Most Expensive Celebrity Photographs Ever Sold

Reported Price: $4.1 million*
Year of Publication: 2006

When Brad and Angelina’s first child, Shiloh Jolie-Pitt, entered the world, paparazzi were more than willing to pay for the sensational first photos. The couple was more than willing to hand them over – if the price was right. 

Shiloh Jolie-Pitt First Photos @theimageculture / Pinterest.com

In the end, People put up the most cash, offering $4.1 million in order to be the first to debut the first Pitt-Jolie child. It wouldn’t be the last time photos of the family would be sold. As far as Hollywood dynasties go, Jolie and Pitt managed to create one of the largest and most lucrative ever to walk the earth. They have been featured in big publications like New York Times. 

Reported Price: $500,000*
Year of Publication: 2005

2005 was a great year for Britney Spears, who had settled down into married life with Kevin Federline and even welcomed her first child, Sean Preston. For a while, it looked like all was well and fine in Britney land, especially when People paid her $500,000 to get the first photos. 

Sean Preston Federline First Photos @katinkakarolina / Pinterest.com

The little family of three was glowing, but we all know how that story ended. The couple split not long after the birth of their second son and Britney had a very public meltdown in 2007. The clips can still be found on YT to this day, while her conservatorship is still ongoing. 

Reported Price: $500,000*
Year of Publication: 2005

It’s no secret that when Brad Pitt and Angelina Jolie got together, it caused a huge stir. Everyone thought that Pitt would be with Jennifer Aniston forever, but it wasn’t to be. When rumors started that Ang was pregnant, everyone wanted a photo. In 2005, they got one when Jolie was snapped with a visible bump. 

Angelina Jolie Visibly Pregnant @heidibeetcherphotographer / Pinterest.com

There was a bidding war, with People paying half a million to get the precious snap. The pair went on to have several more children together before splitting two years after tying the knot in 2016. Needless to say, they’re still very much in the public eye. 

Reported Price: $6 million*
Year of Publication: 2008

Jennifer Lopez is just as famous for her love life as she is for her incredible on-stage presence and musical talent. When she dated Ben Affleck in the noughties, they seemed destined to be together, but later split. Just a few months later, she was married to singer Marc Anthony. 

Max And Emme First Photos @nicolaareid / @olgiejulia / Pinterest.com

With Anthony, J-Lo welcomed twins Emme and Max in 2008. The media was chomping at the bit to publish the photos, but it was People who paid the highest amount. $6 million later and the first snaps of the kids, Max and Emme, were out there for the world to see. The Disney star made a fortune just saying “Cheese!”

Reported Price: $1 million* 
Year of Publication: 2006

Anna Nicole Smith was somewhat of a tortured soul that had a tumultuous time in the spotlight. The former Guess model and Playboy star married attorney Howard K. Stern in 2006 in the Bahamas during a lavish commitment ceremony on-board a yacht. 

Anna Nicole Smith And Howard Stern Wedding @lvlakota777 / Pinterest.com

What many didn’t realize at the time was that the marriage wasn’t actually legal as no license was obtained. That didn’t stop People from paying $1 million to the couple for the photos, which got a lot of attention. Less than a year later, Smith passed away in her hotel room in Hollywood, FL. Many documentaries have been made about her life, some of which are available to view on Amazon Prime. 

Reported Price: $3 million* 
Year of Publication: 2008 

In the early years of his successful career, Matthew McConaughey enjoyed being a lad about town, dating some of the most beautiful women in the business. Then, he met Camila Alves by chance in a bar in 2006. The rest was history. 

Levi Alves McConaughey First Photos @chanablumes / Pinterest.com | camilamcconaughey / Instagram.com

They welcomed their first son, Levi, in 2008. Needless to say, the world went wild for a peep at the happy family. OK! Magazine was more than happy to appease the masses, but it cost them $3 million to get the shoot. Camila frequently shares snippets of their family life on Instagram. 

