[citation needed] At 19, he started to play with local bands and, months later, worked for the first time with such musicians as Dizzy Gillespie and Max Roach.

[8] Roach introduced Mobley to the New York jazz scene in 1951, and over the next two years the latter began composing and recording tunes of his own.

[2] When Charlie Parker heard Mobley's playing, he advised the young musician to take more influence from blues music.

He and Blakey took part in one of the earliest hard bop sessions, alongside pianist Horace Silver, bassist Doug Watkins and trumpeter Kenny Dorham.

Mobley recorded steadily during the second half of the 1950s for Blue Note records, a series of albums which featured him with Lee Morgan, Donald Byrd, Art Farmer, Kenny Dorham, Jackie McLean, Pepper Adams, Milt Jackson, Sonny Clark, Bobby Timmons, Herbie Hancock, Wynton Kelly, Paul Chambers, and Philly Joe Jones, among others.

In a 2020 review of Soul Station, The Recording Academy's Grammy Awards website called the album Mobley's "most rewarding listen despite not breaking the mold.

"[14] The Guardian gave Mobley's four "classic" albums (Peckin’ Time, Soul Station, Roll Call and Workout) five stars noting that "[f]or once, the word 'classic' is justified."

[15] During this period of his career, he performed with bop and hard bop musicians including Grant Green, Freddie Hubbard, Sonny Clark, Wynton Kelly and Philly Joe Jones, and formed a particularly productive partnership with trumpeter Lee Morgan, having appeared on each other's albums and Johnny Griffin's A Blowin' Session.

Both featured a rhythm section of Wynton Kelly, Paul Chambers, and Philly Joe Jones, all of whom were in Davis's bands during the late 1950s.

[9] Alfred Lion, co-producer of the label, would frequently direct the band's tempo or critique studio takes until he was pleased with them.

[2][20] According to Samuel Chell, No Room for Squares was "the first session on which [Mobley] would begin to sacrifice lyric inspiration and subtlety of phrasing to a harder sound and stiffer rhythmic approach.

"[18] In 1964, while serving a prison sentence for narcotics possession, Mobley wrote songs that were later recorded for the album A Slice of the Top.

[21] One of Mobley's final albums, titled Breakthrough!, was recorded in 1972 with baritone saxophonist Charles Davis, pianist Cedar Walton, bassist Sam Jones, and drummer Billy Higgins.

[25] He worked two engagements at the Angry Squire in New York City – November 22 and 23, 1985, and January 11, 1986 – in a quartet with Duke Jordan and guest singer Lodi Carr, a few months before his death.

[30] The Spectator lamented that "an unfortunate side effect of 20th century Modernism is that [listenability] doesn't put you in the history books," referencing Mobley's style and the lack of attention paid to his work, as compared to John Coltrane and Sonny Rollins.

According to fellow saxophonist Gary Bartz, the fact his compositions were not organized with one publishing company made profiting from them difficult.