5 Most Famous Side Chicks Of All Time

5-Most-Famous-Side-Chicks-Of-All-TimeAs long as there’s been marriage, there have been affairs. Come on, every man and woman in a committed, long-term, monogamous relationship has wandering eyes occasionally. If that’s where the line is drawn, then no harm done. Sometimes, though, some of these members of a couple can’t help but take things a step further and get a little side action when they get the chance.
We are especially aware of affairs when a famous actor, musician, or political figure has found himself a secret side chick. Call me optimistic, but I think the paparazzi are getting better at their job. Anyway, some of these second squeezes tend to make history when they hook up with a guy in the spotlight. So let’s take a look at some of the more well-known mistresses in recent history (with one throw-back for perspective).


Famous Side Chick #5 – Anne Boleyn

Let’s start off with the historical one. Probably the most famous mistress of all time, Anne Boleyn single-handedly split the Church when Henry VIII wanted to marry her and formed the Anglican Church of England just so he could divorce Catherine of Aragon. Understandably, Anne Boleyn just wanted to stay Henry VIII’s side chick, rather than cause all the political drama that ended up ensuing anyway. Ironically, a short time down the road she was executed for allegedly having affairs of her own. Henry VIII’s love life continued to spiral afterwards as none of his wives would give him the male heir he desired. Kind of a crappy ending for both of them, but hey, at least Anne and Henry’s daughter continued on to become Queen Elizabeth I.

Famous Side Chick #4 – Ashley Dupré

In the early 2000s, Ashely Dupré was (to put it bluntly) a terrible singer, so she worked as an escort on the side to pay her rent since her music career wasn’t really panning out. It just so happened that one of her clients was Eliot Spitzer, the governor of New York at the time. The scandal broke in 2008, and both Ashley and the governor found themselves under a spotlight. The governor ended up resigning in disgrace, but Ashley actually saw a short climb in her music career following the incident. But hey, it doesn’t seem like it was enough for her, unfortunately. Name a song by Ashley Dupré. Go on. I’ll wait. VIDEO: Watch Ashley Dupre’s music video here

Famous Side Chick #3 – Rachel Uchitel

As the most recent affair on this list, you may already know about Rachel Uchitel and her single-handed destruction of Tiger Woods’ brand and ensuing game. In Melbourne in 2009, she and Tiger Woods were caught in some compromising sexual positions. You’d think this is bad enough, but Tiger’s wife, Elin Nordegren, was staying there with him. Not wise, Tiger. They were caught, Elin grabbed one of Tiger’s golf clubs and started beating him with it (no, really) and Rachel Uchitel became a millionaire overnight just to keep quiet about the affair. (Read about Rachel returning her hush money To Tiger Woods) Tiger’s life pretty much fell apart after that, and he can’t even play gold worth a damn anymore. But hey, I guess for some men, a certain woman is worth all that pain.

Famous Side Chick #2 – Marilyn Monroe

No list of famous mistresses would be complete with Marilyn Monroe. The rumors of her affair the President John F. Kennedy have never been substantiated, but the evidence is well-known and compelling enough for the affair to go down in legend anyway. JFK was a known playboy, and the rumors of his tryst with Marilyn Monroe were started or strengthened by her rendition of “Happy Birthday Mr. President” at Madison Square Garden. Unfortunately, this story doesn’t end well for either of them. Marilyn Monroe died under fairly suspicious circumstances in 1962 and President Kennedy was sadly shot and killed in 1963. In Marilyn’s case, this alleged tryst didn’t actually affect her career as much as you’d think since she was already a permanent member of every American man’s erotic dreams at the time. On top of that, she was never one to shy away from a little notoriety anyway. no matter what, you could just not beat her endless well of straight-up class.

Famous Side Chick #1 – Monica Lewinsky

Let’s fast forward a few centuries to the Clinton administration. In 1995 and 1996, White House intern Monica Lewinsky and POTUS Bill Clinton were having an affair behind Hillary’s back. Long story short, word got out and Clinton denied every allegation. She was called in to testify under oath, however, and ended up revealing that the entire affair was true. This led to an impeachment trial that did not end well for ol’ Slick Willy. Monica Lewinsky became a minor celebrity afterwards, though now she lives in the UK with much less infamy attached to her name.

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