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The Most Rarely Seen Old Pictures Of Celebrities

By

Ami Ciccone

, updated on

July 8, 2018

There is no doubt that history has a lot to teach us. But sometimes, it's good to take a trip down memory lane and revisit some of the best times when our favorite celebrities used to do things which they no longer do, either because they have completely changed as people or because, unfortunately, they are no longer alive. Here we catch a glimpse of some of our favorite stars before they started making money and earning millions with their immense fame and those celebrities who failed to cope after having made a fortune.

Princess Diana & Prince Harry, 1987

There is a reason why people used to call Diana the People's Princess. It is because of her royally unconventional down-to-earth personality. Princess Diana undertook her responsibilities as a royal. But after giving birth to Prince William and Prince Harry, she embraced motherhood just as well as her other roles. In this picture, we see her giving a piggy-back ride to Prince Harry, which gives an unfamiliar sight of a royal but a scene completely in sync with Diana's earthly character. 

Nicole Kidman, 2001

If you are looking for divorce advice, then Nicole Kidman is the person you should be contacting, and here's why. Just look at this picture of her allegedly having just exited the attorney's office after finalizing the divorce papers to legally end her marriage to Tom Cruise. The celebrity couple remained married for around eleven years. And although Nicole has remarried to Keith Urban in 2006, we can't help but reminisce this iconic picture of her every now and then.

Michael Jackson & Paul Mccartney, 1982

Here is a picture of two of the most iconic musicians of the 20th and the 21st centuries, Paul McCartney and Michael Jackson, casually washing the dishes back in the '80s. Of course, this was before both of them entered a feud about rights to the music produced by The Beatles. Although the details of the said feud vary by who is telling the story, what remains as a fact is that Paul McCartney did not have a favorable opinion of Michael after that incident, of course, until Jackson passed away in 2009 of a prescription drug overdose.

Princess Diana & John Travolta, 1985

Princess Diana's tragic accident in Paris, France left the world heartbroken. Now, we only have pictures of her to remember her by. Many of her pictures while out in public remind us of the humility she possessed. But it's no secret that Diana was also a style icon. Just look at this picture of her wearing a black evening gown with a beautiful necklace dancing with one of the most famous actors in Hollywood, John Travolta.

Meryl Streep, 1981

If you, like many others, also believe that this picture of Meryl Streep was taken on her way back from an audition for the movie King Kong, on which she was rejected for being too ugly to perform the role, then you too fell for an internet hoax that made for a sensational story. This was shared numerous times after first making an appearance on her Facebook fan page (which has since been deleted by Facebook). The picture was actually shot by the professional photographer Ted Thai.

Barack Obama, 1990

Most of us started getting to know Barack Obama in the 2000s when he started making great strides in politics, eventually winning the presidency back in the 2008 US elections. But Obama was not an ordinary figure from the very start. This fact was made evident by this 1990 cover of the Vanity Fair magazine which featured the then-budding lawyer Obama after he had won the presidency of the coveted Harvard Law Review at just 28 years old.

Justin Timberlake & Ryan Gosling, 1994

You would not believe that now-heartthrobs singer Justin Timberlake and actor Ryan Gosling were once part of The Mickey Mouse Club when they were both around 13 years old. This picture of them is from around that time when they had only started making money as artists. Unfortunately, it does not seem like they are the best of friends now. Although, they do seem to have remained on amicable terms. Both were photographed exchanging greetings at the 89th Academy Awards.

Sophia Loren & Jayne Mansfield, 1957

One of the most iconic Hollywood rivalries in history has to be between actresses Jayne Mansfield and Sophia Loren. This picture of them both sitting at a table, in which Loren is giving Mansfield a side-eye, still lives on as the perfect depiction of their professional rivalry. The picture was taken at the welcome party thrown by Paramount in honor of Loren, who had just signed a contract with the company. Mansfield came wearing a dress that was perhaps too revealing, taking all the attention away from Loren.

Prince Harry & The Spice Girls, 1997

No matter how many pictures you have seen of Prince Harry in the recent past, especially due to the fact that he married Meghan Markle this year in a spectacular royal wedding, this is one picture which you must not avoid as it reminds us of the beautiful '90s when the Spice Girls ruled the music scene. It also serves as a great comparison point to notice how far Prince Harry has come, emerging as the handsome and responsible young man he is today.

Amy Winehouse, Late '90s

Amy Winehouse became a part of the 27 club (an unofficial club of those famous artists who died at the age of 27) when she died from accidental alcohol poisoning in 2011. Her brother Alex revealed that Amy had been suffering from bulimia, which left her weak enough to not be able to deal appropriately with the amount of intoxicant she was consuming. This picture of an innocent-looking Amy in Paris during the late '90s shows a very mellow side of her.

Brad Pitt & Jennifer Aniston, 1998

These pictures show Friends star Jennifer Aniston and actor Brad Pitt attending a concert in LA, around the time when they had only begun dating back in 1998. The couple got married a couple of years later. However, their relationship ended in 2005 due to disputed reasons such as possible infidelity (many think it happened because Brad fell in love with Angelina Jolie). Now that Brad and Jen are both unmarried once again, maybe we'll get to see them both together eventually like many fans have wanted ever since their first split-up.

