15 Actors Who Have Aged Horribly Compared To Their Female Exes

There is a lot of pressure to look great at all times for celebrities in the spotlight. There's even more pressure on them to appear young and ageless throughout their career. But as you're going to find out below, there are plenty of female celebrities whose former boyfriends or husbands are looking a little worn for wear in 2016. We bet that these ladies are happy to say they are no longer with them, and the gentlemen are probably smacking themselves silly for letting these gorgeous women slip away.

Sure, women have cosmetics, procedures, lasers and plastic surgery; but some of these Hollywood men have dabbled in that as well. Hey, it's Hollywood. Although a few of them definitely should have stayed away from the knife; more is not always better.

Macaulay Culkin is now the skeleton of a man with ghastly features, while his stunning ex, Mila Kunis, has been named one of the hottest women in the world. Former supermodel, Cindy Crawford, is married with kids and still looks like she could hop onto a runway any day; while her ex, Richard Gere, is looking more like an old man you'd have to help across the street than a heartthrob Hollywood actor, and those are just the tips of the iceberg. Check out this list below to see 15 actors who have aged horribly compared to their female exes.

15 Mickey Rourke & Carré Otis

Via patriotnation and twitter

Mickey Rourke & Carré Otis were involved in a turbulent marriage that eventually resulted in the two divorcing one another. It did not help that Mickey's proposal to Carré involved him threatening to kill himself with a hari-kari sword if she didn't say yes, probably not the best way to start off a marriage.

Former model Carré Otis, later revealed details of her troublesome relationship with Rourke in a memoir called Beauty Disrupted. In the book, she recalls how she was shot after Mickey had stashed a handgun in her bag without her knowledge. It seems Mickey's beauty has also been disrupted, as the once bad boy rising star of Hollywood is looking pretty rough around the edges these days. The cigarettes aren't helping that face look any better either.

Carré Otis has remained fairly under the radar since her divorce from Mickey Rourke, but one thing is for certain, she is definitely looking a lot better than her ex-husband these days. Mickey looks like he has had more work done that she has, and it only made things worse!

14 John Travolta & Kelly Preston

Via vh1 and picsofcelebrities

John Travolta and Kelly Preston broke headlines a few years ago after Travolta was allegedly caught having an affair with the maid.

The pair of big screen actors even worked together on a couple of films like Old Dogs, Battlefield Earth, and The Experts. No longer the tall, dark, and handsome star of Grease, John Travolta is a botoxed, pale ghost of the man he used to be. Maybe it was the fear of aging that made Travolta go so crazy with the cosmetic surgery over the past few years, but if anything, he is looking older than ever. Is that tattooed eyeliner he's got going on there?

Kelly Preston, on the other hand, is a mother to their three children; Ella Bleu, Benjamin, and Jett, and is still looking fabulous at the age of 53. While there were heavy talks of their separation, including a $240 million potential divorce this past October, the two have undergone heavy counseling and have actually been able to patch things up (at least as of now).

13 Matthew Perry & Lizzy Caplan

Via tvguide and celebmafia

Friends star, Matthew Perry, and Mean Girls actress, Lizzy Caplan, dated for six years but were hardly ever photographed together in public. The couple allegedly split because Perry was not ready to commit to marriage.

Well, he is probably hitting himself in the face now. Lizzy Caplan looks striking while he appears to have grown a second chin. Perry has not aged too gracefully, but it doesn't appear that he has had any work done. Lizzy Caplan starred on the hit series, Masters of Sex, while Perry has been given some roles on a few sitcoms, none of which have lasted. Lizzy Caplan made her red carpet debut back in the winter of 2016 with her new beau and opera performer, Tom Riley. Matthew Perry's current relationship status is unknown.

12 Ozzy Osbourne & Sharon Osbourne

via Mirror UK

The hierarchies of the OG reality TV family, 67-year-old heavy metal rocker Ozzy Osbourne and 63-year-old co-host of The Talk, Sharon, have broken up after more than 33 years of marriage.

