If you haven’t already heard, Richard Gere, the actor most people my age will only be able to identify as the guy from Pretty Woman, recently married Alejandra Silva. Ordinarily there would be absolutely nothing spectacular about that kind of headline, but the catch is that, at 35, Silva is just about exactly half the age of the 68 year old actor. They got hitched about a week ago, and, though we’re happy for Gere and wish him all the best, we can’t help but gawk at the odd couple.
Now, there are plenty of celebrities who’ve managed to nab someone much younger than themselves — it’s almost a Hollywood tradition. Yet, while those who pride themselves on their open mindedness aren’t likely to find anything objectionable about these relationships, the rest of us can’t help but feel that there’s something wrong about the pairing. Sure, if they want to get married, that’s up to them, but in the back of our minds we all feel that this marital bond will only be a lifetime commitment for one of the partners. I don’t mean to be grim, but, when a 35 year old walks down the aisle with a man double her age, well, that thought has to cross everyone’s minds.
It might be one of the more extreme examples of celebs marrying outside of their age range that we’ve seen in recent years, but it doesn’t quite crack some of the more bizarre weddings we’ve seen over the years.
20 Richard Gere Found His Pretty Woman
So, as I’ve mentioned, Richard Gere just tied the knot with Spanish publicist Alejandra Silva. A strange match, to be sure, but that’s not to say that is a pairing absence of merit. The two have known each other since they were young… well, since she was young, I’m assuming Gere would have been somewhere around the age of 50 at the time. They also seem to have bonded over their roles as community activists, which is a great way to get to know one another.
I have to say, however, that, from the perspective of someone who was born five years after the release of Pretty Woman, he seems extraordinarily old. I don’t mean to insult the man, but he had a sort of just-past-his-prime, silver fox-esque heir to him in that role… but that was in 1990, nearly thirty years ago. To be fair, Gere’s new wife is about fifteen years older than Julia Roberts was when she portrayed the seductive Vivian Ward, but I guess his affinity for younger women would never be satiated. He may have been a heartthrob in his time, but today he’s got something of a quiet, elderly vibe to him. Pretty Woman may have been the Fifty Shades of Gray of 1990, but, as Gere well knows, time has marched on.
19 Michael Douglas Has A Wife Who Stands By Him
Tons of these celebrity odd couples fizzle out after more than a few years, but, eighteen years after their marriage in 2000, thespians Michael Douglas and Catherine Zeta-Jones are still together, and they claim that the love is still there, too. This one isn’t quite as bizarre as the aforementioned mile-wide generational gap between Richard Gere and his wife, but it’s noteworthy nevertheless.
Both Douglas and Zeta-Jones have had illustrious careers in Hollywood. Douglas has been in more movies than you could probably count, been nominated and received numerous awards, and even directed his own films. His wife is equally notable, though their true common trait is that they’ve both won Oscars—his for the movie Wall Street, and hers for Chicago in which she co-starred with none other than Richard Gere. Small world, I suppose.
I certainly wish all the best to this happy couple, though I do feel that, if some of your best work was produced in the 80’s, you should probably start feeling old. Zeta-Jones doesn’t quite have that problem, though, as she seems to have been more of a big name during the turn of the century. That’s when she married her spouse, though, and I’m guessing it was just as weird back then as it is now.
18 Woody Allen Started Controversy
You knew this one was going to be on the list. I hardly know what Allen is actually famous for. He’s an actor, director, and comedian, but, outside of his infamous marriage, I’m not sure why anyone really knows his name. That may offend some of his avid fans, but, if I am too young to tap into his impact on the public consciousness, then I would be willing to bet that his spouse doesn’t know why he’s popular, either.
That’s not nearly as hyperbolic as you might think: though Allen was married to actress Mia Farrow at the time, his history with Soon-Yi Previn, his current spouse, goes back as far as 1992 when she was 21 years old. Allen would have been 56 years of age at the time, which is more than a little gross. They later married in 1997 when she was 27 and he was 62. The mathematically minded will already have discerned that that’s a gap of about 35 years.
Again, they’ve been together for a while, and I don’t want to perpetuate the idea that restrictions should be imposed on relationships, but this is just weird. More than 20 years on, Pevin is, at 47, still much younger than Woody was when they first met.
