists Tommy Flanagan, Hank Jones, Bobby Timmons, Mal Waldron, Andrew Hill, Cedar Walton, Chick Corea, and Ahmad Jamal; organist Larry Young, guitarists Kenny Burrell and Joe Pass; guitarist and harmonica player Toots Thielemans; vibraphonist Bobby Hutcherson; bassists Ray Brown, Percy Heath, Sam Jones, Buster Williams, Reggie Workman, Doug Watkins, and Red Mitchell; drummers Billy Higgins and Ben Riley; and vocalists Jon Hendricks, Eddie Jefferson, Sarah Vaughan, Betty Carter, Carmen McRae, Abbey Lincoln, and Shirley Horn. Big bands such as those of Woody Herman and Stan Kenton also thrived.