Marilyn Monroe, 1960

This picture from the set of the last film which Marilyn Monroe completed perfectly sums up the kind of power she exuded as an actress, exercising complete control over the photography session at the set of her 1961 film The Misfits. Monroe is one of the early deaths the world had difficulty reconciling due to its suddenness, as the actress died of an overdose, possibly intentional, at the tender age of 36.  

Prince Charles, Spice Girls & Jennifer Aniston, 1997

Now here is a picture combination we thought we'd never get to see at least during our lifetime, with Prince Charles, Jennifer Aniston, and Ginger Spice from the Spice Girls, all in one frame. We wonder what was so funny that both Ginger and Prince Charles lost composure in such a public setting, although we must commend Jen for maintaining it with a humble smile. Members of the Spice Girls have frequented events hosted by the royal family, so it's safe to say that they share a friendly bond.

Amy Winehouse & Blake Fielder, 2000s

It is no secret that Amy Winehouse and her husband Blake Fielder, whom she divorced in 2009, had a rocky relationship. Apparently, the story behind this picture according to Tumblr users is that both of them entered into an argument which prompted Blake to sit down on the pavement. Amy then joined him by sitting in front of him, and both of them seem to have sorted out the issue, whatever it was. Amy died in 2011 due to alcohol poisoning. And although Blake is still alive, he too is known for his use of addictive substances.

Cameron Diaz, 1989

Youth is truly a gift, and nobody can attest to that fact better than Cameron Diaz. Here you can see Diaz when she was only 17 years old. Although the actress has a lot more money and fame now than she did at that age, we bet she would give anything to look like her old self. The Charlie's Angels star got married to rocker Benji Madden in 2015 and is now expecting a child.

Penelope Cruz, 1993

Penelope Cruz started making money as a teenager, with her first role in a 1989 music video. By the time this picture was taken in 1993, Cruz had already established herself as a recognized face in the film industry. Her Oscar win in 2009 for an amazing performance in the film Vicky Christina Barcelona is proof of her unique beauty and talent. She married Spanish actor Javier Bardem in 2010 and the pair shares two children together.

Amy Winehouse, 2011

The picture accurately sums up the sentiment Amy must've felt after delivering a shocking (in a bad way) performance at her last concert in Serbia. According to audience testaments after the show posted on Youtube and other social networking websites, the singer looked drunk and disoriented as she slurred her way through some of her biggest hits. Amy herself acknowledged her terrible performance and refused payment for the same from the show organizers. Sadly, she died the same year due to her addiction.

Winona Ryder & Matt Damon, 1990s

Winona Ryder became one of the leading stars in Hollywood during the '90s, and so did Matt Damon. Both of them delivered some of their career-best performances during that era. And as their earnings inflated, it was only fitting that they also dated each other and attempted to become a Hollywood power couple. Clearly, that did not transpire, and their perplexed expressions in this photo show how confused they were themselves about this whole thing. Or maybe they just don't like being photographed while eating. Who does?

Jennifer Aniston & Brad Pitt, 1999

The cast of Friends became friends in real life as well. This did not come as much of a shock to anyone considering that they worked together for around 10 years filming the ten seasons of the hit TV sitcom. Here we see Brad Pitt and Jennifer Aniston attend the wedding ceremony of her Friends co-star Courtney Cox with David Arquette back in 1999. Although the Cox-Arquette marriage ended in a divorce (and so did the Aniston-Pitt one), this picture has forever preserved both the relationships in Hollywood history.

Salma Hayek & Johnny Depp, 1995

We're not sure which event they were attending but back in 1995, we got a glimpse of how two leading figures in Hollywood, Salma Hayek and Johnny Depp, looked amazing together on the red carpet. That same year, Salma was featured in four films while Johnny was featured in three. Both of them were quite obviously very busy making money at that point in time, which earned them a spot among the richest stars in the industry.

Charlize Theron & Leonardo DiCaprio, 1997

When Charlize Theron turned 22, she decided to invest money and celebrate her aging self in the presence of Hollywood royalty. And who better to invite to your birthday party than Leonardo DiCaprio, who was about to become globally famous for his role in the blockbuster James Cameron film Titanic. Although, he had already established his presence in Hollywood with amazing performances in The Basketball Diaries, and Romeo + Juliet.

Billy Idol & Drew Barrymore, 1984

Drew Barrymore grew up in the media industry, so it should come as no surprise that the now famous actress has been the focus of professional photographers since she was a little girl. But what else do you expect from someone who has Steven Spielberg, the legendary Hollywood filmmaker, as her godfather? In this picture, 9-year-old Barrymore is shown partying with musician Billy Idol. Although, we're sure it was a mellow, kids-appropriate version of a party.

