15 Biggest Male Gold Diggers In Hollywood That Clearly Have No Shame

Usually, when we talk about gold diggers, we are referring to women who go after rich men. But it’s not always women that are digging for gold — Hollywood is full of men who are just as willing to go after money as some women are.

The term is typically applied to women, but you might be surprised how many men are out there riding the gravy train. They can be just a slick in wooing a rich lady as the women are at flirting with loaded men, and sometimes, they are even better at it. They are obviously after money and they will look for women who are more modest and not arrogant. If you look closely enough, you will see them all over Hollywood. A male gold digger can be found anywhere, but in this case, we will focus on the Hollywood gold diggers that clearly have no shame.

In some cases, men will look for women who are insecure; they manipulate their need for a man in their life that dotes on them and then the next thing you know, that guy is on easy street. You can imagine how many options they have in Hollywood because the industry is filled with insecure models and actors. Insecure women are usually prime targets for situations like this, but it’s also not always the case. Check out 15 of the biggest male gold diggers in Hollywood who clearly have no shame.

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15 Raffaello Follieri Took Us By Surprise

Seriously, how did these two even meet? When it came to the lovely Anne Hathaway, we always assumed that she would marry someone in the industry since that’s what typically happens. Anne Hathaway dodged a bullet with this one because he probably had plans to take her to the cleaners. The two were together for four years and many assumed that they would get married.

That was until Follieri was arrested for embezzling $50 million from billionaire Ronald Burke as well as the Roman Catholic Church.

When the scandal broke, Hathaway immediately broke up with him because she was worried that the scandal would affect her career. Follieri was deported from the United States and thrown in an Italian prison. There is no telling how much he would have embezzled from Hathaway if he had been given a chance.

14 Guy Ritchie Got Wealthy

US singer Madonna (L) and her husband British director Guy Ritchie pose as they arrive to attend the screening of Nathan Rissman's film 'I Am Beacuse We Are' at the 61st Cannes International Film Festival on May 21, 2008 in Cannes, southern France. The May 14-25 festival winds up with the awards ceremony for the prestigious Palme d'Or, to be determined by a jury headed by Hollywood "bad boy" Sean Penn. AFP PHOTO / ANNE-CHRISTINE POUJOULAT (Photo credit should read ANNE-CHRISTINE POUJOULAT/AFP/GettyImages)

Guy Ritchie married the queen of pop, Madonna and he went from being successful to being quite wealthy. He was probably doing alright before he met her, but she sure put him on a whole new level. Ritchie was a director before he met Madonna and when they divorced, he became quite the rich man. She was the one that had to pay him in the end. They were married for a fairly long time, eight years, by Hollywood standards.

When they got divorced, Ritchie received a settlement that was quite large, between $76 and $92 million dollars.

That’s quite the chunk of change for eight years. Ritchie only has good things to say about his marriage to Madonna. He was quoted as saying that their marriage was “ultimately very positive.” Yeah, we bet.

13 Dean McDermott Went For The Rich Girl

Dean McDermott was virtually unknown before he met Tori Spelling on the set of Mind Over Murder. Not only was he a struggling actor at the time but he was also married. When he met Tori Spelling, it’s likely that he saw a meal ticket to an easier life. It didn’t take much for him to leave his wife. They were in the process of adopting a child.

He may have thought at the time that she was getting a huge inheritance from her father’s $500 million estate,

but it turns out that Tori Spelling’s share of the estate is only $800,000. That’s a shockingly low inheritance, but we all know that her mother took the lion’s share of the estate and isn’t much for sharing.

12 Kris Humphries Saw A Gold Mine

Kim Kardashian has been married three times and her second marriage was to Kris Humphries. It was an odd match and it only lasted 72 days. The basketball player probably thought he would have more of a chance at her fortune than that.

But he had a hard time tolerating Kim’s family and sometimes, even Kim herself. He seemed to want to try to stick it out for as long as he could.

