10 Most Ironically Cast Movies Of All Time

As we all know, many movies are ironically cast at the outset simply to showcase an actor’s diversity or to make some larger point. Examples in this league include Charlize Theron as a grotesque killer in Monster and Brad Pitt as a slummy, badass in Fight Club. However, some movies don’t reveal their ironies until many months or even years after an initial release. These cases are not only intriguing on their face value, but they sometimes make it seem like the movie itself has a role in determining the actor’s fate.
Below is a list of the top 10 most ironically cast movies, specific to those ironies realized only in hindsight, of all time. Note: Not listed in any particular order.

1. Elizabeth Berkley - Showgirls

Basic Premise: Showgirls chronicles the rise of aspiring dancer Nomi Malone (Berkley) as she claws her way to the top of the showgirl ladder. After drifting into Vegas and working at some fairly undesirable establishments, Nomi scores a big audition. A few backstabs later, she’s a bonafide headliner. But in the end, she realizes that showgirl stardom may not be worth the questionable morals she has developed, so she heads to Hollywood where good morals and big success await her!
The Irony: Aside from the obvious irony of Saved by the Bell good girl Jessie Spano taking to the stripper pole, the real twist on this story is the parallel between Nomi and Ms. Berkley. While Nomi Malone achieves major success in Vegas and is presumably on her way to the success in Hollywood, the film demolished Ms. Berkley’s own aspirations: her acting career has yet to recover.

2. Winona Ryder and Angelina Jolie - Girl, Interrupted

Basic Premise: In Girl, Interrupted, recent high school graduate Susanna Kayson (Ryder) is checked into a pysch hospital after a failed suicide attempt. In the course of her stay, she befriends fellow patient and diagnosed sociopath, Lisa (Jolie), who encourages Susanna to break all of the rules. By the end of the film, Susanna, having learned a lot about life from her fellow inmates, checks out of the facility while Lisa just plain checks out.
The Irony: What’s interesting here is that both characters now seem ironically cast, but for opposite reasons. While Ryder’s character, Susanna, recovers from her depression and goes onto pursue a successful writing career, Ryder herself has become a bit of a headline-making nutjob after her arrest for shoplifting at Saks Fifth Avenue. In contrast, while the character of Lisa devolves into a mental breakdown, Jolie has become the poster child of motherhood and world peace, raising six children with partner Brad Pitt and working as a UN Goodwill Ambassador.

3. Eddie Murphy - Daddy Day Care

Basic Premise: In Daddy Day Care, Eddie Murphy stars as a father who opens a day care center after he’s laid-off from his high-powered job. Initially, he starts the day care to earn extra money but by the end of the film he turns down a more lucrative job when he realizes that he prefers spending time with the kids.
The Irony: The premise of Daddy Day Care couldn’t be further from the real life story of Eddie Murphy. After a relationship with former Spice Girl Melanie Brown led to Brown giving birth to a baby girl, Murphy refused to acknowledge paternity. Amazingly, this very un-fatherly behavior continued even after DNA evidence concluded that Murphy was indeed the father.

4. Lindsay Lohan - Mean Girls

Basic Premise: Lohan made a name for herself in Mean Girls when she tangled with some mean high school vixens. In the movie, Lohan’s character, Cady, spends her Junior year in a typical American high school after a childhood in Africa with zoologist parents. After initially gaining acceptance from the school’s reigning queen of mean, Regina, the two soon butt heads over a studly boy. Cattiness and backstabbing ensue until a full-on war erupts between the girls, ultimately leaving Cady as the new Queen Bee.
The Irony: Ironically, Lohan, whose role fighting other women in this film shot her to fame, would later make news for her unique love of women. She shocked everyone when she began seriously dating girlfriend Samantha Ronson in 2008. I wonder if Tina Fey, the creator of Mean Girls, has plans to write their sex scenes.

5. Liz Taylor - Father of the Bride (1950)

Basic Premise: An oldie but a goodie, Father of the Bride stars Liz Taylor as a blushing bride whose father has trouble coping with all of the disasters that occur between the time she announces her engagement and walks down aisle. But she does eventually walk down the aisle, and then it’s on her way to happily ever after with her one true love.
The Irony: This 1950 film became a classic tale of inspiration for brides-to-be of all ages. It was so popular that it was remade in 1991, starring Steve Martin as the unlucky father of the bride. In real life, however, Ms. Taylor has become a cautionary tale to women everywhere after walking down the aisle an astounding 8 times! She must really like the Honeymoons, I suppose.

