Born in Racine, Wisconsin, he attended The University of Wisconsin at La Crosse where he met jazz player Milt Hinton. Cannon also studied at the Wisconsin Conservatory of Music in Milwaukee.
Cannon moved to New York City at age 28, and he started to play at the Blue Note Jazz Club with musicians Winard and Philip Harper and Justin Robinson. From there, he moved to gigs with Art Blakey's Jazz Messengers, Dexter Gordon, Cedar Walton Trio with Billy Higgins, Jimmy Smith, Jimmy Scott, James Williams, Hamiett Bluiett, Ed Thigpen, Frank Foster, John Bunch, Eddie Harris, Stanley Turrentine and Bunky Green. When trumpeter Roy Hargrove came to a club where Cannon was working, they met. For the next seven years, Cannon performed as a member of Hargrove's band at major jazz festivals all over the world, including the North Sea Jazz Festival, Cape Town Jazz Festival, Montreux Jazz Festival, Umbria Jazz Festival in Perugia, and the Montreal Jazz Festival. He also was a part of the award-winning Crisol tour where Cannon played with Cuban musicians like percussionist Jose Luis "Chanquito" Quintana, Miguel "Anga" Diaz, Horacio "El Negro" Hernandez, and Chucho Valdes and studied with bassist Orlando "Cachahito" Lopez and pianist Ruben Gonzalez.
Cannon carries the knowledge passed on to him by bassists Ray Brown, Sam Jones, Ron Carter, and Buster Williams and continues the legacy by conducting master classes throughout the U.S. and Europe. He taught at the Oberlin Conservatory in 2014, the Wisconsin Conservatory of Music in Milwaukee, and the New School in New York and at Long Island University. He also gave a number of master classes at the University of Wisconsin in Whitewater and Eau Claire, at Emory University in Atlanta, Georgia and at the Conservatory of Amsterdam. Cannon was also a faculty member of the Conservatory of Maastricht, Holland. Cannon is currently Jazz Bass Instructor at JUILLIARD School (New York), Associate Professor of Jazz Bass at OBERLIN College & Conservatory (Ohio),and on the Board of the Directors at the Wisconsin Conservatory of Music.
2020: Shuffle and DealEddie Henderson, Donald Harrison, Kenny Barron, Gerald Cannon, Mike Clark (SMOKE SESSIONS Records)
2021: Fallen HeroesWillie Jones III,Willie Jones, Jeremy Pelt, Sherman Irby, George Cables, Gerald Cannon, Steve Davis, Justin Robinson, Isaiah Thompson, Renee Neufville, WJ3 Records
2022: The Ways in James Zollar JZAZ Records
2022: New Beginnings Jason Marshall Cellar Music Group Records