He was a sideman in Art Blakey's Jazz Messengers for two periods (July 1958 to September 1959; February 1960 to June 1961), between which he was part of Cannonball Adderley's band.

Several of Timmons' compositions written when part of these bands – including "Moanin'", "Dat Dere", and "This Here" – enjoyed commercial success and brought him more attention.

He went on to play and record with Chet Baker in 1956–57 (bassist Scott LaFaro was part of this band for a time[7]), Sonny Stitt in 1957, and Maynard Ferguson in 1957–58.

Timmons became best known as a member of Art Blakey's band the Jazz Messengers, which he was first part of from July 1958 to September 1959, including for a tour of Europe.

[13] Timmons was reported to be dissatisfied with the money he had received from "This Here", and was enticed in February 1960 into leaving Adderley and returning to Blakey's band by the offer of more pay.

[14] In the same year, he played on recordings led by Nat Adderley,[15]: 13  Arnett Cobb,[15]: 307  and Johnny Griffin,[15]: 670  among others; on the first of these, Work Song, Timmons did not appear on all of the tracks, because he had been drinking heavily.

[16] Timmons left Blakey for the second time in June 1961,[1] encouraged by the success of his compositions, including jukebox plays of "Dat Dere", which Oscar Brown had recorded after adding lyrics.

[18] According to Tootie Heath, Timmons was at the peak of his fame at that point, but was addicted to heroin, and used a lot of the money that the band was paid maintaining his habit.

[19] In 1963, Timmons' playing, with Lewis Powers on bass and Roy McCurdy on drums, was described by a Washington Post reviewer as "flexible and adventuresome [...] Glossing over everything is an undeniable sheen of church music and spirituals.

[12] In the following year, he played in a quartet led by Sonny Red,[25] with Dexter Gordon on one of the saxophonist's temporary returns to the US from Europe,[26][27] and in a trio backing vocalist Etta Jones.

[36] The Penguin Guide to Jazz suggested that "Timmons' characteristic style was a rolling, gospelly funk, perhaps longer on sheer energy than on harmonic sophistication.

"[37] Gary Giddins, however, highlighted other facets of Timmons' playing: the "lush [Bud] Powell-inspired ballads, his clear, sharp, unsentimental long lines.

"[24]: 50  Carter also identified Powell as a primary influence on Timmons, and commented that his partner in the trio "was very giving, very loyal, played every night like it was his last chance to get it right.

"[18] The funky aspects of Timmons' playing influenced fellow pianists, including Les McCann, Ramsey Lewis, and Benny Green.