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When Heatherton moved on to Australian musician Felix Bloxsom, she told Daily Mail that she and Di Caprio remain friends.Toni Garrn – From around May 2013 to December 2014, Di Caprio dated model Toni Garrn.Di Caprio found great success early in his career and was nominated for an Academy Award for his role in 1993’s Di Caprio has continued to be one of Hollywood’s most sought-after leading men and has starred in films such as Inception, The Great Gatsby, The Wolf of Wall Street and The Revenant.He has been nominated for a Best Actor Academy Award four times, and won his first in 2016 for his role in The Revenant.
Before Tom Brady, Gisele Bündchen dated Leo for five years, but ended it in 2005.
Romantically, Leo has been tied with several models and actresses over the years, dating the likes of Gisele Bundchen, Bar Refaeli, Blake Lively and Kelly Rohrbach.
Leo's 1995 rumored fling with Naomi Campbell reportedly fizzled fast, but they became good friends.
Di Caprio”s movie debut came in 1991 in the low budget horror, “Critters 3.” In the early 1990s, he also starred opposite Robert De Niro in “This Boy”s Life”, and “What”s Eating Gilbert Grape” with Johnny Depp, a role which earned him his first Oscar and Golden Globe nominations.
Di Caprio continued to pursue diverse roles and in 1997 his career propelled to the stratosphere with the leading role in James Cameron”s “Titanic” opposite Kate Winslet, the first movie to reach a billion dollars at the box office.