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The Sapersteins
Jean-Ralphio Saperstein
Jean-Ralphio Saperstein
"I made my money the old-fashioned way. ♪ I got run over by a Lexus ♪"
Played By: Ben Schwartz
"I heard 'sack of flour' and 'high school'. Are you ding-dongs making fake drugs for sophomores? Because if true, this guy wants in!"
Tom's partner-in-crime who is somehow even more obnoxious and slimier than Tom is. He's hilarious just from his hairstyle to his eccentric personality. Outright hated by Ron and Donna.
- Abhorrent Admirer: Towards Leslie, though in the most benign and Played for Laughs fashion possible, and he's generally pretty respectful about it.
- Ambiguously Bi: Or, in his words, "I guess you could say I'm ♫open-minded as helllll!♫" In this example, he was propositioning the pregnant Ann ("the more the merrier!"); when her husband Chris objected, Jean-Ralphio told him that he could come, too.
- Breakout Character: A fan favorite from his debut, which led to him making several more appearances as well as the introduction of his sister and father.
- Casanova Wannabe: Even more so than Tom. He frequently makes passes at the other female characters with no success.
- Conspicuous Consumption: In his own words, the only thing better than having money is making sure people know you have it.
- Everyone Has Standards: He's the first person to admit how horrible Mona-Lisa is. And he's her brother.
- Faking the Dead: At some point in the future, he fakes his death and plans to use the insurance payout to open a casino in Tajikistan.
- The Friend Nobody Likes: Nobody but Tom likes him, and even Tom starts to get annoyed with him later on.
- Graceful Loser: Whenever he loses a job or gets rejected in an interview, Jean-Ralphio simply acknowledges that it's the right decision.Employer: (after Jean-Ralphio's been employed for about thirty seconds) You're fired!
Jean-Ralphio: Makes sense. So I just go out the same way I came in? - Idle Rich: Though he does try to get a job, he's not good at it. He's okay with it though.
- Incoming Ham: Someone making an indirect comment about him without using his name directly will inevitably summon Jean-Ralphio.
- Jerk with a Heart of Gold: He's definitely a slimeball, very self-centered, and incredibly obnoxious, but he's not really a bad guy. He actually does care about Tom and admits his own shortcomings freely. He's just very spoiled, very overconfident, and comes on way too strong.
- Large Ham: Constantly loud, if not outright yelling (or singing). When directly asked why he acts that way, he says "PIIIILLLLS BABY!"
- Replacement Flat Character: He embodies all of the negative traits Tom had before he got character development.
- Spoiled Brat: He has no work ethic whatsoever (though he doesn't always sit around doing nothing) and asks for money from his father (who he calls "Daddy") all the time. Which he gets.
- Toxic Friend Influence: To call him a bad influence on Tom would be an understatement.
- Upper-Class Twit: He's the son of a rich doctor and is as dense as a black hole.
- Verbal Tic: Will occasionally rand-om-ly sing woorrrrds in his sen-ten-ceeees!
- He's also weirdly incapable of making rhyming couplets, wherein he'll hit the intended rhyme, but ruin it by adding another word after it.
- With Friends Like These...: Generally sees Tom as little more than an extra source of cash, though he does genuinely seem to like him.
Mona Lisa Saperstein
Mona Lisa Saperstein
"MONEY PLEEAAAAAASE!!"
Played By: Jenny Slate
"I totally hear you, but I also don't like what you're saying. So if you say "no", I will start a fire in the bathroom."
Jean-Ralphio's "twin sister from the same mister" who he describes as (singing) "the worst person in the wooooorld" and also a "total klepto, nympho, and pyro". Tom hires her at his clothing rental business and ends up starting a relationship with her after attempting to discipline her results in a sexual encounter.
- Ax-Crazy: Frequently breaks things and sets fires when she doesn't get her way, picks fights with people and is an all-around unstable person.
- Brutal Honesty: She has absolutely no filter and will openly comment on people's appearances without any provocation. In one instance, she insulted a small child and told him that a jacket he wanted to rent was ugly.
- Card-Carrying Jerkass: She gleefully admits to being a terrible person.
- Character Catchphrase: "Moneeeeey, pleeeeeaase!" She usually says this to her father (who immediately hands her wads of cash when she does), but has been shown to do it to others.