17 Ronnie Wood Is Still Having Kids
Tons of people question how Rolling Stones icon Mick Jagger could have survived through his years of partying and gone on to continue his career into his golden years. Plenty of artists are like that: Aerosmith’s Steven Tyler, Black Sabbath’s Ozzy Osbourne, and Neil Young have all gone on to outlive almost everyone’s expectations, so the fact that Ronnie Wood is still kicking it with the Stones isn’t all that surprising or exceptional.
What is extraordinary, though, is his marriage to Sally Humphreys, his wife of five years. In their heyday, plenty of young girls would have loved to get to know any of the famous British musicians, but, in 2012, Humphreys took that notion to the extreme when she actually tied the knot with the famous Stones rhythm guitarist. He’s 70 now, and she’s about 40, which makes for quite the generational divide. What’s more, however, is that she actually gave birth to twins sometime in 2016, which as a borderline absurd notion. Not only did she have children pretty late in life, but he absolutely had kids much later than he should have. Just imagine: when his twins are 20, he’ll be about 90 years old — he’s literally 70 years older than his kids!
16 Nelson Mandela Found Someone Like Him
Most people know Nelson Mandela as the revolutionary South African leader and human rights activist who helped bring an end to the racial inequalities of apartheid. Jailed for 27 years, his eventual release and subsequent ascendancy to the highest South African political office is a story which will be told for generations to come, but that’s only half of his story. Few know that he actually had something of a difficult and controversial romantic life — he’s on this list, after all.
He was married to Winnie Mandela for nearly 40 years, and for the entirety of his infamous prison sentence. Married in 1958, Winnie is credited with helping to keep his cause alive during his near three-decades behind bars. When he got out in 1990, he accused her of being a bad wife, and, though his profile was only heightened by his release, things never cleared up with his wife, whom he divorced six years later.
15 Larry King Is Making It Work
If you know anything about Larry King, then you probably know that his marriages quite often tend to fizzle out after a short amount of time. King was first married all the way back in 1953 to his high-school sweetheart, though his parents evidently forced them to break it off a year later because they didn’t approve. He was remarried and had his first child to a different woman in 1961. He’d be remarried three times in that same decade, having his second child with his fourth wife in 1969. Three marriages after that, the famous TV host apparently landed on his true one-and-only when he married Shawn Southwick in 1997. They have had two sons together who are 17 and 19, which creates an age gap between siblings longer than some of the age gaps between spouses I’ve mentioned already.
His marriage to Southwick has lasted for over 20 years now, though, so they’ve clearly been able to make it work.
She is much, much younger than him, however. At 58, King quite literally has children the same age as his current wife, which is very, very uncomfortable to think about. Rumors have been circulating that this marriage is collapsing, though the two are still together for the moment.
14 Steve Martin Is The Biggest Sweetheart On The Silver Screen
Who would you think is the older actor — Bill Murray or Steve Martin? I would have without a doubt said Bill Murray, but Martin is actually five years Murray’s senior. I suppose he’s been around for a while, and most of his notable works were released in the late '70s or early '80s. Take The Jerk, for instance, my favorite film in his body of material; it came out in 1979, which means that it’ll be turning 40 sometime next year. It’s ridiculous to think that it’s such an old movie, but it’s still a great example of comedic cinema.
Martin doesn’t have nearly the marital drama of Larry King, or most of the other celebrities on this list, as a matter of fact. He’s been married twice, though the first coupling dissolved in 1994 and didn’t even last ten years. Last year, however, he celebrated his tenth anniversary with his current wife, who is nearly too young to remember when The Jerk came out.
Anne Springfield was 35 when she married Martin in 2007, and he was a much older 61, an age gap of nearly 30 years. So, she actually was old enough to see the release of Steve’s hit film, but I doubt she was old enough to actually go see it in theaters.
13 William Shatner Will Go Down In History
William Shatner probably takes the cake when it comes to celebrities who are much older than you would actually think. Larry King is 84 years old, though I would guess many people assume he might be older than that. Shatner, however, is three years his senior, but doesn’t even come close to looking like it. Quite honestly, I would have guessed Shatner to be at least 15 years younger than he actually is.
