The Shady Celeb Who Admittedly Couldn't Stand Princess Diana

Despite her reputation as the caring and approachable "People's Princess," the late Princess Diana wasn't beloved by everyone. Diana's relationship with the royal family was notoriously shaky, particularly once her marriage to Charles, then the Prince of Wales, began to crumble. She also fell out with famous friends like Elton John (who subsequently performed at Diana's funeral). But the iconic royal was a particular target of scorn for an outspoken celebrity known for her finely sharpened wit. At the 2013 Just for Laughs Festival in Montreal, Joan Rivers (she of the endless plastic surgeries) riffed on the equally iconic princess. "I hated her," the comedian stated bluntly (via YouTube). "You know why I didn't like her?  'Cause she didn't know when the good times were." 

Rivers poked fun at Diana's gloomy attitude despite being a privileged member of the royal family. The former "Fashion Police" co-host just couldn't understand why such a gorgeous, wealthy, and slim young woman with "a husband that didn't want to sleep with her" could possibly be miserable. "She had a crown!" Rivers exclaimed. "Do you understand that if you had a crown, you could go back to any class reunion for the rest of your life? [...] They say, 'How you doing?' You say, 'Check my hat! That's how I'm doing — better than you!'" 

Joan Rivers on Princess Diana.

Do you agree with her take? pic.twitter.com/33CBvdkPd8

— Queen Esther (@XOQueenEsther) February 12, 2026

It should be noted that Diana wasn't the only famous person to get roasted by the comedy legend that night. Rivers also took aim at Taylor Swift (she suggested that the singer's personal hygiene was responsible for her many breakups) and at "Miss Butter Queen" Adele, whom she claimed was threatening to sue her for joking about her weight.

Joan Rivers' send-up of Princess Diana notably also included a nod to her most famous piece of jewelry. Diana's engagement ring was a perfect fit for Catherine, Princess of Wales, for both its style and sentimental value as a remembrance of the mother-in-law she never knew. Rivers, however, saw it a different way. Portraying heir apparent William, Prince of Wales, she envisioned him saying, "'Darling, I love you very much. I want you to have my mother's engagement ring," adding, "My mother and father hated each other from the very beginning." The comedian went on to reference Diana and Charles's infidelities and the princess's tragic death, before miming William slipping the ring onto Kate's finger and telling her, "Good luck!" 

Though the audience in Montreal laughed along with her, Rivers' pull-no-punches style sometimes backfired. A year before Just for Laughs, the comedian hosted a British-themed episode of "Fashion Police" in which she cracked, "If you want to go to Paris, fly; don't take the tunnel," (per ABC News). The reference to the People's Princess' fatal car crash elicited shock and anger from U.K. viewers, but that didn't prompt Rivers to sand down her pointed jokes. In fact, she continued utilizing her signature brand of insult comedy right up until her death in September 2014. 

At least one member of the royal family appreciated the comedian's style, however. King Charles III didn't mind Rivers' jokes about his ears; far from it, he often invited her to perform at royal events. Rivers was even a guest at Charles' wedding to future Queen Consort Camilla Parker Bowles.