Sydney to the Max (TV) Cast
The cast of Sydney to the Max. Updated on August 2, 2025.
34 actors
Ruth Righi
as Sydney Reynolds (63 episodes)

Ruth Righi plays Sydney Reynolds, a 12-year-old girl living in Portland, Oregon, dealing with the challenges of middle school alongside her best friend Olive.

Ava Kolker
as Olive (63 episodes)

Ava Kolker portrays Olive, Sydney's best friend, who accompanies her through the ups and downs of middle school life.

Ian Reed Kesler
as Max Reynolds (63 episodes)

Ian Reed Kesler plays Max Reynolds, Sydney's father, who supports her while also reflecting on his own youth.

Caroline Rhea
as Judy (63 episodes)

Caroline Rhea stars as Judy, Sydney's paternal grandmother, who lives with the family and provides guidance to both Sydney and Max.

Jackson Dollinger
as Young Max (63 episodes)

Jackson Dollinger plays Young Max, offering a glimpse into the past of Sydney's father during his own childhood in flashback scenes.

Christian J. Simon
as Leo (63 episodes)

Christian J. Simon portrays Leo, who is a close friend of Young Max in the flashbacks, adding to the nostalgic moments of the show.

Lumi Pollack
as Jorden (63 episodes)
Nicolas Cantu
as Dominic (1 episode)
Reid Shapiro
as Iggy (3 episodes)
Buddy Handleson
as Gerald (1 episode)
Jeffrey Cade Ross Brown
as Kyle (1 episode)
Winston A. Marshall
as Grown Up Leo (1 episode)

Winston A. Marshall plays Grown Up Leo, showing what the character has become in the present day.

Judith Moreland
as Ms. Watkins (1 episode)
Joachim Powell
as LJ (1 episode)
Wyatt Walter
as Riccoli (2 episodes)
Melissa Peterman
as Mrs. Harris (2 episodes)
Krystal Joy Brown
as Dr. Alicia Reynolds (1 episode)
Eric Allan Kramer
as Coach Carlock (1 episode)
Griffin Kunitz
as Adam (1 episode)
Arjun Sriram
as Pete (1 episode)
Max Torina
as Luke (1 episode)
Thalia Tran
as Suzie Harrison (1 episode)
Merrick Hanna
as Joe (1 episode)
Connor Falk
as Harry (4 episodes)
Aniya Simone
as Lexi (3 episodes)
Carlease Burke
as Mya (1 episode)
Kale Culley
as Ryan (1 episode)
Brandon Rossel
as Jake (1 episode)
Izzy Lieberman
as Bryce (1 episode)
Lauren Price
as Student (1 episode)
Jaxon Goldenberg
as Matt (1 episode)
Jolie Jenkins
as Gemma (1 episode)
Luca Alexander
as Zach (2 episodes)
Mason Blomberg
as Young Harry (1 episode)
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