That doesn’t really excuse the Star Trek phenom from marrying young, though he did anyway. Shatner married Elizabeth Anderson Martin in 2001 when he was 70 and she was 40. They’ve been married for a while, but the age gap must be extremely noticeable between the two. He must have already been a TV star when she was still in diapers, which is just such an odd thing to think about. I understand that this is kind of a commonplace thing in Hollywood, but I just couldn’t imagine marrying someone who could easily be the same age as one of my parents.
Wouldn’t that feel just a bit hypocritical: put your parents in a nursing home and marry someone who is their same age. Shatner’s remarkably sharp for a man of his age, but universal entropy shall take its toll on us all, eventually.
12 Clint Eastwood Can Do It All
An older crowd will recognize Clint Eastwood as the prolific, intense star of many Western action flicks in the '70s and then again, as the infamously gruesome Dirty Harry, the eponymous character of a series of films of the same decade. Younger audiences will remember him for his stellar performance in 2008’s drama Gran Torino, and for his role as a director in the fabulously orchestrated Lone Survivor. He’s got a stellar body of work under his belt, which means that few will remember the actor for his marriage to a woman literally less than half his age. In 1996, Eastwood married Dina Ruiz. He was 66 at the time, and she was a mere 31 year old — I wasn’t embellishing, she was literally less than half of his age.
Eastwood actually has children that are around his wife’s age, which must make for one extraordinarily interesting family reunions.
He actually spends a ton of time now directing movies, so he might not have the time for stuff like that. This doesn’t really affect my opinion of the guy — to many people, he’ll always be a star. He changed the American cinematic landscape for the better, and he continues to do so in the modern era. Though marrying someone easily young enough to be your child is beyond weird, I think most of us will be willing to overlook that aspect of his life.
11 Frank Sinatra Was A Ladies' Man
What do Woody Allen and Frank Sinatra have in common? Well, they were both married to Mia Farrow at one point. I realize that Farrow is getting on in years, but it just seems too bizarre to be true. Though he only passed away in 1998, Frank Sinatra, the most recognizable of the Rat Pack musicians, feels very much like a relic of a very bygone era. Perhaps that’s simply because grandparents the world over love his music, or maybe it’s because most of his famous material came out a long, long time ago. Either way, I honestly thought that the image of him and a young Mia Farrow must be photoshopped, it felt like a strange meeting between the old and the new. Remember: his song Fly Me to the Moon came out well before anyone actually did fly to the moon.
He was exactly 30 years older than his ex-wife, who was a fashion model at the time. It’s funny to think that, at one time, Farrow may have been content to be the trophy wife of a world-renown singer, as she’s become so much more than that over her extensive career. It’s just such an odd circumstance, and I wish I could ask her what being married to him was like.
10 Paul McCartney Founds Someone To Hold His Hand
Here’s a PSA: If you search for Paul McCartney on Google, you’ll come up with one of the most unflattering images I’ve ever seen of the man. On the first page of the search results you’ll see a short biography about the musician, and the image they chose to include is so completely abused that it’s almost hilarious: he’s cross eyed, drinking out of a black mug that he’s holding from the bottom despite it obviously having a handle. You may say that doesn’t have anything to do with the topic at hand, but you really need to see this picture.
McCartney’s marriage is one of the less ridiculous covered here: his wife, Nancy Shevell, is 58, whereas he will be celebrating his 76th birthday on the 18th of June. That’s only an 18-year age difference, and, while that may sound like a lot out of context, there are so many more outlandish celebrity marriages. Of course, marriage was what ultimately led to the demise of certain uber-famous quartet for which McCartney is famous. It wasn’t his marriage, rather bandmate John Lennon and Yoko Ono were the main contributors to the demise of the legendary Beatles group, but you would think he wouldn’t have been quick to marry after that.
9 Kelsey Grammer Was Part Of A Scandal
Kelsey Grammer has very much fallen from the public consciousness. Even those who are old enough to remember when Cheers was in its heyday will probably only have that information tucked away in the corners of their brains. “Kelsey Grammer,” most people 35 and up will say. “I know that name. Wasn’t he on Frasier?”
Yes, in fact, he was on Frasier, but I’m young enough to not really even know what that show was about. He was also on The Kelsey Grammer Show, which I can only assume to have been some kind of late night talk show in the vain of such eponymously titled 10 p.m. dynamos as Conan or Jimmy Fallon.
