The Greyboy Allstars debuted in 1993, at the Green Circle Bar, where DJ Greyboy was a DJ. The band's original incarnation included Lenny Kravitz's saxophonist Karl Denson (who also plays flute), guitarist Mike Andrews (Elgin Park), keyboardist Robert Walter, bassist Chris Stillwell, and drummer Zak Najor.
The group came after a successful earlier collaboration of Denson and DJ Greyboy on the Greyboy albums Home Cooking and Freestylin’, featuring Greyboy spinning tracks over the band's instrumentals. Specializing in acid jazz and '60s/'70s soul jazz, Denson has described the Greyboy Allstars as a boogaloo band.
In 1995, the Greyboy Allstars released their first album, West Coast Boogaloo, featuring support from James Brown trombonist and bandleader Fred Wesley, who has also worked with Count Basie and Parliament-Funkadelic, and has arranged for everyone from Ray Charles to Van Morrison.
Two years later, the GBA released their second studio album, A Town Called Earth, in addition to both Robert Walter and Karl Denson issuing solo albums. On both of these solo releases, Walter and Denson were backed by the remaining members of the GBA. Walter's album, titled Spirit of ’70, had additional support from Gary Bartz on alto sax, and Denson's The D Stands for Diesel featured vocalist Andy Bey.
The band released a concert album called Live in 1999. They were dormant for awhile, but began touring again, with most of the original members including DJ Greyboy. Drummer Zak Najor had been replaced by Aaron Redfield (who replaces Eric Kalb).
The band released What Happened to Television? on April 17, 2007, their first album in eight years. Drummer Zak Najor played on the studio recording, but did not go on the subsequent tour. He was replaced by former Deep Banana Blackout drummer Eric Kalb.
Former guitarist Mike Andrews (Elgin Park) helped score the film Donnie Darko, which included he and Gary Jules covering the Tears for Fears song “Mad World.”
On December 30, 2011, 68 year-old trombonist Fred Wesley (Count Basie, Parliament-Funkadelic, Ray Charles, Van Morrison) performed again with the Greyboys, with whom he recorded their debut album West Coast Boogaloo in 1995, at the Belly Up Tavern.
They played the 2012 Hangout Music Fest, held May 18 through 20 in Gulf Shores, Alabama, alongside current-and-former locals Tribal Seeds, Flogging Molly, Switchfoot, and Delta Spirit. Their song “V Neck Sweater,” from their What Happened to Television? full-length, appears on the 2013 SCI Fidelity Records 15th Anniversary Compilation Album..
During the 2020 pandemic, with almost no advance notice, the band dropped their fifth studio album, Como De Allstars, their first studio full-length in seven years. Their lineup at the time included saxophonist Karl Denson, guitarist Elgin Park, drummer Aaron Redfield, bassist Chris Stillwell, and keyboardist Robert Walter.
In summer 2021, the band announced a series of Soul Dream livestream specials featuring four performances (their first of 2021) of material from the soul and jazz ensemble's 30 year career. The series kicked off August 20 with A Town Called Earth, filmed in San Diego and taking its name from the band’s 1997 album, which was be performed in its entirety along with other tracks. The August 27 show, Prestigious, featured songs from artists on New York City’s famed Prestige Records label, including Gene Ammons, Gary Bartz, and Boogaloo Joe Jones. The September 3 edition, Como De Allstars, included a performance of their 2020 album of the same name, along with selections from their 1994 debut record West Coast Boogaloo and Robert Walter’s Spirit of 70. September 10, Get A Job, saw the Allstars playing a mix of covers by Jimi Hendrix, Lonnie Smith, Wynder K. Frog, and more.