90s movie heartthrob hasn’t aged a day despite turning 50 today-Kitty Chrisp-Entertainment – Metro

Yes, this is Ryan Phillippe (Picture: Instagram/ryanphillippe)

Ryan Phillippe is celebrating his 50th birthday today – but he could genuinely pass as being 20 years younger.

The Cruel Intentions actor was a major 90s heartthrob and it seems nothing has changed as he glides into his fifth decade looking like a fresh-faced 30-something.

The actor rocketed into the mainstream as one of the hottest stars of the decade after his ground-breaking first role as Billy Douglas – the first openly gay teenager featured in a TV series – on US soap One Life to Live.

He gained popularity through appearances in Crimson Tide, 54, Little Blue Boy, White Squall, Nowhere, and of course Cruel Intentions.

While he boomed in the 1990s, Ryan was also known for going out with – and later marrying in 1999 – Reese Witherspoon.

It was widely believed the pair met on the set of Cruel Intentions, but in a 2019 interview Reese revealed they actually met at her 21st birthday party.

The 90s heartthrob hasn’t aged much since his hey-day (Picture: Moviestore/REX/Shutterstock)

The star is the father of Reese Witherspoon’s two children (Picture: Instagram/ryanphillippe)

Talking to Jane magazine, the Morning Show star said: ‘I don’t know what came over me – maybe the seven Midori sours – but I told him, “I think you’re my birthday present,”‘.

She added: ‘He thought it was so flattering and now that I think about it … how embarrassing!’

The pair welcomed two children together – Ava, 25, and Deacon, 20 – but Reese filed for divorce in 2006 citing ‘irreconcilable differences’ and Ryan was later accused of cheating, though neither ever spoke out about the reason behind their split.

However, it seems whatever happened they are on good terms as the pair sometimes reunite to celebrate their children’s big milestones.

He has more tattoos now, but doesn’t look 50 (Picture: Instagram/ryanphillippe)

He starred in Cruel Intentions alongside Reese, who he married in 1998 (Picture: Kerry Hayes/Miramax/Kobal/REX/Shutterstock)

This year also marked 25 years since Cruel Intentions hit the screens, and Ryan appeared alongside ex-wife Reese Witherspoon, Selma Blair and Sarah Michelle Gellar for the cult classic.

In the 1999 film, based on the 1782 novel Les Liaisons Dangereuses (Dangerous Liaisons), Ryan played a high school student called Sebastian Valmont who made a bet with his stepsister Kathryn Merteuil (Sarah Michelle Gellar) that he could seduce the new principal’s daughter Annette Hargrove (Reese Witherspoon).

At the same time, Kathryn tasks Sebastian with taking Cecile Caldwell’s (Selma Blair) virginity as revenge for her ex-boyfriend.

Despite its disturbing plot, Cruel Intentions raked in over $76million at the global box office and became a hit.

The pair later divorced, but still celebrate their children’s milestones together (Picture: Instagram/ryanphillippe)

They met at Reese’s 21st birthday party (Picture: Robin Platzer/Twin Images/Getty Images)

Marking the anniversary of Cruel Intentions in March, director Roger Kumble admitted to Metro.co.uk it would never be made in 2024.

‘No. I don’t think so,’ he replied, adding: ‘From the first opening thing where [Tara Reid’s character says] “There’s pictures of me on the internet”, someone said to me, “You kind of created revenge porn.” I was like, “Wow, thanks so much! Oh, great, my obit is written.”

‘We hit on some tropes that still exist today, that were still scandalous for its time and are still scandalous today.

‘It was risky, we really hit some taboos. [Sebastian] does some horrible things. But, because of Selma’s performance, and because of how she plays these scenes – in the hands of another actress, this movie would have gone off the rails.

‘She’s dressed as Little Red Riding Hood and the fact that what he’s doing is raping her. We end that scene on a comic pratfall out of frame, the tone of it… You could never pull that off today.

‘It’s its own little time capsule. The fact that it is set up earlier means that you’re laughing before then, so it’s not veering. That’s why the movie works in its own way right now.’

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