11 Light-Hearted Comedies About the Wealthy and Their Antics

Get ready to dive into a world of luxury, laughter, and extravagant antics. We’re taking you on a whirlwind tour of ten sidesplitting lightweight comedies that revolve around the lives of the exceptionally wealthy. Having a lot of money can lead to plenty of absurd situations, and where there’s absurdity, there’s hilarity. From Crazy Rich Asians to Ruthless People, these 11 films about rich people are perfect for a hilarious light viewing that doesn’t take itself too seriously.

1. Crazy Rich Asians (2018)

Crazy Rich Asians (2018)
Image Credit: Warner Bros. Pictures.

This uproarious romantic comedy follows the whirlwind love story of Rachel Chu (Constance Wu) and Nick Young (Henry Golding). When Rachel accompanies Nick to his hometown of Singapore for his best friend’s wedding, she discovers that he comes from an outrageously wealthy family.

As Rachel navigates through extravagant lifestyles and demanding social circles, she must also contend with Nick’s disapproving mother (Michelle Yeoh) and a host of quirky and over-the-top characters. Packed with dazzling visuals, witty banter, and a heartwarming tale of love and acceptance, Crazy Rich Asians is a riotous celebration of love, family, and the hilarious absurdities of the super-rich.

2. Pretty Woman (1990)

Pretty Woman (1990)
Image Credit: Buena Vista Pictures Distribution.

In this beloved classic, Julia Roberts stars as Vivian Ward, a vivacious and street-smart prostitute who encounters Edward Lewis (Richard Gere), a wealthy businessman, while doing her job on Hollywood Boulevard. When Edward hires Vivian to accompany him to social events as his “date,” an unlikely connection forms between them.

As Vivian experiences a world of luxury and privilege, she teaches Edward to loosen up and appreciate the simple pleasures in life. With its memorable scenes, iconic fashion moments, and the irresistible chemistry between Roberts and Gere, Pretty Woman is a hilarious and unconventionally heartwarming tale of love transcending societal barriers.

3. Trading Places (1983)

Trading Places (1983)
Image Credit: Paramount Pictures.

This comedic gem takes a satirical look at the lives of the rich and the less fortunate. The story revolves around two wealthy brokers, Louis Winthorpe III (Dan Aykroyd) and Billy Ray Valentine (Eddie Murphy), who are manipulated by two eccentric millionaires (Ralph Bellamy and Don Ameche) as part of a social experiment.

The millionaires swap Louis and Billy Ray’s societal positions, leading to hysterical results as the characters navigate unfamiliar worlds. Trading Places is a must-watch satire of wealth and power thanks to Murphy’s brilliant comedic timing and Aykroyd’s hilarious transformation.

4. Clueless (1995)

Clueless (1995)
Image Credit: Paramount Pictures.

This iconic ’90s comedy, loosely based on Jane Austen’s Emma, transports viewers to the glamorous world of Beverly Hills. Cher Horowitz (Alicia Silverstone), a rich and popular high school student, sets out to improve the lives of those around her through matchmaking and social maneuvering.

Cher learns valuable lessons about love, friendship, and self-discovery. Packed with witty dialogue, memorable fashion trends, and a lovable ensemble cast, Clueless remains a hilarious and endearing portrayal of the privileged teenage experience.

5. Overboard (1987)

Overboard (1987)
Image Credit: MGM/UA Distribution Co.

In this laugh-out-loud comedy, Kurt Russell plays Dean Proffitt, a blue-collar carpenter seeking revenge on a spoiled and entitled heiress, Joanna Stayton (Goldie Hawn). After Joanna falls off her yacht and suffers from amnesia, Dean seizes the opportunity to convince her that she is his wife and subjects her to a life of domestic duties.

As Joanna adapts to her new life, she discovers the joys and challenges of working-class existence. With Russell and Hawn’s comedic chemistry and a heartwarming story of personal growth, Overboard delivers plenty of hilarious moments while offering a touching exploration of class dynamics.