Grammer is apparently well-known enough to get away with marrying someone decades younger than himself. His wife, Kayte Walsh, is a full 25 years younger than her husband, a fact that apparently didn’t disturb either of them. Perhaps she was a really dedicated Cheers fan, or maybe his presence on the show didn’t have any effect on the marriage. Either way, it’s more than a little weird. They were only married in 2011 when the actor was 56 years of age. Walsh would have been 31 at the time, though, so that’s a bit of a gap.
8 Rupert Murdoch Is Mr. Media
Rupert Murdoch is one of the few celebrities on this list to not be the star of some show or the face of some brand. In reality, he isn’t a celebrity at all; he’s actually a powerful media mogul who has been responsible for the rise and fall of many careers, shows, and networks over the years. The unseen marionettist behind the tidal flow of television programming, Murdoch is actually somewhat known for marrying women much younger than him.
The 86-year-old, Australian-born media tycoon has had four separate marriages to date, one of which was to a woman known as Wendi Deng, and Murdoch was 68 when he married her in 1999. The only problem with that was that she was a mere 30 years old at the time, which is an age difference of more years than Deng had lived through at that point. He later divorced her in 2013 and married former model Jerry Hall three years later. She’s 59, but she is also no stranger to relationships with older men — she has four children with Rolling Stones frontman Mick Jagger! Say what you will about her romantic habits, but she must really know how to schmooze with the rich and powerful.
7 Sylvester Stallone Was The Biggest Name In Hollywood
I grew up near Philly, and, like all native Philadelphians, Rocky Balboa played a major part in my life. Ever the underdog, I’m not sure if Sylvester Stallone has ever really fully grasped the reputation he’s garnered in the city since Rocky came out all those years ago. He’s only grown in popularity since the town’s tremendous Super Bowl victory in February, and, if you walk down any street on the South side of the city on the day of a Phillies or Eagles game, and you’ll probably hear someone playing the film’s instantly-recognizable theme song.
That said, the man isn’t immune to error, and, though his marriage seems to have been successful, fans will still point out how odd it is that he married someone 22 years younger than himself. The actor married Jennifer Flavin in 1997 when he was 51 and she was a mere 29 years old. The pair have three daughters, and, as great as that is, one need only see a photo of the couple to realize what a strange match it is. I’m not sure how they met, but I would be willing to bet that their marriage had something to do with Stallone’s status as an actor.
6 Dick Van Dyke Is Historical
This probably won’t shock anyone, but, outside of his annual installment of New Year’s Rockin’ Eve, I’m not really sure… wait, no , that’s Dick Clark I’m thinking of. Who is Dick Van Dyke, again?
I’m only partially kidding. Dick Van Dyke was an actor and radio host who grew in popularity thanks to his roles in smash hit films like Mary Poppins and Chitty Chitty Bang Bang. He would go on to portray a few minor characters in films like Night at the Museum and Curious George, but I think most of his reputation stems from the work he did much earlier in the 20th century.
Again, he is very much a faded star who seems to have dropped from the public consciousness, and he’s actually so old that his first marriage, which took place in 1948, was broadcast on a radio show which focused on the weddings of young couples. Unfortunately, an affair between Van Dyke and Michelle Triola would cause the happy couple to separate in 1984, though Van Dyke and Triola remained an item until her passing in 2009. The radio broadcaster and TV host would go on to marry Arlene Silver in 2012. He was 86 at the time, and she was 44, so that’s yet another wife who is nearly half the age of her husband.
5 Billy Joel Found His Soulmate
I don’t mean to insinuate that they were in any way immoral, but the age gap here is so noticeable that it’s downright alarming. The famous singer-songwriter Billy Joel is well known for a slew of hits in the 70s and 80s, but, as time went on, he became less and less relevant. Today it seems that those who continue to follow him closely were fans since the beginning, and he isn’t exactly the sort to attract a new, younger generation of listeners.
Well, that’s not exactly true, as he certainly managed to draw the attention of one young fan in 2004 when he married 23-year-old Katie Lee. Joel was 55 at the time, and likely the same age as his bride’s parents, which is a profoundly disgusting thought. The couple didn’t last, however, as they formally separated in 2010. He had actually been married twice before, os it isn't exactly surprising that the singer couldn’t make this unlikely third marriage work out. I don’t mean to perpetuate the idea that he’s somehow unlovable, I just mean to imply that age gaps as wide as that can really damage most romantic encounters.
