▲

Vladimir Putin is one of the most controversial world leaders of our days. But for many years he was simply the prime minister or president of Russia, and as such he met many famous figures. From Hollywood stars to sports personalities, Putin has met numerous celebrities over the years.

Browse through the following gallery and see who crossed paths with the Russian head of state.

▲

Sean Penn was also in Russia at the time, for a screening of his movie 'The Pledge' (2001), which starred Nicholson, and also met Putin at the same party.

▲

The actor met the Russian president in Saint Petersburg, where both attended a conference on the endangered Siberian tiger. Two of DiCaprio's late grandparents were actually Russian.

▲

This was no smooth trip though. The actor's first plane underwent an emergency landing, and his second had to stop due to strong headwinds. Putin admired DiCaprio's bravery, calling him a muzhik, which translates to "real man." "A person with less stable nerves could have decided against coming, could have read it as a sign—that it was not worth going," Putin said.

▲

The Hollywood star met the Russian president in June 2001, at a party during the Moscow International Film Festival.

▲

Putin reportedly told Nicholson that 'One Flew Over the Cuckoo's Nest' (1975) was one of his favorite movies. The actor apparently returned the compliment by offering Putin a producing job in a future film.

▲

McCartney performed for the first time in Russia in 2003. The show took place in Moscow's iconic Red Square. The former Beatle met the president during his visit to the country.

▲

Not only did McCartney meet Putin, but after learning that he wouldn't be able to attend his show, the musician performed 'Let it Be' on the piano just for Putin. "I hadn't been so nervous in years—it was my first gig in Russia, and it was just me, Heather and Putin," he recalled.

▲

"He was fabulous. We had a quite intimate conversation about his life, which was quite refreshing," McCartney said about his meeting with Vladimir Putin.

▲

Putin didn't quite comply with President Barack Obama's request for Russia to stop supplying weapons to Syrian President Bashar al-Assad during the country's civil war. Luckily, Steven Seagal came to the rescue as a diplomatic intermediary between Russia and the US.

▲

The actor and Putin met a few times and bonded over their mutual love of martial arts and Russian heritage.

▲

"I would like to think I know him well, but suffice it to say I know him well enough to say that he is one of the greatest world leaders, if not the greatest world leader, alive today," Seagal said in 2013.

▲

"He cares more about Russia than anybody I know, and he's not afraid to stand up and do what needs to get done," he added.

▲

In 2014, Stone directed a documentary called 'Ukraine on Fire,' about the alleged CIA involvement in the Ukrainian revolution at the time. The doc included commentary from Putin. Then in 2017, 'The Putin Interviews' came out, which included numerous interviews with the Russian president and footage about Putin's life.

▲

"This has been a defensive maneuver from the Russian side. The United States and its allies in NATO have been provoking Russia, have been using Ukraine as bait," said Stone just weeks before the conflict started.

▲

The actor was actually a boxer before he made it in Hollywood. In 2014, he stepped into the ring again in Moscow. He spent some time in Russia preparing for the fight and met Putin during this period.

▲

"I actually met Putin. And I had a good feeling about him and I liked him and we got along very well. He seemed like a really okay guy to me," Rourke said in 2018.

▲

It's safe to say that Putin loves a good action movie star, and Van Damme is no exception. The two met during the actor's visit to Russia in 2010.

▲

While sitting next to the president, Van Damme reached for his bag, which was placed under his seat. And then, the actor recalls, "As soon as I go to my bag, I've got 20 security guys coming at me." Van Damme then assured Putin's bodyguards he was not reaching for any weapons!

▲

The French actor is known for being close to Vladimir Putin. So much so that he moved to Russia and was given Russian citizenship.

▲

"I love your president, Vladimir Putin, very much and it's mutual," Depardieu wrote in a letter to the Russian state television.

▲

Pamela Anderson is a known animal rights advocate. Vladimir Putin invited the actress to come to Russia after she wrote to him in 2015 asking for a ban on the the import of seal products.

▲

In 2018, Putin dully complied with Pamela Anderson's request and outlawed imported seal meat in the country.

▲

The then Russian prime minister met the supermodel at the International Tiger Conservation Forum on November, 23, 2010 in Saint Petersburg.

▲

Putin is pictured with the famous Spanish opera singer and the Russian conductor at the opening of the new Mariinsky II Theatre on May 2, 2013 in Saint Petersburg.

▲

The Russian ice hockey star has had a brilliant career in the NHL, so it doesn't really come as a surprise that he met the president.

▲

Ovechkin openly supported Putin during his 2017 campaign. "Being part of this team makes me proud," Ovechkin wrote. "I'm confident that there's a lot of us who support Vladimir Putin ... So let's come together and show everyone a strong and unified Russia!"

▲

While this gallery doesn't include all world leaders who met the Russian president, Trump, for better or worse, is a celebrity. The two first met back in 2013.

▲

While Trump had supported the annexation of Crimea in 2014, saying "The people of Crimea, from what I've heard, would rather be with Russia than where they were," he has condemned the more recent invasion of Ukraine.

Sources: (Grunge) (The Guardian) (BBC)