12 Obscenely Wealthy Characters Who Get a Free Pass

Spoilers

Television sure enjoys spreading the wealth!

Many TV characters appear financially well-off, even adjusting for the fictional deflation of settings like Monica’s huge NYC apartment on Friends.

However, supremely rich TV characters are a bit thinner on the ground and usually painted as villains.

Don’t Hate Them (Just) Because They’re Rich

Related: Quit Your Day Job: What 11 Stars Did Before Making it Big

These moneybag characters often deserve their despicable reps, but some are so captivating that we’ll forgive them for almost anything.

Good Morning, Ted - Ted Lasso Season 3 Episode 12

The intrepid TV Fanatic team came up with a dozen excellent examples of wealthy characters who fit this bill and found that they fall into four main categories.

“Life of the Party”

These characters use their hard-won (or hard-inherited) fortunes to enjoy their lives unapologetically.

They typically display a sharp sense of humor and affect a jaded worldview that often masks a deeply sensitive (and therefore vulnerable) nature. 

Roger Sterling, Mad Men (AMC)

Roger Sterling Vertical - Mad Men

This impossibly cool and acerbic 1960s advertising agency scion wore his privilege lightly and always had a drink (usually vodka rocks) in hand.

His WWII service kinda balanced out other problematic tendencies, but Sterling’s sense of humor kept us from writing his character off completely.

He’s also the only Mad Men character who could wrangle a smile out of BFF Don Draper.

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Sterling’s money went into the ad agency, his impeccably tailored suits, and buying drinks for much younger women.

He was also incredibly astute and world-weary. That sense of pathos under everything he said makes forgiveness for this wealthy and flawed character not just possible but easy.

What can we say? Being a funny smartass covers a multitude of sins.

Maximo Gallardo Vertical - Acapulco S03

Maximo Gallardo, Acapulco (Apple TV+)

Maximo’s rags-to-riches story takes place mainly through the lens of his candy-colored 1980s youth, but his present-day self enjoys owning private jets and mansions on the southern California coast.

Young Maximo was ambitious, funny, and sweet. In middle age, he bears the mark of heartbreak and regret while simultaneously reveling in the sensual pleasures his money allows him.

He had questionable role models in his youth and tried to balance his mother’s strict Catholic teachings with his employers’ cutthroat business lessons that enabled his present wealth.

Maximo and Sara Receive News - Tall

Maximo exhibits many blind spots as he waxes nostalgic about his youth to his nephew while being a nightmare employer to his current staff.

However, his self-effacing humor and charm go a long way toward making his character sympathetic rather than insufferable.

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Deborah Vance, Hacks (Max)

The very definition of clawing your way to the top, legendary comedian Deborah Vance enjoys an obscenely comfortable existence in Las Vegas and doesn’t think twice about ordering artificial snow for a Christmas party at her mansion.

She also uses her private jet like an Uber and spends a fortune on vintage salt and pepper shakers.

Deborah Vance Updo Vertical - S03 - Hacks

The painful history fueling her comedy keeps her trapped in destructive patterns.

She uses her money to punish those who have wronged her without considering different courses of action.

Deborah isn’t naturally sympathetic or even particularly fair, but she can eventually recognize her wrongs and grudgingly make them right.

She’s also incredibly funny, experienced, and wise.

Rebecca Welton, Ted Lasso (Apple TV+)

Rebecca Prepares for a Showdown - Ted Lasso

On Ted Lasso, Rebecca is the new owner of AFC Richmond and received the bulk of her fortune from an acrimonious divorce.

She used her money at first in an elaborate evil scheme to undermine her hated ex-husband’s favorite football team.

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However, this plan backfired (in a good way) and restored her exceptionally kind and generous nature. She also gives to charity and helps her friends when they need anything.

Rebecca slowly healed after her divorce and visibly took pleasure in living again.

Her sense of humor returned, and she mended relationships with friends and family that she’d neglected during her lousy marriage.

Karen Walker, Will & Grace (ABC)

Karen Walker Vertical - Will & Grace

Will and Grace’s Karen was an incredibly wealthy wife, divorcee, and widow who no longer knew how non-wealthy people lived.

She was often thoughtless and cruel with her money and constantly popped pills of various types.

Her redeeming qualities were her loyalty to her friends, her sharp wit, and her enthusiasm for madcap adventures.

She was a frustrating character but also compulsively watchable and an audience favorite.