Reported Price: $6 million*
Year of Publication: 1997

You don’t have to be a royal family expert to know that Princess Diana and Prince Charles’ divorce was messy. The media loved to publish photographs of Diana, especially when she went on holiday with her boyfriend, Dodi Al Fayed in 1997. 

Princess Diana and Lover @rfcrown / Pinterest.com

The photo was caught by a paparazzi and eventually sold to the highest bidder for $6 million. The public wanted to see it, making Diana the most profitable celebrity to photograph at that time. Sadly, she would pass away later that same year, alongside her beau. 

Reported Price: $15 million* 
Year of Publication: 2008

As the years ticked by, Angelina Jolie and Brad Pitt wasted no time in adding to their family. In 2008, they announced they were expecting twins. Having sold photos before, it seemed only right that they would sell them again, once again to People – but for a much higher amount. 

Knox And Vivienne Jolie-Pitt First Photos @elenaarsenoglou / Pinterest.com

The photos of the twins, Vivienne and Knox, cost People $15 million. In a nice twist, the couple didn’t pocket the money but put it toward their charity, the Jolie-Pitt Foundation, as well as donating very large sums to Doctors Without Borders and Global Action for Children. These Sony stars were generous.

Reported Price: $575,000*
Year of Publication: 2006

Gwen Stefani has been part of the public consciousness for years, not just for her music but for her romantic entanglements too. In 1995 she met and fell in love with Gavin Rossdale when they performed together. Nine years later, they welcomed their child, Kingston. 

Kingston James McGregor Rossdale First Photos ©Marcel Thomas / Gettyimages.com

Photos went to the highest bidder, which turned out to be OK! Magazine who paid $575,000 for the privilege. They welcomed two more sons together before going their separate ways. Gwen later got together with Blake Shelton. 

Reported Price: $85,000*
Year of Publication: 2012

Once one of Nickelodeon’s shining stars, Amanda Bynes was once a stable child actress. Sadly, she began battling her own demons around 2012 and was often pictured acting strangely. When she exited the gym she was quickly photographed. 

Amanda Bynes Coming Out of the Gym @TMZ_News / Pinterest.com

In no time at all, the photo was sold for a whopping $85,000. Bynes’ behavior would only become more bizarre over the coming years, resulting in arrests, and more. Bynes’ struggles were likened to that of Britney Spears several years earlier, but thankfully she was able to get through it and come out the other side. 

Reported Price: $1.5 million*
Year of Publication: 2008

Jessica Alba was a highly popular actress in the noughties thanks to starring roles in movies like Sin City. When she filmed Fantastic Four in 2004, she met her future husband, Cash Warren. The two immediately hit it off, married, and welcomed their first daughter Honor Marie in 2008. 

Honor Marie Warren First Photos @justinfeed / Pinterest.com

OK! Magazine was determined to publish the exclusive photos so shelled out a fortune to get them. $1.5 million later and the pictures appeared in the July issue of the publication, much to the delight of readers everywhere. Alba doesn’t act as much these days, but she does have a very successful business with the HNST 

Reported Price: $1.5 million* 
Year of Publication: 2008

Christina Aguilera came up around the same time as Britney Spears, so it’s only natural that people around the world were keen to know what was going on in her personal life. Publications knew that. In 2008, when she gave birth to her son Max, People paid $1.5 million for the exclusive first photos. 

Max Bratman First Photos @mireyd_27 / Pinterest.com

In doing so, Aguilera joined the ranks of tons of other celebs that made a fortune by selling photos of their kids. She went on to have more children, although her marriage to Ma’s father didn’t last.  

Reported Price: $500,000*
Year of Publication: 2005

Fans were so shocked that Brad Pitt left Jennifer Aniston to be with Angelina Jolie that the press were desperate to get the first photo of them together. It wasn’t long before US Weekly found the winning shot of the couple on vacation with Angelina’s son, Maddox. 

Angelina Jolie And Brad Pitt Together @michalakmarzena230 / Pinterest.com

Brad was still technically with Jennifer Aniston at the time according to public knowledge, which made the photos even more sensational. US Weekly had to pay $500,000 for the photos, but it was well worth it considering how many copies of the magazine they sold in the end.