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1986: A Young Man

Keanu Reeves was born in Beirut, Lebanon, but he moved frequently and bounced around from Hawaii to Australia to New York to Canada. At 15, Reeves decided he wanted to be an actor and pursued the career while attending Avondale Secondary Alternative School in Canada.

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1986: His Big Break

Although it wasn't his first starring role, Reeves earned his breakout role in the 1987 crime drama River's Edge. Reeves starred alongside up-and-coming British actress Ione Skye.

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1987: A Rising Star

Reeves worked on several movies in the late '80s after his big break in River's Edge, including Dangerous Liaisons, which showcased his range as an actor.

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1987: The Beginning of an Excellent Adventure

One of Reeve's earliest roles was in the slapstick comedy Bill and Ted's Excellent Adventures. Reeves, pictured here on set in 1987, played the dumb, goofy Ted Theodore Logan, who accidentally accesses a time machine with his buddy Bill.

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1988: Hanging Around

A young Reeves is seen relaxing on set in 1988.

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1988: Bonafide Celebrity

Reeves and "Brat Pack" member, Rob Lowe, were teammates in a celebrity basketball tournament in 1988. By this time, Reeves had become known as a promising rising star in Hollywood.

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1989: Mysterious Romance

Rumors about Reeves and his Bram Stoker's Dracula costar, Winona Ryder, circulated for years. Many were convinced that their chemistry was so good, they must have been an item in the past. Ryder tried to shut down the rumors in 2018, but gassed them up instead: "We actually got married in Dracula. No, I swear to god I think we're married in real life," the actress told Entertainment Weekly.

The pair explained that their director, Frances Ford Coppola, used a real Romanian priest to act in the wedding scene and that their vows may have actually been legit.

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1990: Reeves Forms Dogstar

Reeves quickly became known for one of his outside of acting hobbies, his grunge band Dogstar. As lead guitarist, Reeves and his band had performances at some of the most popular clubs in Los Angeles, like the Troubadour.

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1991: The Adventure Continues

Reeves and his costar, Alex Winter, attend the premiere of Bill & Ted's Excellent Adventure. The movie, which remains a fan favorite to this day, was turned into a cartoon TV show and had a sequel, Bill & Ted's Bogus Journey.

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1991: Filming 'Point Break'

In one of his most famous films, Point Break, Reeves costarred alongside Patrick Swayze as a surfer.

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1991: 'Point Break' Premiere

Reeves channeled his chill and laid-back surfer vibes for his appearance at the Point Break premiere.

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1992: A New Look

The actor looks poised and polished as he debuted a new shorter haircut at the MTV Movie Awards. Was this the end of his grunge phase? Nah, it was just another sign of his endless versatility.

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1992: A Young Hollywood Romance

After meeting on the set of Bram Stoker's Dracula, Reeves and Sofia Coppola (who's father directed the film) dated on and off following the film's release.

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1993: Little Buddha

In 1993, Reeves (far right) donned a wig to play Siddhartha in the critically acclaimed film, Little Buddha.

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1993: Direction on Set

Italian director and scriptwriter Bernardo Bertolucci gives Reeves notes while on the set of Little Buddha.

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1993: A Big Mistake

Reeves was well known for pulling up to premieres and events on one of his multiple motorcycles, but in 1993 it was his car that found him at the end of a costly mistake. The actor was arrested in Los Angeles for drunk driving after being pulled over for erratic driving.

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1993: A Shakespearian Role

In 1993, the actor joined a star studded cast—Emma Thompson, Denzel Washington, and Kenneth Branagh—in the highly-anticipated film adaption of William Shakespeare's Much Ado About Nothing.

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1994: Cementing His Fame

In 1994, Reeves' career reached new heights due to his role in the blockbuster hit, Speed. Reeves and his costar, Sandra Bullock, are seen here imprinting their hands and signatures on slabs of cement for Planet Hollywood.

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1994: Dogstar Makes It Big

While blowing up on the screen, Reeves's band, Dogstar, also had a banner year in 1994. They landed a spot in the lineup at Glastonbury Festival.

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1994: Just Friends

They've remained famous friends since meeting on the set of Speed, but rumors flew about a romantic connection between the two back in the day. Both stars have revealed, separately we may add, that they had a crush on the other while filming.

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