10 Most Toxic Hollywood Relationships Ever (4 of 6)

Madonna and Sean Penn

These two looked like an edgy ’80s power couple while in reality being a powerful chaos magnet. They married in 1985 and quickly became famous for rough fights and domestic disputes. One incident landed Madonna in the hospital, and another resulted in felony domestic assault charges for Penn that were later reduced. By 1989, the fairytale was over, and the divorce papers were signed.

Selena Gomez and Justin Bieber

Selena Gomez and Justin Bieber’s on-again, off-again romance became one of Hollywood’s most watched—and most exhausting—love stories. What started as a teenage fairy tale quickly evolved into a cycle of intense reunions, public breakups, cryptic social media moments, and emotional whiplash that played out in real time for millions of fans. Their relationship blurred the line between passion and instability, fueled by fame, youth, pressure, and unresolved personal struggles on both sides. In the context of Hollywood’s most toxic relationships, Gomez and Bieber’s dynamic stands out not for malice, but for how deeply entangled, draining, and difficult it became to let go.