Believe it or not, Donald Trump’s friendship with Jeffrey Epstein is not the only creepy relationship in the world of fame. It’s top of the list in terms of strange, but the couple are not alone. As National Friendship Day approaches, we take a look at some weird friendships.
A History Collection feature has delved into around a dozen such ‘dark friendships’, where the glittering fame of the celebrity is tarnished by the infamy of their companion.
Take Selena Gomez and Justin Bieber, whose on-and-off friendship and romance unfolded under intense public scrutiny. As Bieber’s frequent arrests and erratic behavior made headlines, Gomez found herself enmeshed in chaos—even though she was often framed as the innocent party compromising her own image through loyalty.
I’m gonna post this every day so nobody forgets exactly who Pedophile Trump is and why the Epstein files have suddenly disappeared. pic.twitter.com/2SV5aTkgJl
— Morgan J. Freeman (@mjfree) July 25, 2025
Then there’s Charlie Sheen and Heidi Fleiss. The actor’s friendship with the notorious “Hollywood Madam” dragged him into scandal too, turning late-night tabloid fodder into courtroom intrigue and forever entwining his public persona with her legal controversies.
Reality star Nicole Richie also finds mention for her friendship with Jonathan Cheban, often accused of dodgy business deals and questionable PR stunts. The pair’s visibility in reality media served to highlight how fame can blur the lines between genuine bonds and mutual self-promotion.
Taylor Swift and Scooter Braun’s relationship went from distant industry ties to a very public feud. Trouble erupted when Braun bought Big Machine Records, giving him ownership of Swift’s first six albums.
6 years ago today, Scooter Braun’s company acquired Taylor Swift’s master recordings.
This acquisition was part of a larger sale of Big Machine Records to Ithaca Holdings, which ignited a feud between Swift and Braun, as she had been trying to gain ownership of her masters for… pic.twitter.com/x0Bojo583H
— Pop Hive (@thepophive) June 30, 2025
Swift accused him of years of behind-the-scenes bullying and called the deal her “worst case scenario.” Their fallout highlighted issues of power and control in the music industry, with Swift reclaiming her work by re-recording her albums. What started as a business connection turned into a symbol of an artist fighting back.
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