Leonardo DiCaprio Has Dated All Of Hollywood's Most Beautiful

Claire Danes may have a high-profile husband of her own nowadays, but back when she was a teenager, she was the on-screen love of Leonardo DiCaprio. The rumors about their on-set relationship run the gamut. Some sources claim that though Claire was only 16, she found 22-year-old Leo unprofessional. That's a stark contrast to her recent confession that she had a crush on him while they were filming Romeo + Juliet. Danes implies nothing happened, but it's hard to know for certain.

Leo may not have hit peak movie star back in 1995, but he certainly knew how to find the biggest names on the runway, even when he was just hitting adulthood. Though he and Naomi Campbell never seemed to have a serious relationship, the rumor back in the day was that the two enjoyed some sort of fling, at least for a brief period of time. At that age, it's normal to experiment with your love life, though it seems Leo hasn't quite left those days behind.

Natasha Henstridge may not have been the first model Leo was linked to, but given her acting ambitions, it's no wonder the relationship wasn't built to last. Around the time Leo and Natasha were introduced to one another, Leo was on the brink of becoming an A-list star following the release of Titanic, while Natasha had experienced her first taste of success as an actor, rather than a model. The two never quite went public with their romance.

It seems that as a young man, Leo was slightly more experimental when it came to his choice of women. Bijou Phillips in the 1990s wasn't exactly the type of leggy blonde model that Leo would prefer in his later years. However, it seems their relationship, no matter how short it may have been, proved advantageous. Phillips may have come from a showbiz family, but it was Leonardo DiCaprio who connected her to the director that would cast her in her first film, Black and White.

Trishelle Cannatella might have faded into obscurity shortly after her time on The Real World came to an end, but if the rumors are true, then at least Leo DiCaprio noticed her. During what must have been an off period with Gisele, Leo was linked with one of the first reality stars to make waves with the public. Of course, given Leo's relationship status at the time, we only have Trishelle's word to go off of.