The pair told media that they had mutually agreed that Ozzy would move out of the house on a temporary basis. Sharon Osborne also stated that their split had nothing to do with the state of Ozzy's sobriety. There have been rumors circling that Ozzy has a sex addiction and that may have played a role in the divorce.

Ozzy and Sharon Osbourne met back in the early 70's when Ozzy rose to fame with his band, Black Sabbath. Sharon eventually became the band's manager and the two struck up a romantic relationship. The Osbournes were married in 1982 and they have three children together. The family starred in the hit MTV reality series, The Osbournes, between 2002 and 2005. Clearly, the years of sex, drugs, and rock and roll have taken a toll on former rock star Ozzy Osbourne. Ozzy has also undergone plastic surgery, admitting to having had a nose job and a facelift to boost his confidence.

Sharon Osbourne is also not new to plastic surgery, as the rocker's wife has had many procedures including having her legs and arms lifted, and a tummy tuck following having a gastric band fitted. But nevertheless, Sharon looks lively and youthful at the age of 63 while her husband just looks like a little like a vampire with waxy skin.

11 Macaulay Culkin & Mila Kunis

Via dailydot and youtube

Mila Kunis is easily one of the most beautiful women in the entertainment business, she could have any man she wanted, so why on earth was that man Macaulay Culkin?

Mila Kunis and Macaulay Culkin were in a famously long-term relationship for around eight years before they broke things off. Macaulay Culkin was once one of Hollywood's biggest child stars, earning millions for his parts in films by the time he starred in Richie Rich in 1994. However, like many child stars, as Macaulay got older, his life took a downward turn. Culkin's parents began fighting for control over his fortune, which was estimated to be between about $11-28 million. A lot of that money was spent on lawyer fees eventually leading to Macaulay handing over financial control to his accountant.

Mila Kunis has had a remarkably successful career, starting off as one of the stars of the popular series That 70's Show, and successfully transferring over to big time movie roles in films like The Black Swan, Ted, and Moms. The actress is happily married to 70's co-star, Ashton Kutcher. The couple is expecting their second child together.

10 Johnny Depp & Winona Ryder

Via etonline and celebmafia

"Winona Forever" or maybe not. Johnny Depp and Winona Ryder had an infamous relationship together during the nineties. The couple were wrapped up with each other and their romantic connection and were engaged after five months. Johnny and Winona even starred in the classic film, Edward Scissorhands, together.

Depp was so infatuated with Winona, that he had her name tattooed on her arm inside of a heart. When they separated after four years, Depp had his tattoo inked over, so now it just reads: "Wino Forever."

Maybe too much booze is what did it for Depp, but he is looking weathered and aged these days. Depp is in the midst of an extremely public divorce including accusations of physical and emotional abuse made by his soon-to-be ex-wife, Amber Heard.

Winona Ryder has just starred in the new and popular Netflix series, Stranger Things, and the actress is a happy mother and wife. Winona is married to Scott Mackinlay Hahn, a silver fox, an American fashion designer and co-founder of ROGAN and Loomstate sustainable apparel brands. At the age of 43, Ryder looks more youthful and radiant than ever before.

9 Val Kilmer & Joanne Whalley

Via mirroruk and fanshare

Val Kilmer has been called one of the most difficult and ruthless men of Hollywood. His ex-wife, British actress, Joanne Whalley, has demonized Kilmer in the press. Whalley was forced to take the Batman star to court for unpaid child support. The pair were married from 1988 until they divorced in 1996, citing irreconcilable differences.

Kilmer started out as a well-liked actor and had breakout roles in films like Top Secret!, Real Genius and Top Gun. But Val Kilmer is not very well received in Hollywood these days and he has alienated pretty much every director he has ever worked with. His looks are also long gone and what remains is a frail, sickly looking man.

Kilmer is reportedly suffering from throat cancer, which he will not get treatment for because he claims that religion will heal him. Good luck with that, buddy. Meanwhile, Joanne Whalley has been busy at work this past year, getting involved in the TV mini-series, The White Princess due out in 2017 and a few other series last year including A.D. The Bible Continues and The Borgias. 