- Cute and Psycho: She's cute, but along with being intolerable, she's a complete psychopath.
- Daddy's Girl: Like her brother, she blatantly lies to their father's face and whines to get money at the drop of a hat.
- Distaff Counterpart: Is essentially a female Jean-Ralphio, except somehow even more obnoxious and eccentric.
- Extreme Omnisexual: She is perfectly open to having a foursome with Tom, Craig (a total stranger), and her own brother. In another instance, she offers to have a three-way with Tom and Ann; when Ann turns her down, Mona Lisa turns to another random woman (who she has never met) and offers her a place in the threesome instead. The one exception to this is Garry (unsurprisingly), whom she gives a "hard pass" to.
- Freudian Excuse: A comic version. It's implied that she became so spoiled because her father constantly indulges her every whim and hands her money whenever she demands it (largely because that's easier than dealing with her tantrums).
- The Friend Nobody Likes: Tom dates her. Jean-Ralphio is her brother. Both of them admit that Mona Lisa is a horrible person.
- Hated by All: While Jean-Ralphio is at least liked by Tom, everyone hates Mona Lisa, including her brother, her father, and her boyfriend.
- Idle Rich: Gets her money from her father, and just fools around all day. For a time she was employed by Tom, but she was awful at it.
- Insult Backfire: Any attempt to call her out on her horrific behavior or tell her that she's impossibly spoiled and childish results in her agreeing with the statement. She knows she's greedy, manipulative, and selfish, and doesn't particularly care.
- Jerkass: She is, in fact, the wooooooooooorst.
- Jewish American Princess: She is very spoiled and Ambiguously Jewish, although she is not the least bit sexually repressed.
- Kissing Cousins: She French-kissed her cousin once... and may still be in love with him. Tom is understandably disgusted.
- Never My Fault: To quote her directly, "I have done nothing wrong, ever, in my life."
- Psychopathic Womanchild: Whereas Jean-Ralphio is a slimeball but otherwise harmless, Mona Lisa is a few paintings short of a Louvre. Case in point, the way she childishly asks for money while smashing up Ben's office is a hilarious and terrifying thing to watch.
- Pyromaniac: She loves to set fire to things—usually because she's either bored or demanding concessions from people.
- Really Gets Around: She'll agree to anything with anyone. Except Jerry.
- Selective Obliviousness: Mona-Lisa only "listens" to other people when they're telling her what she wants to hear (and even then she's barely paying attention). She once told Tom that she needed to leave work early to see a Pitbull concert; when he told her no, she outright stated "I don't like what you're saying" and threatened to start a fire in the bathroom if she didn't get her way.
- Shared Family Quirks: She has the same ten-den-cyyyy to breeeak into sooooooong as her bro-therrrrrr!
- The Sociopath: Played for Laughs. She has absolutely no sense of morality (she once told Tom she was pregnant and sent him into a panic because she thought it was funny) and possesses zero regard for property: she sets fire to her father's car because he's taking too long in a meeting with Ben, then goes into the office where said meeting is being held, demands money from Ben, and, when she doesn't get it, starts destroying furniture. The only thing that matters to her is her own enjoyment; other people, things, and emotions mean nothing.
- Spoiled Brat: Even more so than her brother.
- Tantrum Throwing: When she doesn't get her way, she immediately breaks into incredibly destructive fits and starts breaking anything she can get her hands on.
- Tranquil Fury: A large part of the humor of her massive, property-destroying tantrums is how calm she is during them. She remains gentle and even pleasant as she starts trashing Ben's office, happily describing what she's going to do while smashing furniture.
- Yandere: A clingy Mood-Swinger who will beat you up and trash your car (if not outright light it on fire) if you show any sign of not being into her.
Dr. Saperstein
Dr. Saperstein
"Yes, this all started as vengeance for my children, but the company is making money now. Why would I back off just because these nincompoops lie to me all the time?"
Played By: Henry Winkler
"You attack a Saperstein, you face my wrath. Be so sure about this, tiny Tom, that I will crush you like the bug you are."
Jean-Ralphio and Mona Lisa's father. He finds his layabout offspring to be a huge disappointment, yet he is still very protective of them.
