Sydney to the Max features Sydney Reynolds ( School of Rock ) , Ian Reed Kesler , ( Suits , Kickin ' It ) , Christian J. Simon ( The Amazing World of Gumball ) , Ava Kolker ( Girl Meets World ) , Caroline Rhea ( Sabrina the Teenage Witch , Phineas and Ferb ) , and Jackson Dollinger ( Puppy Dog Pals ) .
Starring in the series are Ruth Righi as Sydney Reynolds ( School of Rock ) , Ian Reed Kesler as Max ( Suits , Kickin ' It ) , Christian J. Simon as Leo ( The Amazing World of Gumball ) , Ava Kolker as Olive ( Girl Meets World ) , Caroline Rhea as Judy ( Sabrina the Teenage Witch , Phineas and Ferb ) , and newcomer Jackson Dollinger as Young Max ( Puppy Dog Pals ) .