8 Bruce/Caitlyn Jenner & Kris Jenner


Bruce and Kris Jenner were married in April of 1991 and were married for 23 years before divorcing. One of the main reasons for the divorce was due to the fact that Kris' husband, Bruce, decided to transition his gender and is now known as a 66-year-old woman named Caitlyn Jenner.

They divided up their assets and Kris will keep the family home, with neither receiving spousal support, but it is claimed that Kris will need to pay $2.5million to Bruce to even things out.

It was pretty obvious that Bruce was not aging too gracefully even before he made his transformation. Victim of one too many botched facelifts, Bruce's face looks like it has been nipped and tucked to its full extent.

Kris Jenner has had her fair share of work done as well, but she looks just as confident and glamorous as ever. Maybe now that her ex-husband is a woman, she could share her plastic surgeon with him/her?

7 Steven Seagal & Kelly Le Brock

via:fanshare and picsofcelebrities

Steven Seagal and Kelly Le Brock had a volatile relationship and an even more tumultuous divorce. Three women have spoken out after the marriage alleging that they were sexually and physically abused by the Hollywood actor.

Kelly Le Brock basically went into hiding and became a social hermit following her divorce. She has custody of the couple's three children and lives in Santa Barbara, California. After the divorce, she moved her children out of Los Angeles so that they would be able to grow up in a more normal, stable environment. Before her marriage to Seagal, Le Brock was a successful model and actress herself. LeBrock rose to fame in the 80s in iconic films like The Woman In Red and Weird Science, but has stayed out of the spotlight for two decades.

One of LeBrock’s more high profile modeling jobs was for Pantene hair care products. In the commercial, when LeBrock famously said to audiences “Don’t hate me because I’m beautiful”.

6 Russell Crowe & Danielle Spencer

Via abcnews and popsugar

Russell Crowe and Danielle Spencer separated after nine years of marriage. Both Russell and Danielle are musicians and actors. The couple have been in an on-again, off-again relationship since 1989, with the pair marrying in 2003, before welcoming their two sons Tennyson (9) and Charles (12).

The two amicably co-parent their children together. Crowe allegedly cheated on Spencer during their marriage. Though the two have not legally filed for divorce, they have been separated for more than a decade. The Gladiator star seems to be holding out on hope that the two will eventually reconcile stating, "We haven't done the deal yet. I'm a very persistent person, you never know, I didn't get married to get divorced."

The Oscar winner continues to try and convince Danielle Spencer to rekindle their relationship in the future. Although, she is looking a hell of a lot better than he is these days, so who knows if Spencer will even want him back.

5 Sylvester Stallone & Brigitte Nielsen

Via youtube and celebritywc

Sylvester Stallone and Brigitte Nielsen were married for less than two years. Stallone sought out a divorce from Nielsen when he was 41 and Nielsen was 24. Stallone cited "irreconcilable differences." The only other option for the dissolution of marriage in California is "incurable insanity," so at least he didn't go with that one.

Nielsen was rumored to be romantically involved with Tony Scott, her director in Beverly Hills Cop II. It was even rumored at one point that Nielsen might be a lesbian and that she allegedly had an affair with her female secretary, Kelly Sahnger.

When they met in 1985, Stallone was at his peak, starring in big time hits like Rocky and Rambo movies. Nielsen was a model and had already made Red Sonja, but her career only really started to pick up after she became involved with Stallone. She landed roles in Rocky IV, Cobra and Beverly Hills Cop II, jobs she almost certainly would not have gotten if it were not for Stallone. Nielsen is often accused of marrying Stallone solely for the purpose of enhancing her career, but she has strongly denied this claim.

4 Al Pacino & Beverly D'Angelo

Via rolex and cambio

Al Pacino and Beverly D'Angelo share a child together from their relationship in 1996-2003. So while their relationship may have only lasted seven years, they are connected to each other for life.

Al Pacino is one of the biggest names in Hollywood. He is well-known for portraying this tough guy, intense persona, for example, his role in The Godfather. But long ago were the days when Al Pacino was a desirable bad boy. These days, Pacino is looking more haggard than ever and his face is gaunt and pale.

