The characters of Sydney to the Max.
Main characters
Sydney Wallace Reynolds
The central main character; a Biracial pre-teen who navigates the ups and downs of her life.
- Affectionate Nickname: Max, Olive, and Judy call her Syd while Judy often calls her Noodle.
- Expository Hairstyle Change: Starting from "The Hair Switch Project", she now wears her hair naturally and has it consistently in an African ponytail with a double parting and braids.
- Missing Mom: Her mom passed away five years ago.
Maxwell Keith "Max" Reynolds
Sydney's widowed father. He is shown to experience similar problems as her in his youth.
- Attention Deficit... Ooh, Shiny!: Max is bothered when he is nominated for the 7th grade “space cadet” award due his tendency to space out. Judy helps Max realize that his wandering mind can be an asset.
- Deadpan Snarker: He has his moments.
- Cannot Spit It Out: As shown in Season 3, he cannot bring himself to confess his feelings to Alisha.
- Catchphrase: Max often says, "Gah!" when something goes wrong for him.
Olive Anne Rozalski
Sydney's best friend.
- Drop-In Character: She spends most of her time with Sydney because of the madness at her house.
- Informed Judaism: Mentions celebrating Hanukkah in "How the Syd Stole Christmas".
- Invisible Parents: Her parents have yet to appear on the show outside of mentions. Her mom finally appears in "Rock the Float!".
- Shipper on Deck: In "When Harry Met Sydney", she thinks Sydney and her childhood best friend Harry are the perfect match for each other.
Leonard Lawrence "Leo" Webb
Max's best friend from his youth. In the present, he currently resides in San Francisco.
- Anime Hair: Has a rather unique-looking hairstyle when older.
- Black and Nerdy: In the past, Leo is the more studious and cautious of the pair. In the present, he runs a tech company in San Francisco.
Judy Reynolds
Sydney's grandmother and Max's mother.
- Cool Old Lady: She's shown to be hip and progressive.
Supporting Characters
Sydney's African American mother; she died five years before the series.
- Ascended Extra: In Season 3 because of the overarching Myth Arc focusing on Max forming a crush on her and slowly gaining the confidence to confess his feelings.
A pizza delivery boy who is close with Sydney and Olive.
- Hidden Depths: He got a perfect score on his SAT.
The coolest kid in school. Sydney and Olive crush on him.
- Chuck Cunningham Syndrome: Hasn't been seen since Season 1.
One of Sydney and Olive's friends. She's the tomboyish of the group.
Another friend of Sydney and Olive, she's the naïve and ditzy member.
Sydney and Olive's history teacher.
The poetry teacher at Clara Barton Middle School. Sydney and Olive have a strong bond with her.
Sophia's always controlling mother.
- Sitcom Arch-Nemesis: To Sydney, due to her controlling attitude.
Sydney's childhood friend who moved away in second grade. He moves back to Portland in Season 3.
- Limited Social Circle: Harry and Sydney agree to take a break from hanging out when Sydney realizes that spending so much time with Harry has limited his ability to make new friends.
