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Grant's breakthrough came with the leading role as Charles in Four Weddings and a Funeral (1994), opposite Andie MacDowell, a role which won him a Golden Globe Award, as well as a BAFTA Film Award for Best Actor. During the 1990s Grant established himself as a very original and resourceful actor. He played a string of characters projecting a positive mindset, showing how do you stay optimistic when you are actually worried about a cascade of troubles. Grant had his own experience as a survivor of an unfortunate episode in his private life, which he managed to overcome thanks to having a pretty damn good outlook on life.

His forte is playing characters projecting warmth and sincere happiness, with his hallmark stuttering, albeit some accused him of reprising the same character he has been playing for the past two decades. Grant's ability to show his character development within a limited screen time shines in Love Actually (2003), with his witty portrayal of a Prime Minister whose personal insecurities become intertwined with his country's international affairs, a performance that earned him a nomination for European Audience Award. His screen presence and skillful understatement takes his characters beyond the written script, thanks to his mastery of timing and effortless style.

Outside of his acting profession, Grant has been a good athlete, he played cricket and football in his younger years. He enjoys playing golf, frequently taking part in Pro-Am tournaments. He has been an avid art lover since his younger years, and has been collecting fine art, a passion he inherited from his father.