Leonardo DiCaprio in 1989
Leonardo DiCaprio in 1989
Leonardo DiCaprio in Parenthood in 1990
Leonardo DiCaprio in the ’80s
Leonardo DiCaprio on Growing Pains on Sept. 28, 1991
Leonardo DiCaprio in 1993
Leonardo DiCaprio at the 66th annual Academy Awards in Los Angeles on March 21, 1994
Leonardo DiCaprio and Dennis Hopper at the Red Rock West party in 1994
Leonardo DiCaprio in New York City in 1995
Leonardo DiCaprio with Mark Wahlberg in 1995
Leonardo DiCaprio in The Basketball Diaries in 1995
Leonardo DiCaprio in Total Eclipse in 1996
Leonardo DiCaprio at the premiere of Romeo + Juliet in Hollywood on Oct. 27, 1996
Leonardo DiCaprio with Claire Danes in Romeo + Juliet in 1996
Leonardo DiCaprio with Kate Winslet in Titanic in 1997
Leonardo DiCaprio in The Man in the Iron Mask in 1998
Leonardo DiCaprio in The Beach in 2000
Leonardo DiCaprio at the Concert for New York City on Oct. 20, 2001
Leonardo DiCaprio promoting Gangs of New York in Cannes, France on May 21, 2002
Leonardo DiCaprio at the Catch Me If You Can Los Angeles premiere on Dec. 16, 2002
Leonardo DiCaprio at the Gangs of New York premiere in Paris on Jan. 6, 2003
Leonardo DiCaprio at the London premiere of Catch Me If You Can on Jan. 27, 2003
Leonardo DiCaprio on Nov. 20, 2004
Leonardo DiCaprio at The Aviator press conference in Los Angeles on Nov. 20, 2004
Leonardo DiCaprio at the 57th annual DGA Awards Dinner in Beverly Hills on Jan. 29, 2005
Leonardo DiCaprio with Gisele Bundchen at the 77th Academy Awards in Hollywood on Feb. 27, 2005
Leonardo DiCaprio in Los Angeles on Nov. 16, 2006
Leonardo DiCaprio with Jennifer Connelly at the Blood Diamond Los Angeles premiere on Dec. 6, 2006
Leonardo DiCaprio at the premiere of The 11th Hour in Hollywood on Aug. 8, 2007
Leonardo DiCaprio at the Paris premiere of Body of Lies on Nov. 3, 2008
Leonardo DiCaprio with Kate Winslet at the Los Angeles premiere of Revolutionary Road on Dec. 15, 2008
Leonardo DiCaprio at the 20th anniversary of the Palm Springs International Film Festival Awards Gala on Jan. 6, 2009
Leonardo DiCaprio with Kate Winslet at the 66th annual Golden Globe Awards in Beverly Hills on Jan. 11, 2009
Leonardo DiCaprio at the J. Edgar opening night gala at the AFI FEST 2011 in Hollywood on Nov. 3, 2011
Leonardo DiCaprio with Tobey Maguire at the photocall for The Great Gatsby at the 66th annual Cannes Film Festival on May 15, 2013
Leonardo DiCaprio with Kate Winslet in Beverly Hills on May 22, 2013
Leonardo DiCaprio at the 71st annual Golden Globe Awards on Jan. 12, 2014
Leonardo DiCaprio at the 86th annual Academy Awards in Hollywood on March 2, 2014
Leonardo DiCaprio filming The Wolf of Wall Street in New York City on Sept. 25, 2012
Leonardo DiCaprio at the Screen Actors Guild Foundation 30th Anniversary Celebration in Beverly Hills on Nov. 5, 2015
Leonardo DiCaprio with former President Barack Obama at the White House on Sept. 25, 2016
Leonardo DiCaprio with Brad Pitt at the Cannes premiere of Once Upon a Time in Hollywood on May 21, 2019
Leonardo DiCaprio…