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.

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.

Since then, Cannon has worked with Wynton and Branford Marsalis, Pat Martino, Louis Hayes, The Cannonball Legacy, Ernestine Anderson, Carmen Lundy, Abbey Lincoln, Gary Bartz, Joe Lovano, Monty Alexander, Larry Willis, Eddie Henderson, Steve Turre, Eric Reed, the Dexter Gordon Legacy Ensemble, and many other combinations, as well as with his own quartet.