6. Hugh Grant - Pick any movie he was in

Basic Premise: Hugh Grant has a gift (or a typecast) for playing the charming, though putzy, lead in some of our most beloved romantic comedies - Four Weddings and Funeral, Mickey Blue Eyes, Notting Hill, Sense and Sensibility, About A Boy, Love Actually, just to name a few. The plotlines tend to go down the same path – Grant meets a girl, obstacles surface, he somehow fuddles through them, and, in the end, his unwavering sweetness wins the day and, of course, the girl.
The Irony: Unfortunately for Grant, his real life narrative has played out somewhat differently. Grant was arrested in 1995 for lewd conduct with a prostitute while dating British beauty Elizabeth Hurley – not very romantic. And although he’s never had a problem attracting the ladies, paid and non-paid alike, the confirmed bachelor has yet to find a storybook ending.

7. Tom Cruise - War of the Worlds

Basic Premise: In War of the Worlds, Tom Cruise saves planet Earth from total destruction by fighting foreign invaders from a distant planet. In the film, Cruise’s character, Ray, is taken off-guard by the invasion and struggles to figure out the pieces to the puzzle as the narrative evolves.
The Irony: After making the film, Cruise became infamous as a leading figure in the Scientology movement for, among other things, publicly denouncing the use of therapy to solve one’s mental and emotional ailments. Ironically, Scientology is a religion that believes extraterrestrial creatures live amongst us and must be expunged from the Earth. Think about it: Tom Cruise was playing a guy who unexpectedly battles aliens from a distant planet, but then publicly dedicates his real-life to battling the aliens within himself? That’s crazy on many levels.

8. Ben Affleck - Good Will Hunting

Basic Premise: Good Will Hunting is the classic story of a boy savant from Boston (played by Matt Damon) who struggles to accept his gift and take advantage of the opportunities his gift affords him. The film co-stars Ben Affleck as Will’s not-so-genius best friend who is ultimately left to a life of brick laying while Will goes off to pursue his destiny.
The Irony: The film (co-written by Damon and Affleck, who won Academy Awards for their script) should have been a launch pad for both their careers. But something a little different happened on the road from the Oscars. Damon went onto a genius career with roles in The Talented Mr. Ripley, The Departed, and the Oceans’ Eleven and Bourne series. Affleck, however, laid one brick after another with roles in films such as Changing Lanes, Jersey Girl, Man About Town and the biggest brick of all – Gigli. Sure, Affleck has made a ton of money, but money doesn’t buy integrity, does it? Wait… does it?

9. Bill Murray - The Royal Tenenbaums

Basic Premise: In The Royal Tenebaums, a story about a dysfunctional family, Murray plays neurologist Raleigh St Clair, the husband of Tenenbaum daughter Margot (played by Gwenyth Paltrow). Through the course of the film, Raleigh is neglected and ultimately cuckolded by his wife, whom he absolutely adores. At the end, Raleigh confronts Margot about her affairs, as well as her smoking habits, but to no avail.
The Irony: In the film, Raleigh stands out as a devoted and loving husband to the narcissistic Margot. He tries to keep her grounded while working diligently at his academic pursuits and is shocked to learn both of her affairs and smoking habits. In reality, sadly, Murray’s wife divorced the actor in early 2008, citing spousal abuse as well as drug and alcohol addiction. Talk about the flip side of the coin, huh?

10. Demi Moore - Indecent Proposal

Basic Premise: In this hugely successful early 90s drama, Diana and David Murphy (played Demi Moore and Woody Harrelson) are down on their luck and in desperate need of cash. They head to Vegas in a vain attempt to win big, but wind up losing big instead. When an older multi-millionaire, John Gage, (played by Robert Redford) offers them one million dollars for a night with Diana, they debate the proposal at first but eventually accept. Then, although one million dollars richer, they are wracked with jealousy and mistrust, their marriage hits the rocks, and Diana leaves David for the older Mr. Gage. In the end, however, Diana decides that Mr. Gage is not her true love, and she soon returns to the more age-appropriate David.
The Irony: Who could have predicted that twelve years after Indecent Proposal hit theaters, Demi would find herself part of a real life couple that’s notable for their age disparity. In 2005, Demi married Ashton Kutcher, 16 years her junior. Let’s hope Ashton doesn’t try to sell a night with Demi on eBay.

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