The Life and Loves of Leonardo DiCaprio

Basketball Babe

Even though DiCaprio was branching out into a variety of unconventional roles, he was also still making a name for himself as somewhat of a heartthrob—both on and off-screen.

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For example, in his 1994 movie The Basketball Diaries, he appeared as a young man struggling with addiction—a challenging and serious role. But behind the scenes, he was playing a far more lighthearted part—that of boyfriend to his co-star Brittany Daniel! After one particularly saucy scene between the two in the film, it was rumored that they’d taken their encounter off-screen, too.

Bijou Phillips

Another high-profile beauty that DiCaprio was linked with around this time was model and actress Bijou Phillips.

Phillips is probably best known for her modeling work for Calvin Klein and Vogue Italia, and her role as Lucy Carlyle on the Fox series Raising Hope—as well as being the daughter of musician John Phillips. Phillips and DiCaprio were rumored to be an item throughout much of 1998, being spotted together on numerous occasions. We wonder what Mr. Phillips thought of his daughter’s superstar romance!

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