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 , Ian Reed Kesler as Max , Christian J. Simon as Leo , Ava Kolker as Olive , Caroline Rhea as Judy , and newcomer Jackson Dollinger as Young Max .