Bertha Russell, The Gilded Age (Max)

Mrs. Russell Descends - The Gilded Age  Season 1 Episode 9

Bertha, the nouveau riche wife of a railroad tycoon, luxuriates in her unfathomable wealth by conspicuously enjoying the best in fashion and interior design.

But she also puts her fortune to work, using it (and a little blackmail) to secure the social future of her children and establish the Russells as more powerful than even Old Money families like the Astors.

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Bertha loves it when a fancy party doubles as a cutthroat snub, but she really appreciates the elegant trappings of her position for their beauty on The Gilded Age.

She’s worked hard to maintain her family’s standing and is fiercely devoted to them. 

“Inheritance: Responsible”

Molly Novak Bow - Loot S01

These characters have been blessed by huge windfalls due to death, divorce, or the lottery, and they try to use this money to improve the world.

They are not always successful, and their contributions often cause more problems than they solve, but they share a sincere wish to use their newfound wealth for the greater good.

Molly Novak, Loot (Apple TV+)

Molly Novak got $87 Billion in her divorce from her husband and shifted her focus to working with the charity she founded and funded but forgot about for a while.

She’s very generous and, for a while, is pretty unapologetic about having money and spending it.

Molly Novak Vertical - Loot S01

But she also liked using it to care for others and admits that billionaires shouldn’t exist. Her focus now is on spending all her money on philanthropic work and real change.

Twyla Sands, Schitt’s Creek (Netflix)

Twyla is the ditzy but kind waitress-manager of Cafe Tropical who is always ready to lend a sympathetic ear and mix up your order.

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She won the lottery and has millions, but no one knows because she lives an ordinary and humble life.

We only find out because she chooses to give money to her friend Alexis Rose so she can follow her dreams.

Twyla Sands Vertical - Schitt's Creek

Twyla eventually uses some of her winnings to buy the restaurant and renames it Twyla’s Cafe Tropical.

“Inheritance: Clueless”

These characters prove that money doesn’t change you; it just makes you more of who you are.

Lucille Bluth, Arrested Development (Fox)

The matriarch of the Bluth family, Lucille is an alcoholic elitist who enjoys manipulating everyone around her.

She is blithely unconcerned with anything that doesn’t directly have to do with her.

Lucille Bluth Vertical - Arrested Development

Lucille doesn’t get a pass from her family but is beloved by viewers for her genius at roasting her kids.

She might’ve been a bad mom, but at least she was funny about it!

Mr. Burns, The Simpsons (Fox)

For an evil rich guy, Charles Montgomery “Monty” Burns from The Simpsons is almost completely powerless in his personal life and completely dependent on Smithers in his professional life.

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He is too old and simple-minded to be genuinely evil and borders on likability sometimes.

Mr. Burns is proof that a wealthy character’s cluelessness can bring them full circle from conscious malice to inadvertent decency.

The Caped Crusader Dark and Dashing

“Literal (Get Out of Jail) Free Pass”

These characters are pardoned by the law, usually by corrupt means, but viewers might still disapprove of their actions even if they can’t stop watching them.

Bruce Wayne, Multiple Batman TV Shows and Movies

I like Batman as much as the next person, especially the 1960s series with Adam West.

However, Bruce is a millionaire (or, depending on the show/movie, billionaire) philanthropist everyone seems to love.

Yet, by taking on the Batman persona and dealing with his brand of vigilante justice not only under the noses but with the approval (most of the time) of the police, he is showing a confident, above-the-law attitude.

George Clooney Looking Handsome

Both certain other characters (Alfred the Butler, Dick Grayson/Robin) and audiences seem to let him slide on that regularly and go along for the ride.

I would call playing a caped cop with no badge and no consequences getting a free pass.

Related: Gotham: Why You Should Love Batman’s Outrageously Fun TV Origin Story

Blake Carrington, Dynasty (ABC)

Blake is an oil tycoon and patriarch of the Carrington clan who got away with literal murder and several other crimes like covering up the adverse health impacts his oil company had on a community.

On top of that, when he was almost arrested for a bunch of crimes on Dynasty, including bribing politicians, he tried to frame his driver Culhane, who grew up in that community and whose dad died due to the health impacts.

Guilty or Innocent? - Dynasty Season 3 Episode 8

Blake’s daughter and Culhane were hooking up at the time, too, and Blake knew Culhane really liked her.

Blake also hid that they were related to another family, the Colbys, even when his daughter was having a romantic relationship with Jeff Colby. Neither of them knew.

What other wealthy characters do you think deserve a free pass?

Let us know in the comments below!

Paullette Gaudet is a staff writer for TV Fanatic. You can follow her on X.

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