"Grief never ends." Within just 18 months, Keanu Reeves lost his baby and the love of his life.

There’s arguably no face in Hollywood who musters more 90s nostalgia than Keanu Reeves.

Reeves’ film repertoire, Hollywood social circle, and candid, often poetic, media presence encapsulates the angst of the era so pivotal to the pop culture world.

Not to mention his 90s pin-up looks – conventionally handsome, broody with a slight eccentric air.

But the now 54-year-old Matrix star's life away from the camera is one riddled with tragedy.

From an absent father to the loss of a child, best friend and great love - his story is one of  remarkable resilience in the face of heartache.

His childhood was nomadic - the Reeves family moved around. They spent time in Lebanon, Australia and the US, before settling in Toronto, Canada. By this stage in his childhood, his father had dropped out of picture, leaving his mother to take care of him and his younger sister Kim.

Reeves' father was later arrested for possession of heroin and cocaine, and sentenced to ten years in jail in 1994. He was released in 1996.

"The story with me and my dad’s pretty heavy. It’s full of pain and woe and f**king loss and all that shit," Reeves once told Rolling Stone.

His mother later became a costume designer in Hollywood, shortly before Reeves embarked on his own acting career - having left high school without receiving a diploma.

Keanu Reeves was thrust into the spotlight in 1986, starring in River's Edge, an indie crime film following the story of a murder within a group of Californian teenage burnouts.

Carrying his growing cult status through to the early 90s, he went on to star alongside fellow edgy teen heartthrob River Phoenix in Gus Van Sant's indie drama My Own Private Idaho.

The two actors became close, but then tragically, River Phoenix overdosed on a lethal concoction of cocaine, morphine, and Valium outside The Viper Room, an LA club owned by Johnny Depp. It was 1993 - Phoenix was just 23 years old.

It was, in a twisted irony, the year before Reeves' own father was caught - and subsequently arrested - with large amounts of heroin and cocaine.

During a Reddit "Ask Me Anything" in 2014, Reeves was asked about his dear friend.

“He was a remarkable human person and actor. We got along very well, and I miss him. I think of him often,” he replied.

Throughout his career, notoriously private Keanu Reeves has been linked to a number of famous women - Sandra Bullock, Sofia Coppola, Parker Posey and China Chow, to name a few.

But it was his relationship with Jennifer Syme that came to a tragic end.

In 1998, Reeves met the young actress, who at the time was working as filmmaker David Lynch's assistant, at a party thrown for his rock band Dog Star.

 

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They immediately began dating, and a year later were expecting a child together. In 1999, Syme gave birth to a stillborn daughter - only a month before baby Ava's due date.

In 2001, at 28 years old, Syme died in a car accident on the way to a party at Marilyn Manson's house.

Manson claimed in his memoir The Long Hard Road Out of Hell that he had sent Syme home from the party with a designated driver, but on arriving home, she decided to get in her own car and drive back.

In a 2006 interview with Parade magazine, Reeves said of Syme's death: "Grief changes shape, but it never ends. People have a misconception that you can deal with it and say, ‘It’s gone, and I’m better’. They’re wrong. When the people you love are gone, you’re alone."

"I miss being a part of their lives and them being part of mine. I wonder what the present would be like if they were here – what we might have done together. I miss all the great things that will never be," he added.

And the hardship continued for Reeves, when his sister Kim - also an actress - fell ill with leukemia in 1991 at the age of 25. After nearly a decade, Kim went into remission in 1999.

“When she was in the hospital he was there with her all the time, sitting at her bedside, holding her hand. Sometimes, it’s almost like he doesn’t trust himself to have a relationship with anyone,” a close friend of Reeves' once revealed to People.

He reportedly donated 70 per cent of his earnings from The Matrix to hospitals that treat leukemia, and often makes private donations to cancer research.

Amongst all this - Keanu Reeves had his own brush with death, falling off his motorbike in 1988, an accident which led to his damaged spleen being removed from his stomach.

"I remember saying in my head ‘I’m going to die,'" he told Rolling Stone.

Yet, the Speed actor remains one of the most down-to-earth celebrities of Hollywood, seeming to have avoided some of the pitfalls of fame.

How?

He once told fans in a Reddit AMA: "It’s easy to stay grounded. The ground is very close. And we walk on it every day."