Things ended with Leo, and she moved on to costar Elijah Wood.
Di Caprio's portrayals of Howard Hughes in The Aviator (2004) and Hugh Glass in The Revenant (2015) won him the Golden Globe Award for Best Actor – Motion Picture Drama, and his role as Jordan Belfort in The Wolf of Wall Street (2013) won him the award for Best Actor – Motion Picture Musical or Comedy.
Although a source told The New York Daily News that Kristen was "the love of his life," she dumped him because of his immaturity and "posse of young model-hounds."The daughter of singer John Phillips, Bijou dated Leo in 1998.
He hooked her up with her first big Hollywood connection, director James Toback, who cast Bijou in his film Black and White.
But while a pretty face and slim figure are nothing unusual in Hollywood circles, the next requirement is rather more niche - they must be able to ride a bike...Leonardo Di Caprio is ready for adventure at a moment's notice.
The 42-year-old star was snapped during a visit to Thailand's Ayutthaya Historical Park while he vacationed in the Southeast Asian nation.