The Kardashian women certainly know how to make a lot of money. It’s not like Kris was a poor guy, basketball players make a good income as well, but nothing like the millions that Kim brings in. They divorced and Kim got together with someone a little more like her. Now, these two might actually stay together.

11 Matt Rutler Had His Eye On The Prize

Christina Aguilera has a habit of dating obscure men. Maybe she’s not into the Hollywood men because she seems to end up dating men that we wouldn’t normally see a mega-star with. Matt Rutler was just that — a nobody who just so happened to be at the right place at the right time. The two met on the set of Burlesque; she had the starring role in the movie while he was the production assistant. The two have been engaged now for a few years and share a child together named Summer. We’re sure his life completely changed when he moved into the singer’s $10 million mansion. Who knows, maybe they did genuinely fall in love? But he couldn’t have picked a richer girl to fall for. Aguilera is a fan of dating non-famous men.

10 Kevin Federline Saw His Golden Ticket

It must have been a dream come true for Kevin Federline to get a gig as one of the backup dancers on Britney Spears’ tours. She was at the height of her career then and it appeared as if she had the world at her feet. That was until she met and fell in love with Federline. We often wonder what these guys say and do to get rich and famous women to even look their way. Her heart may have still been tender from her breakup with Justin Timberlake because when she hooked up with Federline, it was all part of the many things that came together to sink her successful career. The divorce was probably what set off her mental breakdown and in the end, Federline ended up with custody of their two children and she pays him $20,000 a month in child support.

9 Nick Cannon Found His Pop Princess

Another weird celebrity matchup was Nick Cannon and Mariah Carey. It seemed so odd that someone of her wealth and fame would start dating a virtual nobody in the industry.

Sure, he’s an actor and a TV personality, but definitely not someone that is anywhere near her level of fame. He was doing alright in Hollywood before he met Mariah, but when the two got married, he might as well have gotten a tattoo that said “gold digger” because that’s how everyone saw him.

The two got married, had some babies, but it only lasted a few years. We’re not sure how much Nick Cannon got away with in the divorce settlement, but Mariah isn’t typically very generous with the men she leaves behind. She went on to date someone who was far wealthier than she was, but it doesn’t look like that panned out either.

8 Russell Brand Felt Love At First Sight

Or that was at least what he claimed when he first met Katy Perry. Before he met Perry, he was a recovering addict who had written a few memoirs and definitely had some millions of his own.

But that didn’t stop him from seeing the value of marrying someone like Perry.

They met when Perry filmed a hot cameo for Brand’s movie, Get Him to the Greek. That’s when the flirting started and before we all knew it, the two were married. That marriage, however, only lasted just over a year. He was the one that served her with divorce papers in 2011 and stated to the media that he still “loves Katy dearly,” but peaced out anyway. There was no prenup in their marriage, so Brand walked away with half of Perry’s income at $44 million.

7 Justin Theroux Found His Californian Blonde

Justin Theroux sure landed him a beauty when he met and got together with Jennifer Aniston. Not only is she super famous, but she has a lot of money as well. He was doing okay on his own before he met Aniston, but as soon as they started dating, it’s as if his career skyrocketed. We’re sure she had a lot of pull in the industry and was more than willing to help her man out. He was dating Heidi Bivens when he met Aniston and had no problem getting rid of that 14-year relationship so that he could pursue Aniston.

Many people thought that the relationship was a little too perfect for Theroux, and that Aniston was moving too fast.

The two got married and have only been married for a couple of years now. They just announced their split and although it’s too soon to know why, we are betting that Theroux thought it was time to move on to the next one.

6 Casper Smart Was The Backup Dancer

attends the The Weinstein Company's 2013 Golden Globe Awards after party presented by Chopard, HP, Laura Mercier, Lexus, Marie Claire, and Yucaipa Films held at The Old Trader Vic's at The Beverly Hilton Hotel on January 13, 2013 in Beverly Hills, California.