6. The Bling Ring (2013)

The Bling Ring (2013)
Image Credit: FilmNation Entertainment.

Based on actual events, this dark comedy-drama dives into the lives of a group of fame-obsessed teenagers who embark on a spree of burglaries targeting the homes of wealthy celebrities. Led by Rebecca (Katie Chang) and influenced by their desires for fame and fortune, the group steals luxury goods while indulging in a glamorous lifestyle.

Directed by Sofia Coppola, The Bling Ring offers a satirical commentary on our celebrity-obsessed culture and the lengths people will go to experience a taste of the rich and famous. With its stylish visuals, gripping performances, and a blend of comedy and drama, the film explores the dark side of wealth and the consequences of unchecked ambition.

7. Weekend at Bernie’s (1989)

Weekend at Bernie's (1989)
Image Credit: 20th Century Fox.

This hilarious, offbeat comedy follows the misadventures of Larry Wilson (Andrew McCarthy) and Richard Parker (Jonathan Silverman), two young employees who discover that their boss, Bernie Lomax (Terry Kiser), has been murdered.

Instead of reporting the crime, they pretend that Bernie is alive and party it up at his luxurious beach house. As they navigate a weekend of deception and absurd situations, including Bernie’s body being mistaken for a dancing puppet, Larry and Richard find themselves in increasingly hilarious and precarious scenarios.

8. Taking Care of Business (1990)

Taking Care of Business (1990)
Image Credit: Buena Vista Pictures Distribution.

In this light-hearted comedy, Jimmy Dworski (James Belushi), a lowly ticket scalper, comes across a lost Filofax that belongs to wealthy and successful executive Spencer Barnes (Charles Grodin). Armed with the Filofax and newfound confidence, Jimmy bluffs his way into a high-powered business convention and assumes Spencer’s identity.

As he navigates through corporate challenges and encounters a love interest (Loryn Locklin), Jimmy’s comedic misadventures bring him face-to-face with the ridiculousness of the corporate world.

9. Dirty Rotten Scoundrels (1983)

Dirty Rotten Scoundrels (1983)
Image Credit: Orion Pictures.

Set in the glamorous world of the French Riviera, Dirty Rotten Scoundrels tells the story of two con artists: Lawrence Jamieson (Michael Caine) and Freddy Benson (Steve Martin). Lawrence, an experienced and sophisticated swindler, takes Freddy under his wing, but their relationship becomes competitive when they target the same wealthy woman.

A battle of wits ensues as Lawrence and Freddy engage in a series of hilarious schemes and elaborate cons to outwit each other. With Caine and Martin’s impeccable comedic timing, brilliant performances, and cleverly crafted plot, Dirty Rotten Scoundrels is a delightful comedy that showcases the art of deception and the absurdity of the rich and gullible.

10. Ruthless People (1986)

Ruthless People (1986)
Image Credit: Buena Vista Distribution.

This dark comedy centers around Sam Stone (Danny DeVito), a ruthless and wealthy businessman, and his unhappy wife, Barbara (Bette Midler). When a bumbling couple kidnaps Barbara (Judge Reinhold and Helen Slater), who mistakenly believe Sam wants her dead, Sam sees an opportunity to get rid of his wife and avoid paying a hefty ransom.

As the kidnappers’ plans hilariously go awry and Barbara discovers her inner strength, Ruthless People takes viewers on a wild ride filled with outrageous situations, sharp dialogue, and a twisted sense of humor. With its stellar cast and a story that subverts expectations, Ruthless People is a darkly funny comedy that skewers the excesses of the wealthy with unrelenting hilarity.

11. Parasite (2019) 

Parasite Universal Pictures
Photo Credit: Universal Pictures

This South Korean gem of a film, directed by Bong Joon Ho, is a twisty story. It centers on the destitute Kim family who live in the basement but craft a plan to con their way into employment at a wealthy family’s home, taking care of them. The film addresses class differences and greed through dark humor as the poor and wealthy families become each others’ parasites. 

Source: Reddit.

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       This article was produced and syndicated by The Cents of Money.

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