David Bowie & Mick Jagger, Unknown Date

We're unable to confirm the date of this photograph, but it has definitely fueled the speculation that David Bowie and Mick Jagger, two of the most recognized musicians in music history, had a secret love affair which they kept hidden from the world. Judging by this picture alone, it seems the allegations may be true as the two look very comfortable sitting together on the couch with Bowie's hand on Jagger's chest. It could just be a sign of the bromance both of them shared, but we'll never know for sure!

Ozzy Osbourne, 1980s

Reddit users have found this picture of singer Ozzy Osbourne from the '80s mildly disturbing, but it does show the fun side of the legendary musician. The picture was taken by professional photographer Mark Weiss, who is known for taking some of the best pictures in the rock music industry. Ozzy is about to turn 70 years old, so this picture from a completely different time should act as a great memory to relive with his wife Sharon, whom he married in 1982, and his children.

Brad Pitt & Tom Cruise, 1994

It's always nice to see two Hollywood A-listers posing together for a photo. Especially from the photographer's perspective since he or she is able to capture a photo which brings in a lot more money than a picture of a celebrity standing alone. This one was captured at the premiere of the film Interview with the Vampire, which starred both Tom Cruise and Brad Pitt in the film—a rare combination.

Brad Pitt & Christina Applegate, 1989

Brad Pitt's relationships with Jennifer Aniston and Angelina Jolie is all everyone seems to talk about when discussing his personal life, so his brief involvement with Christina Applegate in the late '80s has been forgotten over time. It has been reported that Applegate decided to ditch Pitt and became someone else's date at the MTV Video Music Awards in 1989. We can only imagine the embarrassment Pitt must've gone through. Although, we are sure he has moved on from it now that he has a net worth of around $240 million.

Axl Rose, Steven Tyler & His Daughters Liv & Mia, Unknown Date

This picture does not come with a date either, but it's a beautiful memory of the past when the American rock music industry was booming with the sounds of Guns N' Roses and Aerosmith—the former being Axl Rose's band while the latter featuring Steven Tyler. Of course, as children of a famous father, Liv and Mia got to experience music royalty from a very young age. Their proximity to two legends should be the source of envy for many young girls who would've given anything for such a photograph.

Keith Richards, Tina Turner & David Bowie, 1983

If you are a fan of music, then pictures like this should be pinned on your Pinterest account for one obvious reason: they are iconic and offer perfect history lessons for future generations who would want a peek into the kind of lifestyle lived by their music ancestors. In this picture, music legends Tina Turner and David Bowie seem to be attempting a rather risky move of drinking alcohol from a bottle simultaneously. We bet some of it must have spilled on their outfits.

Cher & Gregg Allman with Sisters, 1975

In 1975, the only wedding which mattered was that of Cher and Gregg Allman, even though it eventually ended sooner than expected in 1979. But both of them looked absolutely graceful wearing all-white clothing, although it could just be the monochromatic photograph which shows it this way. Standing beside them in this picture are their sisters who look very happy to see their siblings getting hitched. Allman passed away in 2017 due to issues with his liver.

Matt LeBlanc & Matthew Perry, 1990s

Just like Courtney Cox and Jennifer Aniston, Mathew Perry and Matt LeBlanc also developed a friendship which has survived for years after the show ended. Although both of them don't get to spend as much time with each other as they did while filming Friends, that has not had a negative impact on their friendship with each other. This picture is probably from the '90s while they were filming the earlier seasons of the show, as both of them look much younger with no wrinkles on their faces.

Johnny Depp & Sherilyn Fenn, 1986

The '80s was a completely different era, a fact proved by the very different personas portrayed by the Hollywood celebrities we follow today at that point in time. Case in point: Johnny Depp and Sherilyn Fenn. Both of them met at the set of Dummies, a short student film made for the American Film Institute, which probably did not give the two budding actors a lot of dividends (if any) for their work. At one point, the two even got engaged. However, their relationship ended sometime in 1988.

Whitney Houston & Michael Jackson, Unknown Date

What makes this picture truly a trip down memory lane is that both these legendary musicians are no longer in this world. Michael Jackson and Whitney Houston are recognized as two revolutionary artists, not only because they produced amazing music but also because both of them broke barriers for other black musicians to enter the industry. They also collaborated on a number of occasions throughout their careers, giving birth to a friendship which lasted until Michael's death.

Jack Nicholson & Anjelica Huston, Unknown Date

Jack Nicholson and Anjelica Huston had an on and off relationship for a very long time, around 17 years or so, which has to be the longest relationship Jack has maintained throughout his life. As for Anjelica, she married after breaking up with Jack. However, that ended with the death of her husband Robert Graham in 2008. Even though he has had rocky relationships, Nicholson has still managed to have five children, who will be inheriting money from the actor eventually.

Leonardo DiCaprio & Kate Moss, Unknown Date

Nobody likes the paparazzi. Well, nobody except for Kate Moss apparently, as she can be seen in this photograph giving the most perfect smile to the camera as Leonardo DiCaprio looks rather annoyed by all the attention. Leonardo has been known to engage with supermodels especially during the '90s, and it seems Kate Moss was his company during 1993. This picture is probably from NYC where the two reportedly shared their brief romance.

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