Remember When: A Look Back at the Biggest Celebrity News of 2019

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Kylie Jenner Jordyn Woods
Photo: Courtesy of @kyliejenner

From tragic deaths and surprising break-ups to prison sentences and lawsuits, these were the 10 biggest celebrity news of 2019.


An Affair to Remember

Whether you keep up with the Kardashians or not, there was no escaping the fallout from the affair that rocked the famous family in February. Jordyn Woods (Kylie Jenner’s best friend) and Tristan Thompson (Khloe Kardashian’s boyfriend) were spotted kissing at a party. Given Woods’ status as a trusted family friend and Thompson’s previous betrayals, the scandal ended the entire Kardashian-Jenner clan’s relationship with both.


Long Live the Kaiser

On February 19, legendary designer Karl Lagerfeld passed away from complications due to pancreatic cancer at the age of 85. With 60 years in the fashion industry, his imprint was immense and impossible to quantify. His “right and left hand” Virginie Viard was instantly tapped to take up his mantle at Chanel, while Silvia Venturini Fendi continued on his work at Fendi. Although he is gone, we predict echoes of his astonishing body of work and creative spirit will continue to live on in fashion for decades to come.

Karl Lagerfeld Karl For Ever
Photo: Courtesy of @chanelofficial

What Goes Around

From his illegal marriage to underage singer Aaliyah to criminal allegations of child pornography and abuse, R. Kelly’s despicable behavior has been well-documented. However, 2019 was the year that the consequences of his actions finally took hold.

After the January 2019 docuseries Surviving R. Kelly aired (in which multiple women came forward with allegations against the singer), the public became widely aware of the extent of his pathological criminal conduct. He was indicted on 10 counts of aggravated criminal sexual abuse in February, and he was arrested on federal charges in July. Kelly now faces a total of 18 federal counts, and he will remain in jail until his 2020 trial.


Leave Britney Alone

Britney Spears’ career has been a rollercoaster of highs and lows. After her tabloid romance with Kevin Federline in 2006, the popstar unraveled, causing her to lose custody of her children. Her father and attorney Andrew Wallet, meanwhile, assumed conservatorship of her estate. One of the driving forces behind her breakdown was her predatory manager Osama “Sam” Lutfi, who was eventually removed as a controlling force in her life.

In 2019, Lufti was back again, churning the rumor mill about her mental health. He is the author of the #freebritney hashtag that falsely claimed Spears was being held in a mental health institution against her will. After her incredible road to recovery, Spears was having none of that, and addressed the rumors personally via Instagram.


View this post on Instagram


I wanted to say hi, because things that are being said have just gotten out of control!!! Wow!!! There’s rumors, death threats to my family and my team, and just so many things crazy things being said. I am trying to take a moment for myself, but everything that’s happening is just making it harder for me. Don’t believe everything you read and hear. These fake emails everywhere were crafted by Sam Lutfi years ago… I did not write them. He was pretending to be me and communicating with my team with a fake email address. My situation is unique, but I promise I’m doing what’s best at this moment 🌸🌸🌸 You may not know this about me, but I am strong, and stand up for what I want! Your love and dedication is amazing, but what I need right now is a little bit of privacy to deal with all the hard things that life is throwing my way. If you could do that, I would be forever grateful. Love you ❤️❤️❤️

A post shared by Britney Spears (@britneyspears) on


Full House to Big House

In March, news broke that several celebrities had been arrested because of a bribery scam that involved paying large sums of money to get their children into prestigious universities around the USA. Lori Loughlin (who played Aunt Becky on the popular 90s show Full Houseand her husband Mossimo Giannulli were among those accused, as was Felicity Huffman of Desperate Housewives fame. The college admissions scandal attracted international attention as the cases proceeded, resulting in Huffman’s two-week prison sentence, while Loughlin and her husband pleaded not guilty and are still embattled in court.


See the Light

From feuding with Taylor Swift to declaring that slavery was a “choice”, Kanye West is no stranger to controversy, but 2019 might have been his most outrageous year yet. After infuriating his fan base with his refusal to stop wearing a “make America great again” hat and his constant support of Donald Trump, the rapper leaned into the conservative messaging by radically reinventing himself as a Christian evangelist. 

With the release of his first gospel album Jesus Is King, West made his first appearance atop the Billboard’s Christian and Gospel album charts, and recently appeared at America’s most prominent megachurch as a guest speaker. Recently, he created an opera called Nebuchadnezzar based on a king from the Bible. Where his career goes from here is anyone’s guess.


Royal Pains

Prince Harry and Meghan Markle have had a tough year. Not only did Markle give birth earlier this year, but she and her husband have been relentlessly hounded by the media. Rumors have circulated that the two don’t get along with Prince William and Kate Middleton – and that’s one of the nicer rumors. 

For his part, Prince Harry has gone out of his way to protect his wife, calling out the tabloids for their allegedly illegal pursuit of negative stories about the couple. Recently, Buckingham Palace confirmed the filing of claims regarding illegal interception of voicemail messages, while Markle has sued The Mail on Sunday for breach of privacy and copyright infringement. Legal actions aside, all the scrutiny and negative attention have taken a massive toll on the couple, with Prince Harry coming forward to speak about his struggles with mental health. It is now a core philanthropic issue for Duke and Duchess of Sussex.

Photo: Courtesy of Getty Images

Achy Breaky Heart

One could practically make a full-time job of following and documenting the extreme ups and downs of Miley Cyrus’ post-divorce relationships. After the popstar and her husband of eight months, Liam Hemsworth, parted ways in August, she instantly jumped into a relationship with her friend Kaitlynn Carter. After that fizzled, she was all over Instagram with PDA-filled displays with musician Cody Simpson.


Chemistry Matters

She was engaged to Christian Carino, he was in a longterm relationship with Irina Shayk, but somehow, everyone on earth was convinced that Lady Gaga and Bradley Cooper were destined to be together. As the co-stars of A Star Is Born, the two celebrities shared so much on-screen chemistry that people quickly started ‘shipping them IRL. The rumors worked out to be a boon for the success of the film, and it turns out that they decided to make it work for them – rather than against. 

After an electrifying live performance of the film’s hit single “Shallow”at the Academy Awards this year, Lady Gaga and Cooper were consumed by a tidal wave of social media excitement. The fact that both of them were also single soon after the performance only served to stoke the flame of affair rumors. However, in November, Lady Gaga revealed that it was all an act, saying, “We wanted people to feel that love at the Oscars. We wanted it to go right through the lens of that camera and to every television that it was being watched on. And we worked hard on it, we worked for days. We mapped the whole thing out – it was orchestrated as a performance.”


Vlogger vs. Vlogger

Prior to 2019, James Charles was a name only known in very specific circles. As a famous YouTube makeup artist, he was well-known to beauty fans and beauty fans only, but after he walked the pink carpet at the Met Gala and a rather public feud with fellow beauty vlogger Tati Westbrook, his notoriety exploded.

After Westbrook’s call-out video – in which she accused Charles of betrayal – he hemorrhaged followers and issued a tearful apology for the behavior that caused his fellow beauty buffs to turn against him. But like in most cases of #cancelculture, the backlash against Charles quickly subsided and he’s back on top once again, with recent news that he is teaming up with YouTube to debut a reality show competition slated for 2020.

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