- Bunny-Ears Lawyer: Even while he's destroying their friend's life, Chris and Ann go to him for their pregnancy because he's that good.
- Doting Parent: He has no issue indulging all his kids' wishes and worst impulses even as he freely acknowledges how awful they are, especially Mona-Lisa.
- Extreme Doormat: Though he knows that his children are horrifically spoiled, he still hands Mona Lisa money whenever she demands it, largely because it's safer than denying her what she wants.
- Humble Parent, Spoiled Kids: Downplayed. While a mildly antagonistic force to Tom, the wealthy Dr. Saperstein is a fairly decent guy, in contrast to his Spoiled Brat children (whom he considers disappointments).
- Meaningful Name: His name is almost identical to the Satanist OB-GYN, Dr. Sapirstein, in Rosemary's Baby.
- My Girl Is Not a Slut: Is convinced Mona Lisa was a virgin before dating Tom; when he accuses Tom of stealing her virginity, everyone else in the room bursts into laughter at the idea.
- Nice Guy: Zig-zagged. He's got fantastic rapport with his patients and complains about being interrupted while watching Saturday morning cartoons with his son; but he loathes Tom over his perceived mistreatment of Jean-Ralphio and Mona Lisa to the point that he doesn't even care when he finds out that his kids were lying, and he makes it very clear that he considers his children to be complete and utter disappointments that he wants to offload at the earliest opportunity (although let's face it, the latter is entirely justified).
- Papa Wolf: Sets about destroying Tom's business because he believes Tom wronged Jean-Ralphio and Mona Lisa.
- Pushover Parents: He has spoiled his kids utterly rotten and just throws money at them whenever they ask for it.
- Screw the Rules, I Have Money!: After finding out that his kids lied about Tom's actions, he decides to continue with the business because it's making money.
- Serial Numbers Filed Off: In-universe, he opens a 'clothing rental store for teens' business just to run Tom's "Rent-a-Swag" out of business. It's so transparent that he even calls it "Tommy's Closet".
- Sitcom Archnemesis: To Tom in Season 6.
- Wacky Parent, Serious Child: Inverted. He's the Serious Parent (a normal, composed obstetrician/gynecologist) to his sleazy, irresponsible Wacky Children, and is all the more frustrated for it.
The Newports
Nick Newport Sr.
Nick Newport, Sr.
Played By: Christopher Murray)
Former CEO of Sweetums, a candy corporation that owns half the town. Dies at the end of Season 4.
- Corrupt Corporate Executive: While he doesn't do much in the series' present day, he's noted to have not been a very ethical businessman.
- Do Wrong, Right: A weird case. In Pawnee: The Greatest Town in America, it's revealed that the Pawnee Sun, the local tabloid newspaper, was started by his youngest son, Cal, when he wasn't able to use the family jet to buy his girlfriend a scarf in South America. He proceeded to set up the Sun to spill the dirt on his family's inner machinations. In a subsequent letter, Nick actually encourages his family to keep doing all the crazy crap they want to, because as long as they are, it means the Sun is selling copies and Cal is actually earning his own money rather than just mooching off his dad. The letter then got printed in an issue of the ''Sun''.
- Informed Flaw: While he may well have been a scheming evil businessman earlier in life, characters act as though he is still this way in the show despite the fact that he is a disabled elderly vegetable as early as Season 2. He is particularly painted as the mastermind behind his son Bobby's bid for City Council in Season 4 even though he doesn't even physically show up in that season and is likely far too senile by that point to mastermind anything, and it is more likely his wife Jessica is the true brains by this point.
- Killed Off for Real: Dies towards the end of the fourth season.
- Jerkass: Definitely not a case of Like Father, Like Son.
- Living Prop: Despite being featured in several plots, he never actually does or says anything. Justified to a certain extent, as he's little more than a decrepit vegetable by the time the series rolls around.
- Meal Ticket: For Jessica Wicks.
Jessica Wicks
Jessica Wicks
Played By: Susan Yeagley
Nick Newport Sr.'s Gold Digger wife. Also a Rich Bitch. She takes over as the CEO of Sweetums after her husband's passing.
- Conspicuous Consumption: A hallmark of her homes and offices.
