Sean Penn Oscar: did actor go to Ukraine - why did Mystic River star give President Zelensky the award?

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Actor and political activist Sean Penn gifted one of his Oscar statuettes to Ukrainian President Volodymyr Zelensky during a visit to Kyiv

Hollywood actor Sean Penn paid Ukrainian president and fellow screen star Volodymyr Zelensky a visit this month, and presented him with one of his own Oscar statuettes. Penn has been a vocal supporter of Ukraine since the beginning of the illegal Russian invasion and has built a strong relationship with the country’s president. Penn presented Zelensky with the statuette as a symbol of his continued support.

Sean Penn won his second Oscar for MilkSean Penn won his second Oscar for Milk
Sean Penn won his second Oscar for Milk | Getty Images

How many Oscar does Sean Penn have?

The actor has won two Academy awards, known as Oscars, over his decades-long career in the film industry. Penn won his first Oscar for Best Actor in the 2003 film Mystic River - a dark drama about three childhood friends whose lives are riven by abuse and trauma.

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Penn won his second Oscar for Best Actor for the 2008 biopic Milk, about Harvey Milk, California’s first openly gay elected official. The statuettes are cast in bronze and electroplated in 24-karat gold. It is not clear which of his two Oscars Penn gave to Zelensky.

Penn was nominated for three Best Actor Oscars before winning his eventual win for Mystic River. These were for the roles of Matthew Poncelet in the 1996 prison drama Dead Man Walking, Emmet Ray in the 1999 mockumentary The Sweet and Lowdown, and Sam Dawson in the 2001 drama I Am Sam.

Why did Sean Penn give Volodymyr Zelensky an Oscar?

Sean Penn visited the Ukrainian capital Kyiv on Tuesday 8 May - it was his third visit to the country since the invasion of Ukraine by Russia began in February this year. Like Penn, Zelensky has previously worked as an actor - starring in several Ukrainian comedy films and even playing the President of Ukraine in the political satire Servant of the People - he became the country’s real-life president two months after the final episode aired.

In a video, shared by Anton Gerashchenko, advisor to the minister of internal affairs of Ukraine, Penn tells Zelensky: “This is for you. It’s just a symbolic silly thing, but if I know this is here then I’ll feel better and strong enough for the fights. When you win, bring it back to Malibu, because I’ll feel much better knowing there’s a piece of me here.”

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Zelensky awarded Penn the Order of Merit of the III degree for his support of Ukraine during the conflict - the honour is given to individuals for outstanding achievements in economics, science, culture, military or political spheres. Responding to receiving the honour, Penn said: “There are three places in the world that all my pride will be, the place where my daughter was born, the place where my son was born and this. Thank you.”

Did Sean Penn break Academy rules?

According to the Academy Award regulations, “award winners shall not sell or otherwise dispose of the Oscar statuette, nor permit it to be sold or disposed of by operation of law, without first offering to sell it to the Academy for the sum of $1.00”.

The rule was put in place in 1951 to preserve the integrity of the Oscar symbol and to prevent actors from pawning their awards. As Penn has only lent Zelensky his Oscar as a symbol of goodwill, and has asked him to return it to him on the event of Ukraine’s victory, he hasn’t breached the Academy rules.

Penn had stated back in March 2022 that he would smelt both of his Oscars if the Academy did not offer Zelensky an opportunity to speak at the awards ceremony held that month. The Academy did not invite the Ukrainian president to speak at the ceremony, but a formal statement expressing support for Ukraine was made during the broadcast. In the end, Penn did not smelt either of his Oscars - this likely would have been a breach of Academy rules.

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