1990

Canadian Beginnings

Reynolds makes his Canadian TV debut in the Nickelodeon series Hillside, known as Fifteen in the U.S. He earns a Young Artist Award nomination in 1993. The actor, who later calls the series "absolutely abominable," says, "I think stoned college kids kept it on the air for three years…People watched it because it was so bad."

1998

Ryan Reynolds

March 11

American TV

After a slew of appearances and guest stints, including Sabrina the Teenage Witch and The X-Files, Reynolds stars as fun-loving med student Berg in Two Guys, a Girl, and a Pizza Place. During its tumultuous run, Reynolds defends the show, saying, "If you can get big numbers, that's great, but ultimately the only goal is to be proud of each week's show. And I think we are here." It's cancelled in 2001.

2002

Ryan Reynolds

April 05

Breakout Star

Playing seventh-year college student-turned-party planner Van Wilder, Reynolds makes his comedic breakthrough. Though Van Wilder only grosses $21.3 million, it becomes a cult classic. The film's popularity even leads Waiting costar Justin Long to later refer to Reynolds as "the frat guys' Jesus Christ."

2004

Ryan Reynolds

June 16

Canada's First Couple

After two years of dating, Reynolds and musician girlfriend Alanis Morissette get engaged. The two began dating after meeting at Drew Barrymore's 2002 birthday party. "We have the perfect combination of compatibility and incompatibility that makes the relationship very passionate," Morrissette tells PEOPLE. "It's perfect."

Ryan Reynolds

December 08

Ryan Gets Ripped!

For his role as a vampire hunter in Blade: Trinity, opposite Jessica Biel and Wesley Snipes, Reynolds sheds his frat boy persona and debuts a super-buff bod. To prepare for the role, Reynolds reduces his body fat to just 3 percent and takes martial arts classes. Of the classes, Reynolds tells PEOPLE, "I don't think that it worked very well because I got the crap kicked out of me repeatedly."

2005

Ryan Reynolds

April 15

Amityville Tops Box Office

The Amityville Horror opens at No. 1, pulling in $23.5 million at the box office. In the remake of the 1979 film, Reynolds stars as the possessed George Lutz, a father and husband who mentally unravels during his family's 28 days in a haunted home. "It was exciting for me," Reynolds tells PEOPLE. "I liked the thought of this guy being a bear, a big intimidating presence." That November, the actor returns to comedy with Just Friends, in which he sports a 60 lb. fat suit.

2007

Ryan Reynolds

February 02

Moving On From Alanis

Following a brief split, on-again, off-again couple Reynolds and Morissette end their engagement. As recently as April, the 30-year-old actor is spotted with Scarlett Johansson, 22. They get engaged the following year.

2008

Ryan Reynolds

February 14

Playing Abigail's Daddy

Reynolds stars in his first adult romantic comedy, Definitely, Maybe, as a divorced dad explaining to daughter Abigail Breslin how he met her mother. "I was looking for a Tom Hanks, Jimmy Stewart kind of quality," says Definitely writer-director Adam Brooks, "and I felt that Ryan just wasn't this Van Wilder guy, that there was this natural, relaxed actor in him."

Ryan Reynolds

September 27

Scarlett & Ryan Wed

Johansson, 23, takes one of PEOPLE's 'sexiest men' off the market, when Reynolds, 31, marries Johansson in an intimate ceremony on Vancouver Island. "Scarlett wanted a ceremony with just family and a few select friends," a source close to the bride tells PEOPLE. Less than 40 people attend the wedding, which found the groom fishing while other guests went horseback riding and mountain biking.

2009

Ryan Reynolds

May 01

Following in Hugh's Claws

After X-Men Origins: Wolverine rakes in $87 million opening weekend, 20th Century Fox and Marvel Comic green light a spin-off featuring Reynolds' character Deadpool. A fan of the wise-cracking mercenary formerly known as Wade Wilson, Reynolds tells MTV, "To stay as true to the source material as possible is the only way to do it, and I say that because there's nothing more interesting than the source material for Deadpool."

Photo Credits

BIOGRAPHY (top to bottom): Everett Collection; everett collection; Eric Charbonneau/BEImages; New Line; MGM; Flynet; Universal Studios; JLM / Splash News Online; Everett

Edited by Julia Wang

Ryan Reynolds

Celebrity Central / Top 25 Celebs

 

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