Jimmy Chance (Lucas Neff)
A dense but goodhearted guy, Jimmy starts off the series with an identity crisis when he realizes how monotonous his life is. He starts searching for his place in the world, never expecting the path his life would take after meeting Lucy. Although previously a slacker and didn't amount to much, he tries really hard to raise Hope right and that honesty and determination has a ripple effect among those around him.
Virginia Chance (née Thompson) (Martha Plimpton)
Jimmy's mother, she has worked as a maid for years and is always cleaning houses of people far wealthier than her family. As a result she has a bit of a complex about how others see them, while leading to its own zany adventures it also keeps her away from more inappropriate behavior. She is protective of her family but also very loving.
Jimmy's father, they both work in Burt's lawn care and pool cleaning business. He is very friendly and outgoing, always concerned with the well-being of his friends and family. He greatly enjoys the time he spends with his son and tends to find humor and enjoyment in the little things of life.
Sabrina Collins (Shannon Woodward)
A girl Jimmy met shortly after he took custody of Hope, her sarcastic but friendly demeanor meshes well with Jimmy's raw honesty. Despite his crush her long time boyfriend prevents anything beyond some mild flirting. When that ran its course she and Jimmy got together and eventually marry, with her adopting Hope.
- A-Cup Angst: A minor insecurity and brought up a few times.
- Character Development: From a critical Deadpan Snarker, almost Satellite Love Interest, to a deep, open-minded, loving, and slightly Cloudcuckoolander character, with all this development's base being here almost since the beginning.
- Deadpan Snarker
- Four-Temperament Ensemble: Melancholic
- Fun Size: She is really short, Burt and Virginia mention it is their go-to joke about her.
- Happily Married: To Jimmy.
- Hidden Heart of Gold
- Inferiority Superiority Complex: With rich people who succeeded better in their career.
- Mama Bear: To Hope.
- Milholland Relationship Moment: Has one of these with Jimmy, reciprocally, as both accept each other's bad points.
- Oblivious to Love: To Jimmy until about midway through season two.
- Parental Neglect: The flashback in "Arbor Daze" reveals her parents barely paid any attention to her, treating her more as a nuisance (father) and a bartender (mother) who barely tolerated her. She makes a promise to her doll that she wouldn't do that with her child.
- Parents as People
- Parental Substitute: To Hope.
- Secretly Wealthy: Her parents are very rich, but she has relied on her own work to get by as a form of protest.
- The Snark Knight
- Sugar and Ice Personality
The show namesake, she grows up over the course of the series. Generally cheerful as most babies are, she is exceptionally smart but some of the family is concerned about her parentage and what that means for when she gets older.
Barbara-June "Maw Maw" Thompson (Cloris Leachman)
Virginia's grandmother and the one who raised her (also being Jimmy's great grandmother and Hope's great-great grandmother), the house is actually in her name. She suffers from a combination of memory loss and dementia, which the rest have to deal with on a regular basis. Sometimes a real chore to deal with, but at other times someone who really livens up the room.
Barney Hughes (Gregg Binkley)
Store manager for Howdy's, he is Sabrina and Jimmy's boss. Easily excitable, he is often the butt of some prank Sabrina pulls out of boredom.
- Ascended Extra: After joining the main cast.
- Camp Straight: Very finicky and loves collecting dolls, Sabrina notes with amusement that he isn't gay.
- Formerly Fat: Use to be 100 pounds heavier.
- Has Two Mommies: Often talks about his moms.
- Promotion to Opening Titles: Shows up a few times in the first season and got his own title card in the opening sequence for the second season. While he still doesn't show up in every episode, he is in most of them.
- Sixth Ranger: Often joins the chances on their escapades.
Shelly (Kate Micucci)
Sabrina's cousin, she runs a multi-purpose daycare (children, the elderly and pets) and babysits Hope. Talented with the ukelele
, she is always ready with a little jingle.
- Cloud Cuckoolander: Not as badly as Frank, but it does crop up ocasionally.
- Cute Bruiser: She takes Krav Maga with Burt, once managing to pull him into submission.
- In Vino Veritas: She gets really frisky when she drinks.
- Official Couple: With Frank.
- Out of Focus: In Season's 1 and 2 she's a fairly major recurring character and her daycare is a frequent spot for Maw Maw and Hope. In Season's 3 and 4 she appears in about 8 episodes between both seasons and her daycare mysteriously disappears.
- Ship Tease: She and Jimmy made out at a party several years prior and while she seemed interested in starting something, Jimmy didn't return the feelings (due to being hung up on Sabrina).
Frank (Todd Giebenhain)
A co-worker of Sabrina and Jimmy, Frank is exceptionally odd and creepy, but he is otherwise a decent guy who befriends Jimmy.
- Cloud Cuckoolander:An intresting variant. Instead of being cute and whimsical, he tends to stop conversations dead in their place.
- Heterosexual Life-Partners: With Jimmy, although he is much more devoted to Jimmy than the other way around. It is notable that they became good friends because they can hang out at work, as Javier and Marcus stopped hanging with Jimmy because of his obligations with Hope.
- Hidden Depths: He built a miniature scale model of Natesville in his house. While that alone is still creepy, Jimmy can't help but be impressed with the creativity and detail involved.
- Official Couple: With Shelly.
- Odd Friendship: With Maw Maw.
- Perpetual Frowner
- Jerk with a Heart of Gold: He's fairly blunt and creepy most of the time, but he genuinley cares about Jimmy.
- This is shown in spades when he finds out Shelly was the girl he had been video chatting while wearing a baby head mask. He's genuinley distraught when a russian grocery clerk steals her away and gives her a rather sweet heartfelt confession later.
- Parental Abandonment: His parents apparently left him when he was 17 and he lives alone.
- Wacky Guy: Albeit a low key, disturbing example.
Javier and Marcus (Ray Santiago and Jermaine Williams)
Jimmy's longtime friends, they are never seen apart from each other
. Still friendly with Jimmy, they aren't seen very often because Hope restricted a lot of what Jimmy was willing to do.
Lucy Carlyle (Bijou Phillips)
Hope's mother after a one night stand with Jimmy. She is actually quite intelligent, but a pushover who eventually snapped when she had enough.
- Big Bad: The closest thing the show has to one.
- Bigger Bad: The family frequently worries Hope will turn out like her.
- Cute and Psycho
- Even Evil Has Loved Ones: She actually loves her daughter immensely and would never harm her.
- Not Quite Dead: Turns out to have surivied her execution. She ends up getting hit by a bus... and survives again.
- Posthumous Character: She shows up in flashback at random times, notable especially in the first season finale when it shows her Start of Darkness. At least it is this trope until it's revealed she was alive after her apparent execution.