Scandals And Illicit Affairs: Hollywood's Best Kept Secret Affairs
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Scandals And Illicit Affairs: Hollywood’s Best Kept Secret Affairs Of All Time

If there’s anything that we have learned from Hollywood, then it’s the reality behind fairy tale endings and happily-ever-after stories – the truth that doesn’t always get portrayed. Celebrity couples spend so much time apart due to their hectic work schedules – spending time on different sets across the world with different irresistibly attractive colleagues is common.

And that friends happen to be the ingredients for stirring some major tea – illicit affairs, scandalous break-ups, and timeless love stories.

So we decided to look back at some of the best illicit affairs of all time – Hollywood’s best-kept secret affairs that sound shocking even today! Stay tuned to read about Hollywood’s most illicit affairs of all time.

Scandals And Illicit Affairs: Hollywood’s Best Kept Secret Affairs Of All Time

Welcome to Gossipment’s favorite illicit affairs from Hollywood! Today, we will talk about some of the most shocking cheating scandals of all time. Behind closed doors and tinted windows, who cheated with whom – which celebrity gave in to temptation, and which celebrity got cheated on? Scroll down to read about Hollywood’s best-kept secret affairs of all time!

1.Kristen Stewart With Rupert Sanders

Kristen Stewart With Rupert Sanders

When Twilight first hit big screens, fans across the globe blessed the reel-to-real-life couple, Robert Pattinson and Kristen Stewart. Everything was fine until Steward made some serious headlines in the month of July 2012 when she got a little too close to her Snow White & The Huntsman director, Rupert Sanders.

Sanders was married at the time, and the affair was doomed. Although Stewart apologized publicly to Pattinson later, and the two actors even resumed their relationship for a while, they were unable to stay together – the couple split officially later the same year.

2. Brad Pitt With Angelina Jolie

Brad Pitt With Angelina Jolie

Come on, you need not look for illicit affairs lyrics – instead, just look at Brad Pitt, Angelina Jolie, and their illicit affair. Pitt was happily married to Jennifer Aniston when he met Jolie on the sets of Mr. & Mrs. Smith. Pitt fell for Jolie, and by 2005, Aniston had filed for the inevitable divorce.

Although the Girl, Interrupted actress mentioned nothing happened until Pitt officially separated from Anniston yet, during a 2008 interview, she also claimed, “Not a lot of people get to see a movie where their parents fell in love.

3. Elizabeth Taylor With Richard Burton

Elizabeth Taylor With Richard Burton

Eddie Fisher was a married man in the 1950s. When Elizabeth Taylor’s husband, Mike Todd, died tragically in a plane crash, Fisher’s wife, Debbie Reynolds, reportedly asked her husband to be there for Fisher since he was friends with Taylor’s late husband. But this mutual grieving soon turned into a scandalous affair, especially when Fisher divorced Reynolds to marry Taylor.

Surprisingly, Taylor’s relationship with Fisher ended just how it started – with a scandalous affair. Taylor left Fisher for none other than Richard Burton, her co-star from Cleopatra – pretty scandalous, but Taylor’s marriage to Burton lasted for an entire decade. 

4. Ben Affleck With The Nanny (Christine Ouzounian)

Ben Affleck With The Nanny (Christine Ouzounian)

There’s no denying that Jennifer Garner and Ben Affleck had one of the dreamiest love stories of all time – but like all good things, even this one came to an end. While it was reported that there were several reasons behind the celebrity couple’s breakup, the strongest rumors that circulated were all about Affleck’s extramarital affair with the nanny, Christine Ouzounian. 

Why is it always the nanny? One of the juiciest illicit affairs of the time, the media only needed confirmation, and by 2016, they even had that when the 13 Going On 30 actor confirmed all the rumors.

5. Jada Pinkett Smith With August Alsina

Jada Pinkett Smith With August Alsina

Nah, you don’t need to look beyond ‘Taylor Swift illicit affairs’ – instead, you can just read about what happened to the Smiths. It was June 2020 when August Alsina first spoke about his relationship with Jada Pinkett Smith. He said,

“I totally gave myself to that relationship for years of my life, and I truly and really, really deeply love and have a ton of love for her.”

The world was shocked even more when Alsina also mentioned how Will Smith was aware of this relationship. Initially, the couple denied the relationship, but then Pinkett Smith appeared on the elusive Red Table. Yes, the Smiths had a dark period in their marriage when Jada did go out with Alsina before working things out with her husband.

