The “Orange Is the New Black” and “Crazy Beautiful” star Taryn Manning met Holliann Hartman in 2007 when she was working as her makeup artist. Similarly to the way you form a close connection with a person whose job requires close physical proximity (anyone poured their heart out to their hairdresser lately?), the two quickly became good friends, and Manning hired her as a personal assistant full-time.
Unfortunately, that didn’t last very long, as five years later, the two had a pretty bad fight. Even though details weren’t published, Manning was charged with assault and spent some time doing community work after being sentenced.
Gilly Iyer – Jennifer Lopez
Gilly Iyer worked as Jennifer Lopez’s assistant for several years, becoming a close friend to the pop star. Unfortunately, and for reasons that remain unknown until this day, Gilly and Jennifer had a falling out that ultimately ended in Iyer resigning in 2013.
It sounds like the number one occupational hazard of trusting another person to manage another person's personal affairs. To make matters worse, Iyer immediately started working for Mariah Carey, who, according to the press, is J.Lo’s archnemesis. It seems the Latina diva didn’t make much of a fuss about it, as she hired another P.A. days later.
Jessica Labrie – Courtney Love
It isn’t surprising to learn that Courtney Love was sued by her assistant; after all, Kurt Cobain’s ex isn’t exactly known for being levelheaded. In 2010, Jessica Labrie started working for Love as her P.A. and was promised that her degree at Yale University (which couldn't have been cheap) would be completely paid for.
Two years, and a whole lot of drama later, Labrie sued the rockstar for unpaid wages. It seems she was never paid for any of her work, which included insane tasks – like being asked to falsify legal documents – which Labrie obviously refused to do.
Cheyne Thomas – Miley Cyrus
Cheyne Thomas was Miley Cyrus’s assistant in 2010, and the two were as close as can be, elevating their relationship from the status of boss and worker to an actual friendship. The two girlfriends traveled, partied, shopped, and did everything together. In 2014, they even got matching tattoos as a sign of their forever friendship.
But all that came crashing down in 2016, when Cyrus got back together with Liam Hemsworth. Miley and Liam were known for the on-again off-again nature of their relationship. Nobody knows what happened at that specific time, or what caused the two friends to stop talking to each other. What a drama!
Terrence Smalls – Justin Bieber
Nowadays, you don’t hear much about pop superstar Justin Bieber, other than he’s married to the stunning Hailey Bieber. But a few years ago, this Canadian singer had a reputation for being particularly difficult to work with. Of course, a celebrity superstar like Bieber needs a right hand, and his was called Terrence Smalls.
He was Bieber’s assistant for two years and made an annual salary of around $70,000. However, Smalls was fired after he was caught in an Australian airport with 13 grams of an illicit substance. To boot, the police were also after Bieber since, apparently, he had nearly destroyed his hotel room after a night of partying. Yikes!