Hollywood's Most UNDESIRABLE Bachelors — Ranked! From 'Skirt-Chasing Workaholic' Kevin Costner to Depp and DiCaprio

Horse-riding Yellowstone alum Kevin Costner is a single man again after a second disastrous divorce, and friends said the third time is NOT the charm for the actor, who’s lost a ton of hard-earned cash to his two ex-wives — and has circled the wagons against another masked bandit.

The 69-year-old The Bodyguard bachelor won big when a judge enforced his prenup with his second wife, Christine Baumgartner. But during his 1994 divorce from his first wife, Cindy Silva, mother of his three oldest kids, he got taken to the cleaners and was forced to hand over a staggering $80 million. They had no prenup.

He also has three kids with Baumgartner, who he wed in 2004, and a love child with New York Giants football heiress Bridget Rooney.

The handsome Dances with Wolves star has taken up with lots – and lots – of women, including supermodels Elle Macpherson and Cheryl Tiegs, newscaster Joan Lunden, Friends star Courteney Cox, and actresses Michelle Pfeiffer and Halle Berry.

Costner has said: "I’ve lived quite a colorful life."

Another problem with Studly Do-Right? He’s always busy – both of his wives say he’s a never-stays-home workaholic.

The 49-year-old A Star Is Born hunk has dated his fair share of gals, including Jennifer Lopez, Zoe Saldana, Suki Waterhouse and even Hillary Clinton’s aide, Huma Abedin, said insiders.

Bradley Cooper's only marriage, to Blue Bloods alum Jennifer Esposito, ended in 2007 after only a few months of matrimony.

In her memoir Jennifer’s Way, she said, "He was funny, smart, cocky, arrogant and a master manipulator. He had a mean, cold side — and his personality could flip on a dime."

Cooper's longest relationship was with baby mama model Irina Shayk, who still keeps him in her life even though she regularly dates other men since their 2015 breakup. He has been seen with model Gigi Hadid, but a source said he was keeping it "super casual." However, things have seemingly progressed as they have been photographed together several times.

He’s also a proud mama’s boy. Gloria Campano, who accompanied her son to this year’s Oscars – in matching outfits – is a big part of his life.

Jimmy Kimmel joked on stage at the awards ceremony: "It's very sweet. But the question is, how many times can one bring his mom as his date before he is actually dating his mom?"

The 56-year-old Ray star is afraid of commitment, according to insiders, who say he’s a serial skirt-chaser who cheated on America’s sweetheart, Katie Holmes, who he dated between 2013 and 2019.

While brokenhearted Holmes never publicly shamed her ex, the Oscar-winning actor — who survived a mysterious brush with death insiders said was a stroke — has never made any claims he’s going to be a faithful guy — to anyone ever!

Jamie Foxx wrote in his memoir, Act Like You Got Some Sense: "I’ve just never been convinced that marriage was a good idea for me.

"I’ve had friends that have great marriages, others not so much. And it never seemed like marriage was necessary."

The handsome actor has been linked to beauties like Vivica A. Fox and Clueless actress Stacey Dash. Kristin Grannis is mom to his 14-year-old daughter, Annalise. He also has daughter Corinne, 30, from another ex-girlfriend, Air Force veteran Connie Kline.

He said not marrying his baby mamas has made him a better dad.

What woman could trust the most beautiful man on the planet? Just ask Brad Pitt’s first wife, Jennifer Aniston.

Pitt radiates charm and humor, but you’d have to send him out with armed guards every time he went for a gallon of milk! Pitt and Aniston wed in 2000, and everyone thought they were an adorable couple — until he met wild lady Angelina Jolie on the set of their 2005 flick Mr. & Mrs. Smith, and Aniston was history.

The globe-trotting couple adopted three kids and had three biological children. For a while, their lives seemed heavenly.

Jolie said in 2008: "It is chaos, but we are managing it and having a wonderful time."

But then, oops, things went south and they’ve been at war ever since 2016 when she filed for divorce, accusing him of abusing the kids and leaving them frightened for their lives, which he denied. Son Pax Jolie-Pitt, 20, said his dad is "an awful human being" and a "world-class a------," and there’s never a week in which either Angelina or Brad isn’t accusing the other of something terrible.

Where to begin. This guy has a different beauty on his arm every week!

The Titanic star has tons of cash — $300million of it — but come on, he never stops wooing young women. And insiders said this tiger is never going to change his stripes.

The 49-year-old Killers of the Flower Moon heartthrob has been linked to dozens — and dozens — of models and A-list ladies — most of them young enough to be his daughter, but few of the relationships have lasted past the beauties’ 27th birthdays.

An insider said: "Everyone knows that ALL girls age out with Leonardo DiCaprio. It’s a definite dead end — but they seem to enjoy the ride."

Relationship experts said DiCaprio suffers from a Peter Pan complex that keeps him from growing up and committing to one woman, while pals said he has his partners sign nondisclosure agreements to keep a lid on his behind-closed-doors doings.

But spurned exes have revealed some shortcomings. Model Bridget Hall insisted "he was lousy in bed", and Tom Brady's ex, Gisele Bündchen complained DiCaprio was all about numbing himself with "smoking and drinking" before their relationship struck the inevitable iceberg.

Handsome Pirates of the Caribbean star Johnny Depp saw his reputation take a deep sea dive during a car-crash court case with ex-wife Amber Heard, who accused him of physical and psychological abuse. The not-so-coosome twosome were wed in 2015 and divorced by 2017, so those two years had to be CAR-AZY.

Although she was ultimately found liable for defamation, he was the one who ended up looking like an out-of-control party boy who your dad would warn you against.

Sources said the 61-year-old actor likes to drink and drug his way through life, while he stars in blockbuster movies and rocks out with his touring band, the Hollywood Vampires.

Actress Ellen Barkin — who reportedly had a fling with Depp while making the 1998 film Fear and Loathing in Las Vegas — said he "was always drinking and smoking a joint" and once allegedly threw a wine bottle at her.

But he’s got a lot of dough – $150million.

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