Jennifer Lopez could probably have any guy in the world as her husband, so it is often shocking to us when she hooks up with a backup dancer. Lopez got all hot and bothered with the much younger and hotter Casper Smart. She ended her seven-year marriage to Marc Anthony and took up with Smart. He’s 17 years younger than her, but he wasn’t complaining because he got promoted to being her choreographer and got a weekly allowance of $10,000 a week from the singer. Though we’re sure Lopez didn’t mind since she had a young guy with a super hot body.

The two eventually broke up, however, in the most scandalous of ways.

As if dating one of the hottest women on the planet wasn’t enough for Smart, he got tangled up in a scandal involving a transs*xual model.

5 Gabriel Aubry Found The Foxiest Woman In Hollywood

Halle Berry has never had much luck with love over the years and we’re not sure why. She’s insanely gorgeous and she has all the talent in the world. She met Gabriel Aubry who was a model at the time and the two got together. They were married and they also share a child together.

Aubry may have seen dollar signs when he married Berry because when they eventually divorced, things got nasty. He wanted $20,000 a month in child support so that he could provide his daughter with the same standard of living that she was used to when she was at her mom’s.

We’re sure that he was more worried about the lifestyle that he had come accustomed to. He ended up getting what he wanted and she was left with a bad taste in her mouth.

4 David Gest Was Super Creepy

We’re not sure where Liza Minelli found this guy, but he gave us the creeps from day one. At the time that he met Minelli, he was just a concert promoter, so we’re pretty sure he was looking for a very different kind of lifestyle. He was the type of guy that liked a lot of attention but didn’t have any talent to get him any.

They had a huge wedding that included Michael Jackson as the best man and Elizabeth Taylor as the maid of honor. Despite the elaborate wedding, the marriage only lasted two years.

That was when things really started to get ugly. We saw Gest’s true colors when he went after Minelli for $10 million, stating that the money was for damages caused to him. The case was dismissed when Minelli proved he was just after her money. He went back to obscurity and she kept all her millions.

3 Eric Johnson Found Himself A Rich Blonde

There is nothing better than marrying a super foxy blonde, that is unless she happens to be a very rich foxy blonde. Eric Johnson is a retired football player with his own handsome bank account, but he doesn’t mind one bit that Simpson is definitely the breadwinner in the family.

Sure, she may be a former singer and actress, but these days, Simpson is rocking out the entrepreneur lifestyle with a clothing brand, among other things.

They have two children now and we’re not really sure how Johnson fills his days aside from hanging out with his friends or playing with the kids. He’s certainly living the highlife now with the wealth that Simpson has accumulated over the years. These are situations where you hope there is a good prenup in place because in Hollywood thinks typically don’t last long.

2 Rossano Rubicondi Knows A Good Thing When He Sees It

We have to assume that Rossano Rubicondi was only dating Ivana Trump for her money. She has not aged well and it would not be the same as dating an older woman like Jennifer Aniston. She is the original Mrs. Trump and the mother of Trump’s children, or the older ones anyways. Rubicondi and Trump have a 23-year age difference between them. They were married for a time back in 2008 and we doubt it was love that got him to the altar.

The wedding cost a whopping $3 million and their marriage lasted only eight months.

Apparently, the two still hook up from time to time because why wouldn’t you sleep with a guy who is 23 years younger than you on the side. We bet there are other perks for him as well.

1 Helg Sgarbi Is The King Of Gold Diggers

We would have to say that Helg Sgarbi is the king of all male gold diggers. He was a former Swiss investment banker and he discovered that the way to wealth was through gullible, wealthy women.

One of his victims happened to be BMW heiress Susanne Klatten and she’s worth a stunning $9.6 billion. So, he wasn’t going after small potatoes.

He didn’t bother to try to marry these women and then take their money, he used the old-fashioned way — blackmailing. He would get involved with these women and then threaten to release the tapes. Since Klatten wasn’t interested in the same kind of fame that Kim Kardashian got, she decided to pay him off in the millions. He also got another $6 million from her for a faux-mafia tale. That doesn’t include the three other women that he managed to seduce for money. In Europe, they don’t take kindly to blackmail and they are even less impressed with threats of releasing tapes, so he was arrested and sentenced to six years in prison.


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