1991: Reynolds' career began with 'Hillside,' a Nickelodeon teen soap that aired in the States as 'Fifteen.' Consider it an angsty precursor to 'Degrassi.'
1996: Those currently watching the miniseries reboot of 'The X-Files' might want to find the wacky third-season episode "Syzygy," which opens with Reynolds playing a poor sap who gets hanged off the edge of a cliff by two murderous teen girls.
1996: If you're looking for the birth of Reynolds' heartthrob image, look no further than the TV film pilot for 'Sabrina The Teenage Witch.' Reynolds plays Sabrina's hunky crush Seth, who sports a winning smile and a quintessentially ridiculous '90s haircut.
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1998: Reynolds' first lead role came in the ABC sitcom 'Two Guys, a Girl and a Pizza Place,' in which he played Michael "Berg" Bergen, a sort-of dopey grad student who works at a pizza joint while figuring out what he wants to do with his life.
2002: Reynolds' deftness as an aimless twentysomething earned him his first movie lead in "National Lampoon's Van Wilder," in which he played the titular party boy slacker who is challenged to finally graduate from college and get on with his life.
2003: Reynolds attended the MTV Movie Awards with Alanis Morissette. The couple announce their engagement the following year, before splitting in 2007. Morissette said her album "Flavors of Entanglement" was inspired by the breakup.
2004: Reynolds shifted gears and made his first steps towards becoming a comic book/action film star in "Blade: Trinity." His performance as vampire hunter Hannibal King required dozens of hours of intense physical training.
2005: Reynolds bolstered his rep as a beefcake star with his often-shirtless appearance in the remake of "The Amityville Horror."
Smokin' Aces" was the first film in which Reynolds got a chance to perform alongside a top name in Hollywood. Here, he works with Ray Liotta
as a pair of FBI agents assigned to protect a Vegas gangster who has made an immunity deal with the feds and is now being hunted by multiple assassins.
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2009: Reynolds made his first go-around as Deadpool in "X-Men Origins: Wolverine," but the timeline retooling in "Days of Future Past" means that Reynolds' return to the role will give Deadpool a clean slate.
20th Century Fox
2009: Reynolds as the quick-witted mercenary Wade Wilson before he transforms into Deadpool in "X-Men Origins: Wolverine."
2009: Reynolds cemented his rep as a hunk with this revealing Entertainment Weekly cover.
Teaming with Sandra Bullock
on the romantic comedy "The Proposal," Reynolds scored one of his biggest hits ($164 million domestically). And sets heart aflutter with this shirtless scene.
Reynolds attended the Tony Awards with his then wife, Scarlett Johansson
, who won an award for her Broadway debut in "A View From the Bridge." The actor filed for divorce that December after just over two years of marriage.
2010: Reynolds received high praise from critics at Sundance and a Goya Award nomination for his work as a hostage buried alive in the terrifying thriller "Buried."
2010: Reynolds was named People's Sexiest Man Alive, and told the magazine he prefers to sleep in the nude "because if anyone breaks into your house, I can't think of anything more frightening than a naked 6'2" man coming at you."
2011: Reynolds got the chance to take center stage in a comic book film as Hal Jordan in "Green Lantern."
2011: But the DC Comics film was critically panned and largely ignored at the box office. Needless to say, no "Green Lantern" sequel is imminent.
Over the next three years, Reynolds starred alongside several Oscar winners, starting with Denzel Washington
in "Safe House." Reynolds played a CIA agent assigned to guard an alleged turncoat played by Washington as the duo are hunted through the streets of Cape Town.
: Reynold married his "Green Lantern" co-star Blake Lively
in an intimate ceremony at Boone Hall Planation in Mount Pleasant, S.C., on Sept. 9.
The next dance with a top star wasn't as well received. In "R.I.P.D.," Reynolds starred alongside Jeff Bridges
as one of a pair of deceased lawmen who operate from the afterlife to stop the undead from attacking the living. The film was slammed as a hybrid rip-off of 'Ghostbusters' and 'Men in Black.'
BBC Films/The Weinstein Company
Reynolds received a better reception when he starred alongside Helen Mirren
in the prestige flick "Woman in Gold." Reynolds played a fledgling lawyer called upon by an elderly Jewish refugee played by Mirren to help recover a family painting long ago stolen by the Nazis.
20th Century Fox
2016: And now Reynolds gets to play Deadpool in all his irreverent, smart-alecky glory. Prepare for infinite winks to the audience and a send-up of the superhero movie formula.
Reynolds, whose wife, Blake Lively
, gave birth do a daughter named James in December 2014, was named People magazine's "Sexiest Dad Alive."
2017: Reynolds swapped roles with Jake Gyllenhaal in the sci-fi thriller "Life" about astronauts who discover not-so-friendly living beings on Mars.