Bijou Phillips: The Beginning
Age: 24
Year: 1998
Leonardo DiCaprio and Bijou Phillips’ relationship started in 1998, when Phillips, then 18, was just starting her journey in Hollywood. Their romance quickly drew public attention, and DiCaprio was often seen as a mentor to the budding model and actress.

He played a significant role in launching Phillips’ career by introducing her to influential industry figures, including helping her land one of her first film roles in Black & White (1999) by connecting her with director James Toback.
