1974 – Jack Nicholson and Anjelica Huston

Anjelica Huston and Jack Nicholson might be the most prominent stars in Hollywood, but they are perhaps the most challenging celebrity relationship in the industry. Anjelica and Jack’s love was apparent from how they looked nearly fifty years ago at his birthday celebration in 1973. The two struck up a critical bond and spent the evening dancing together, and eventually started dating a few days after the party. The topic of marriage came up at different points during their relationship, but neither seemed to feel the desire simultaneously.

Later on in their romance, Anjelica discovered that pursuing one of Hollywood’s most pursued stars was challenging. It became all the more challenging by the notion that women were constantly vying for his attention. After they separated respectively, Anjelica, with her memoir, said that “I was a child of the 60s and to a degree regarded marriage as a form of bondage.”