[12] R&B-influenced Willis Gator Jackson was easiest to grasp at first, but soon he identified the sounds of Sonny Rollins,[13] John Coltrane, and Miles Davis as his principal influences.

[14] After high school graduation, Holloway practiced 8–12 hours a day and sat in with bands of kinds in jam sessions, which increased his versatility.

[15][16] As the Washington D.C. music scene continued to thrive in the 1970s, Holloway joined popular R&B groups the Sounds of Shea and Mad Dog and the Lowlifers.

[24] In 1979 Root Boy, Holloway and the rest of the Sex Change Band participated in a film entitled Mr. Mike's Mondo Video which was written by Michael O'Donoghue of Saturday Night Live.

Holloway recorded four albums with Root Boy and at least three 45's: "Too Much Jawbone" with "Xmas at K-Mart" on the flip side, "The Meltdown" backed with "Graveyard of Losers" and "Dare to Be Fat" on I.R.S.

Holloway first met Osiris Marsh in 1979 and found their influences included bands with eclectic tastes ranging from Parliament-Funkadelic, Earth, Wind, and Fire, and Sly and the Family Stone.

Another album, O-Zone on Marlin Records, met with similar reviews and faced the same overall inability to overcome the dance floor fever that enticed many funk and soul listeners towards disco as the 1970s came to an end.

[28] In November 1981 Holloway visited a landmark D.C. club; Blues Alley, where he had been told jazz drummer Norman Connors would be performing.

Afterward, Holloway was approached by singer and spoken word artist, Gil Scott-Heron, who complimented him and extended an offer to join his group, the "Amnesia Express".

[29] In February 1982 Holloway played his first concert with Scott-Heron at The Bottom Line in New York City with fellow saxophonist and Amnesia Express co-founder Carl Cornwell.

[31][32] It happened that, early in 1982, Holloway was on board when filmmaker Robert Mugge documented Scott-Heron's concert at the Wax Museum nightclub in Washington, D.C.

[29] Though he was a member of Scott-Heron's group during this period, Holloway continued to appear with Gillespie whenever he would perform in D.C.[34] In June 1989 he was sitting in with Dizzy at Blues Alley.

The next year, in the summer of 2005, guitarist Jack Pearson and Holloway toured with The Allman Brothers Band, filling in for an ailing Warren Haynes.

[57][58] It was the beginning of many performances where Holloway appeared with The Allman Brothers Band and Gov't Mule, playing the Beacon Theatre in New York City, Nissan Pavilion in Bristow, Virginia, the Wanee Festival in Live Oak, Florida,[59] Merriweather Post Pavilion in Columbia, Maryland,[60] Warner Theatre (Washington, D.C.)[61] and The Warren Haynes Christmas Jam,[62][63][64] which Haynes hosts annually, in Asheville, North Carolina.

[65] In October 2005 Holloway finally heard blues and soul singer, Susan Tedeschi perform with her own group at Rams Head Live!

Tedeschi and Holloway met previously a couple of years before while guesting with her husband, Derek Trucks, at the Wanee Festival and a show at The Birchmere, (in suburban Virginia, just outside Washington, D.C.).

For the next few years, the band toured across Europe[66][67] and extensively throughout the United States, playing major festivals,[68] concert halls,[69] theaters[70] and clubs.

Tedeschi, along with her band have also appeared on Late Night with Conan O'Brien[71] and have been seen on countless local news spots as they toured across the United States.

[73] In February 2009, Warren Haynes began work on a solo project at Pedernales Studio, in Austin, Texas, with Gordie Johnson as co-producer and engineer.

[77][78] The group line-up was; Warren Haynes (lead vocals/guitar), Ivan Neville (keys/vocals), Ron Johnson (electric bass), Terence Higgins (drums), Ruthie Foster (vocals) and Holloway (tenor saxophone).

Holloway traveled to Memphis, Tennessee, and spent two days recording with the band at Ardent Studios[80] for Honeytribe's sophomore release; Space Age Blues.