4 Patrick Stewart Found His Mrs. X
Esteemed Star Trek icon Patrick Stewart is a legend among sci-fi fanatics, and his legacy will likely never be forgotten amongst that particular fanbase, no matter how many spin-offs they make. Outside of the world of science fiction he’s garnered something of a following as Professor X from the X-Men series of films. Plus, he’s also a pretty well-known meme, which would be a huge resume booster. Even if you aren’t necessarily a fan of Star Trek, I would be willing to be that you have still heard the British actor’s name at some point in your life.
That said, he became a bit of a controversial figure for a brief period when he married Sunny Ozell in 2013. There’s an enormous age gap between the two lovers — one that’s two years short of being four decades long. He might portray some eccentric figures on television, but a move like this doesn’t seem befitting of the relatively mild-mannered actor.
The major age difference between the two doesn’t seem to have hampered anything, however, as the two are still together. Stewart is currently 77 years of age, and he hasn’t had a single strand of hair grow on his head for the past 40 years. Alright, that might be a bit of an embellishment, but it’s probably close to the truth.
3 Hugh Hefner Loved Blondes
Who else could close out a list like this other than the late Hugh Hefner? The man was pretty much born to be on this list. The founder of an infamous yet influential magazine the name of which I trust everyone to already know, Hefner’s publication essentially revolutionized the world of adult-centric entertainment. A legend unto himself, the mighty Hef was famous for having spent his days in a lavish mansion surrounded by scantily-clad models.
To the surprise of absolutely no one, Hefner had something of a sordid married life. Married thrice, his first divorce occurred a full 27 years before his third wife would even be born, which is nothing short of total insanity. As a matter of fact, Crystal Harris, model and close confidant of Hefner, was only 26 at the time of her marriage to the adult-magazine mogul. Hefner was a prime candidate for nursing home residency at the time, however, as he was 86 — that’s an age gap of 60 years! That’s more than double the age gaps between some of the other celebrity couples mentioned on this list, but what more would you expect from a man as infamous for this kind of thing as Hugh Hefner.
2 Alec Baldwin Defends His Woman
The most recognizable of a familial slew of thespians, Alec Baldwin hardly needs an introduction. He’s been in movies of seemingly every genre, and his skills as an actor have seen him in numerous television roles, and even several spots as the host of late night TV staple Saturday Night Live. His wife, however, is something of an unknown. From what I can tell, her largest claim to fame is her husband, though she actually owns a few yoga studios in New York City.
Baldwin might be aging, but I would hesitate to label him as an older actor. He’s been around for quite a while, sure, but he doesn’t exactly look like he should be making plans to move into a nursing home soon. His wife is pretty young though. Born in 1985, she’s a full 26 years younger than her spouse. Ordinarily I would suggest that an age gap of anything more than eight to ten years is a bit strange in couples, but, for whatever reason, I don’t get that uncomfortable feeling when I see these two. Baldwin is actually 60, though, and his wife is a spritely young 34. When you put it that way, it does sound a bit creepy. Alec Baldwin actually made his film debut in a 1987 film called Forever Lulu, which means that he’s been acting since his wife was literally in diapers.
1 Harrison Ford Loves His Wife
I actually didn’t know this, but Harrison Ford is getting really, really old. I mean no disrespect to the guy — it’s something that’ll happen to all of us — but I honestly didn’t realize that he’s as old as he is. When I saw him in 2015’s Star Wars: The Force Awakens, I thought he might have been in his early 60s. Perhaps a bit haggard for that age, but, in reality, the Star Wars legend recently celebrated his 75th birthday. It’s weird to see someone like that age, as I always picture him as the young and in-shape Indiana Jones of the 1980’s, not a white-haired old man with a penchant for crashing planes.
That aside, he’s also pretty well known for saying his vows with someone drastically younger than himself. He began dating Calista Flockhart in 2002 at the age of 60. She was only 38 at the time, which meant that there was a 22 year rift between the two. They married in 2010 and appear to still be going strong as a couple. In fact, People once described their marriage as unshakable, which is great news. Han Solo may have ditched Princess Leia, but, in real life, Ford knows how to remain faithful.
References: imdb.com, wikipedia.com, people.com, eonline.com, people.com