- Corrupt Corporate Executive: When she takes over for her husband. Her company does awful things, even resulting in deaths, and she fires Ben when Leslie criticizes them.
- Gold Digger: Marries the richest guy in town for his cash, although the amount of nude portraits of his old, frail body that she had commissioned suggests that she might have been physically attracted to him as well.
- Every Man Has His Price: "Leslie doesn't pay for my lifestyle, money does."
- Money Fetish: When she announced the sale of the Newport land to Gryzzl in season 7, she repeated how much it was worth because "it makes me very horny."
- Obfuscating Stupidity: She acts like a very vapid Brainless Beauty in her first appearance, but later seasons show that there is in fact a scheming businesswoman underneath that smile. Her dimwitted Beauty Queen persona from her past might well have been just that, a persona, as it was made perfectly clear that this is what usually wins at such events. While she is certainly shallow and amoral, she is more savvy and conniving than she first appears.
- Rich Bitch: Once she gets married, she uses her wealth to seize historical buildings and get her dimwitted step-son Bobby elected as a puppet councilman note .
- Trophy Wife: For Nick Newport, Sr., although given that he was almost a vegetable at the time of their marriage, this might be a Subversion.
- Wicked Pretentious: Vandalizes a historical building to remodel it to her tastes for a birthday party for her husband (who is barely even aware of what is going on), and garishly redecorates her home and offices with nude portraits of herself and her elderly husband.
Bobby Newport
Bobby Newport
"Hi, I'm Bobby Newport. My dad is friends with John Cougar Mellencamp. That's pretty cool."
Played By: Paul Rudd
"How about you quit running, then I win, but then I let you do all the work."
Leslie's opponent in the City Council race. A Manchild and Upper-Class Twit to the extreme, he's really only running to do something to make his father proud of him.
- Brainless Beauty: Very attractive, despite his utter lack of intelligence.
- Friendly Enemy: He's Leslie's opponent in the council race, but he's incredibly pleasant and friendly towards her regardless — if only because he's apparently too dim to be otherwise. Towards the end of the campaign, he publicly endorses her, although he doesn't seem to realize the implications of that.
- Idle Rich: Runs for City Council to cast off these accusations... which are incredibly true.
- Lowest Common Denominator: In-Universe, he gets a lot of mileage in the campaign by spouting vaguely positive gibberish. It doesn't offend anybody because it doesn't mean anything.
- Manchild: Unlike most examples where the character is just incredibly immature, Bobby has so little understanding of how the world works that he often reacts like a child would.
- Nice Guy: He's actually very kind and generous, if only because he's too dumb to have a mean bone in his body.
- He's also the first one to applaud when Leslie gives a great speech, tells her how great it was, and votes for Leslie in the election. He apparently thinks you're not allowed to vote for yourself, but you can't help but feel that he's such a nice guy that he'd have voted for her anyway. Once he loses the election his only reaction is joy at the campaign being over.
- Pair the Spares: Ends up married to Shauna Mulwae-Tweep in a flash-forward in the Grand Finale.
- Puppet King: He does little in the way of actually opposing Leslie, leaving all of his campaign decisions up to Jennifer. He even offers Leslie the chance to do the City Council work for him if she lets him win the seat.
- Screw the Rules, I Have Money!: Throws money at any problem he comes across.
- Sheltered Aristocrat: He comes from major money. He's had so little exposure to the world that he generally acts more like a curious four-year-old than he does a man pushing forty. At the start of the election campaign, he is genuinely mystified as to why Leslie won't just let him win. Yet he is not at all malicious.
- Spoiled Sweet: Rare male example. He's not a jerk or even really a bad person in anyway, he just is so used to everyone giving him what he wants he doesn't understand why life doesn't always work that way.
- Upper-Class Twit: Is the richest man in town and is dumber than a brick.
- "Well Done, Son" Guy: The whole reason he ran for city council was to do something to prove to his father that he could accomplish something.
Nick Newport Jr.
Nick Newport, Jr.
Played By: Gary Weeks
Current CEO of Sweetums in Season 2 (until Jessica Wicks replaced him). Father of Denver (Ryan Hartwig) and Dakota (Harley Graham). As of Season 4, he seems to have been Retconned out of existence.
- Chuck Cunningham Syndrome: Apparently quietly retconned out of existence.
