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Mistresses have intrigued generations of scandal-thirsty people since the beginning of forever. For centuries, legendary side-pieces ranging from Cleopatra to Olivia Pope have been celebrated despite their famously-filthy ways. Hate em or love em, these infamous side-chicks will always be relevant.

Here are the 15 most infamous mistresses of all-time. Take a look.

Marilyn Monroe

The widely-beloved bed-hopper was President Kennedy’s mistress between slorey-conquests with his brother and several star athletes. On a scale of Olivia Pope to 10, she’s a strong 11.

Alicia “Off” Keys

Everyone loved A. Keys and her handy-dandy piano before she slithered away with a married woman’s husband and unleashed her wrath upon humanity with “Girl On Fire.” Top 5 most hated homewreckers alive? It’s possible.

Monica Lewinsky

The super-freaky intern crept around with ex-president Bill Clinton in the mid-’90s and later alleged that they had 9 sexual encounters together. Two years later, Clinton admitted his inappropriate relationship with Lewinsky who turned into a walking punchline. The infamous love-juice stained dress…and cigar. Bill nasty.

Angelina Jolie

The puffy-lipped “free-spirit” is easily the most famous homewrecker in Hollywood and it’s never hurt her career. According to legend, she stole Brad Bitt from the homely Jennifer Aniston while filming “Mr. & Mrs. Smith,” adopted thousands of kids with him and lived happily ever after. Jennifer, on the other hand, never recovered.

Sahel Kazemi

According to police, the deranged mistress of NFL legend Steve McNair shot him twice in the head, twice more in the chest, then pressed the gun against his temple for the last shot before turning the 9mm semi-automatic pistol on herself. Saddest real-life episode of “Snapped” ever.

Lil Kim

More known for her plethora of Asian Muppet faces than her infamous affair with Biggie (who was married to Faith), Liddo Kimmy’s entire career has been filled with nothing but scandal, melting faces and filth.

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Lauryn Hill

The tax-allergic master priestess of fake-deepery was Wyclef’s mistress on the low and soon went completely-insane. Pras? Always in the middle of the dysfunctional lovers, hoping for a reunion.

Gabrielle Union

Dwyane Wade’s snobby side-chick-turned-girlfriend allegedly stole the Heat All-star from his trashy ex-wife Siohvaughn Funches who sued her (unsuccessfully). Now Gabby lets him leave the house dressed like an Erykah Badu victim.

Kim Zolciak

Remember “Big Poppa?” Yea, he was married and Kim was his mistress.

Katelyn Faber

That infamous night in Colorado that almost ruined Kobe’s life…..


All Tasia Mae’s career she hadsta fight. Chronic illiteracy, keeping her shoes on, watching her doomed relationship with a married man crumble, it’s been rough, but somehow she made it through. Kinda.

Vanessa Lopez

The notorious scuzzbucket was linked to several NBA players including Shaquille O’Neal who smashed behind ex-wife Shaunie’s back until the fame-thirsty parasite attempted to extort millions from him.


The irrelevant singer and her furry-sideburns could usually be found in Irv Gotti’s bed at the height of Murder Inc.’s run. Could that be the reason Nelly never wifed her? Hmm…

Rachel Uchitel

The VIP club hostess was the first (and most famous) of Tiger Woods’ mistresses to be exposed (and exploited) by the media. Her instant fame lasted exactly 15 min. and peaked with her stint on “Celebrity Rehab.”

Rielle Hunter

The low-key slorey filmmaker met then-Democratic presidential candidate John Edwards in 2007 when she was hired to make promo videos for his 2008 campaign. Soon, more than videos were made and she ended up knocked up and disgraced. Note: John Edwards’ wife was battling cancer during the affair.


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