Beverly D'Angelo is also a pretty successful actress on her own, best known for her roles in National Lampoon's Christmas Vacation, Harold & Kumar Escape From Guantanamo Bay, Cougar Town and Entourage. D'Angelo is definitely looking a lot better than her deadbeat ex, Pacino. At the age of 64, the actress still looks strikingly beautiful. We can't say the same for Al. 

3 Jack Nicholson & Cynthia Basinet

Via youtube and allaboutjazz

Jack Nicholson and Cynthia Basinet were linked to one another for two years in the late nineties from 1997-1999. Jack Nicholson has racked up quite the impressive list of ladies he has dated in the past, especially since he is not the most beautiful man to look at. The years have done nothing but stretch his belly and widen his wrinkles.

Nicholson was involved in a few notorious relationships over the past few decades including supermodel Kate Moss, Rebecca Broussard, Janice Dickinson and Margaret Trudeau.

Cynthia Basinet is a Nobel Peace Prize-nominated critically acclaimed self-released singer-actress activist. Her jazz version of "Santa Baby" was originally made and dedicated to then-boyfriend, Jack Nicholson. Have fun thinking about that next time Christmas rolls around. In 1999, the entrepreneurial-minded actress became one of the first few artists to gain her exposure through the Internet. Makes it easy to also understand why she is long considered to have one of the most sultry and seductive voices in the history of music. Nicholson sure did let a good one slip away, but it seems this playboy will never settle down for good.

2 Richard Gere & Cindy Crawford

Via USAToday and TODAY

Actor Richard Gere and supermodel Cindy Crawford, were married for four years until their split in 1995. Part of their incompatibility may have been due to the fact that there was a significant age gap between the couple, Gere was 42 and Crawford was just 26.

The exes are now practically strangers. Cindy Crawford went on to marry for the second time to entertainment businessman and former model, Rande Gerber.  The couple have  two equally gorgeous, angel-faced children, Kaia Jordan Gerber and Presley Walker Gerber. Kaia has already taken a step into her mother's shoes- starting her modeling career off at just 14-years-old. Her mother, Cindy, still looks practically ageless after more than twenty years since being married to Gere. Crawford could easily step on to any runway and still work it like she always has.

Age has definitely taken a toll on Richard Gere, who was once had women everywhere drooling after him in movies.

Fun Fact: Did you known that Richard Gere's middle name is Tiffany? Well, you do now. Richard Tiffany Gere went on to marry once again in 2002 to Carey Lowell. But after 11 years of marriage, the couple got divorced.

1 Leonardo DiCaprio & Gisele Bündchen

Via elitedaily and ztnent

Leonardo DiCaprio and Gisele Bündchen were once one of the best-looking and most glamorous celebrity couples. Unfortunately for DiCaprio, Bündchen is now living happily ever after with her professional football quarterback Tom Brady, while he is still dating numerous young models who are pretty much just using him for his money these days. Have you seen the guy?

DiCaprio and Bündchen shared a whirlwind 5-year romantic relationship with one another. He was one of the biggest actors and she was the supermodel of the century and together they looked absolutely perfect, but they broke up in 2002.

Sources close to Gisele claimed that she simply grew tired of him. She had moved to L.A. to be with him, but the paparazzi followed them so heavily that they rarely got to go out in public together. Giselle eventually moved back to the fashion capital, N.Y.C.

Gisele is settled down living with her husband and their children, Vivian Lake Brady and Benjamin Brady in the glamorous L.A. Brentwood neighborhood. While Leo is seemingly doing what he has always done, finding the next blonde model to sport on his arm for the time being.

At 36-years-old, Gisele just retired from the professional modeling world last year, although, with those looks, she could probably have continued for at least another decade. The former supermodel and her family enjoy living a healthy and environmentally friendly lifestyle. Leo is now 41-years-old, but with all of the boozing, cigarettes and God only knows what else, his face is looking a decade older than that.


Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Entertainment

15 Actors Who Have Aged Horribly Compared To Their Female Exes