6. Woody Allen With Soon Yi Previn

Woody Allen With Soon Yi Previn

You don’t need to find illicit affairs meaning to understand exactly how scandalous things got when Woody Allen’s affair with his ex-stepdaughter came under the spotlight. The Midnight In Paris director started an affair with Soon Yi Previn, the adoptive daughter of Mia Farrow, Allen’s longtime girlfriend.

The scandal came out into the open when Mia came across Previn’s nude photos, allegedly taken by Woody Allen. Although highly criticized, Allen still ended up marrying Previn sometime in 1997.

7. Marilyn Monroe With Arthur Miller

Marilyn Monroe With Arthur Miller

While Monroe and Miller were married eventually, how can anyone forget that it all inevitably started with an affair? When the blonde bombshell was married to Joe DiMaggio, Miller used his writing skills to send ‘lustful lover letters’ to Monroe. The year was 1954 when Monroe finally filed for divorce from DiMaggio. 

It was perhaps the biggest green signal for Miller, considering he immediately started to woo Monroe – he reportedly wrote her letters, begging her to just come back. Monroe obviously gave in and eventually married Miller.

8. Alex Rodriguez With Madonna

Alex Rodriguez With Madonna

Alex Rodriguez was married to Cynthia Scurtis when he started an affair with Madonna. It might not have been one of the biggest illicit affairs of all time, but the Like A Virgin singer and the Yankees player made hardly any efforts to hide their affair. Rodriguez ended up paying around 26 million dollars to Scurtis as a settlement.

People reported a source close to Cynthia Scurtis in 2008 saying,

“The embarrassment over Madonna was the last straw. She flew to Paris to get out of town before everything blew up between them.”

Gossipment’s Ode To More Tea (Bonus Section): Illicit Affairs And Scandals

Welcome to Gossipment’s bonus section! We decided to add a little twist to our list of Hollywood’s best-kept secret affairs. Interestingly, the illicit affairs of Hollywood are not just restricted to celebrities from the industry. How can we forget the Royals? So without wasting time, Here are the three most scandalous affairs of the Royals. 

1. Camilla Parker Bowles And Prince Charles:

Once Princess Diana’s affair became public, so did Prince Charles’ relationship with his current wife, Camilla Parker Bowles. In fact, an Australian magazine even published a transcript of the duo’s steamy bedtime conversations over the phone. 

The transcript very memorably features the pair discussing what it would actually be like in case Charles was to be Camilla’s tampon – really, guys! The scandal finally led to the end of Diana’s unhappy marriage to Charles. The then Prince of Wales (and now King of England) got married to Bowles in 2005.

2. Peter Townsend And Princess Margaret:

If you watched the earlier seasons of The Crown on Netflix, then chances are you already know where this one is going – back into the 90s when the former Queen of England’s sister Princess Margaret fell in love with a Royal Air Force officer, Peter Townsend! 

While the Queen approved of the relationship and even promised to help the pair, it wasn’t meant to be, resulting in the two getting involved in an affair while trying to hide it from everyone. 

The RAF officer spent a lot of time with the princess behind closed doors, even after he was married. While Townsend did leave his wife eventually for Maragret, the spotlight on the couple kept them apart from getting married ever. 

3. Mark Phillips And Heather Tonkin:

The former Queen of England has only one daughter, Princess Royal Anne, who went on to marry Mark Philips. While staying married to the only daughter of the Queen at the time, Philips actually fathered a lover child with Heather Tonkin, a woman from New Zealand. 

When news of the affair became public knowledge, it led to Anne getting divorced from Philips in 1989.

And It’s A Wrap!

And that’s a wrap on the most illicit affairs of all time – at least, our favorite Hollywood affairs of all time! What do you think about these affairs? Do you have some other exciting names inside your head? We would love to hear about some other scandalous stories that we might have missed out on here. Feel free to share your thoughts, other names we might have forgotten, and anything else really in the comments below – we’ll be waiting to hear back from you!

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Barsha Bhattacharya is a senior content writing executive. As a marketing enthusiast and professional for the past 4 years, writing is new to Barsha. And she is loving every bit of it. Her niches are marketing, lifestyle, wellness, travel and entertainment. Apart from writing, Barsha loves to travel, binge-watch, research conspiracy theories, Instagram and overthink.

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