“River’s Edge” – 1986

Did you know Keanu was born in Beirut? Eventually, his mother became a costume designer and moved the family to places like Sydney, New York City and Toronto. As a teenager, he got work as a production assistant in movies before dropping out of school and moving to Los Angeles.

Keanu made his screen debut in an episode of Hangin’ In, and before long, he got a great part in the 1986 drama film River’s Edge. Here’s what he looked like then.

“Bill and Ted’s Excellent Adventure” – 1989

Keanu appeared in several other movies in the ’80s, but it was his role in Bill and Ted’s Excellent Adventure in 1989 that really made an impression.

“Bill and Ted’s Bogus Journey” – 1991

The actor was also in the 1991 sequel, Bill and Ted’s Bogus Journey. This is what he looked like at the premiere. Who knew that this guy would be John Wick one day?

“Point Break” – 1991

Keanu won MTV’s “Most Desirable Male” award in 1992 for his 1991 film Point Break. We can see why!

“The Matrix” – 1999

Keanu continued to evolve as an actor through the 1990s. In 1999, arguably one of his biggest roles of all time came out — The Matrix.

“The Matrix” (Again)

The science-fiction film was a huge hit and also starred big names like Laurence Fishburne and Carrie-Anne Moss.

Personal Tragedy – 2000

You wouldn’t necessarily know from the Keanu pictured here in 2000 what he was going through at the time. On December 24, 1999, his girlfriend, Jennifer Syme, gave birth eight months into her pregnancy to their daughter, Ava Archer Syme-Reeves, who was stillborn. They broke up, and in April 2001, Jennifer died in a tragic car accident.

“Matrix Reloaded “– 2003

Keanu was supposed to start shooting back-to-back Matrix sequels at the time — including The Matrix Reloaded, which Keanu attended the premiere of in this photo from 2003. Bret Domrose, who played guitar in the actor’s rock band Dogstar, said at the time that Keanu needed “peace and time” to deal with the sorrow in his life.

World Stunt Awards – 2004

Here, Keanu attended the annual World Stunt Awards at Paramount Studios in 2004. Thankfully, he seemed to bounce back from the tragedy in his life — or he at least knew how to hide his pain.

“Constantine” – 2005

Keanu starred in the horror-action film Constantine in 2005. It was yet another box office hit for the star.

“The Lake House” – 2006

Does anyone remember The Lake House movie from 2006? It was a nice, romantic film break from Keanu’s action and sci-fi projects. He starred in it with Sandra Bullock.

Director – 2009

In 2008, Keanu began pre-production on his directorial debut, Man of Tai Chi. It didn’t come out until 2013, but he starred in some movies that got less attention in the late 2000s as he worked. He’s pictured here in 2009.

Toyota Grand Prix – 2010

The Matrix actor participated in a Toyota Pro-Celebrity auto race event at the Toyota Grand Prix of Long Beach in Long Beach, California in 2010. Do you think he missed his calling to be a driver?

“Cloud Atlas” Premiere – 2012

He made an appearance at the Cloud Atlas film premiere in October 2012, possibly to support his Matrix film-making team, the Wachowskis.

“John Wick” – 2014

In October 2014, Keanu played the lead role in the action thriller John Wick. It received positive reviews and did well at the box office.

Film Independent Spirit Awards – 2014

But more importantly, John Wick helped remind the internet that Keanu is king.

“John Wick” Tokyo Premiere – 2015

The premiere events for John Wick are a gift to any Keanu fans, really. Here he is in Tokyo, Japan in September 2015, looking sharp in an all-black suit.

“John Wick: Chapter 2” Premiere – 2017

The first film did well enough that John Wick: Chapter 2 came out in 2017. He went to the Los Angeles premiere in January 2017.

“Always Be My Maybe” Premiere – May 2019

Check out how dapper the actor looked at the Always Be My Maybe premiere at the Village Theatre in Los Angeles in May 2019. This is the movie that reminded the world that Keanu is the ultimate Internet Boyfriend.

Oscars – February 2020

Keanu kept it classic in a black and white ensemble for the 2020 Oscars. More importantly, he brought his mom, Patricia Taylor, as his guest for the event!

Tell Us!

What’s your favorite Keanu look from his many years in show business? Do you have a favorite Keanu movie? Tell us in the comments below!