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“Hillside” (1991) 

Reynolds’ career began with “Hillside,” a Canadian-American teen soap from Nickelodeon that aired in the States as “Fifteen.” Consider it an angsty alternative to “Degrassi.”

YTV

“The X-Files” (1996)

In an episode during the third season of “The X-Files” titled “Syzygy,” Reynolds can be seen playing a poor sap who gets hanged off the edge of a cliff by two murderous teen girls.

Fox

“Sabrina the Teenage Witch” (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.

Showtime

“Two Guys, a Girl and a Pizza Place” (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.

20th Century Fox

“National Lampoon’s Van Wilder” (2002)

Reynolds’ deftness as an aimless 20-something 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.

Lionsgate

2003 

Reynolds attended the MTV Movie Awards with Alanis Morissette. The couple announced their engagement the following year, before splitting in 2007. Morissette said her album “Flavors of Entanglement” was inspired by the breakup.

Getty Images

“Blade: Trinity” (2004)

Reynolds shifted gears and made his first steps toward 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.

New Line

“The Amityville Horror” (2005)

Reynolds bolstered his rep as a beefcake star with his often-shirtless appearance in the remake of “The Amityville Horror.”

MGM

“Smokin’ Aces” (2006)

“Smokin’ Aces” was the first film in which Reynolds got a chance to perform alongside a top name in Hollywood. Here, he and Ray Liotta play 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.

Universal

“X-Men Origins: Wolverine” (2009)

Reynolds made his first go-around as Deadpool in “X-Men Origins: Wolverine.” It’s a slightly different take on the Deadpool character we’ve come to love, with Reynolds playing Wade Wilson as a quick-witted mercenary before transforming into the all-powerful, evil and mute Deadpool. Thankfully he got the chance to do a more playful reboot of the character. 

20th Century Fox

“The Proposal” (2009)

That same year, it looked like Reynolds’ career was heading in a different direction from superheroes when he starred in “Adventureland” and teamed with Sandra Bullock on the romantic comedy “The Proposal.” The latter was one of Reynolds’ biggest hits, earning $164 million domestically.

Touchstone Pictures

2010

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.

Getty Images

“Buried” (2010)

Some of the biggest critical acclaim of Reynolds’ career came when he starred in the claustrophobic thriller “Buried,” spending the whole movie trapped underground as a hostage buried alive. The movie played at Sundance and won Reynolds a Goya Award nomination.

Lionsgate

2010

Quickly on the rise as a star, Reynolds was named People’s Sexiest Man Alive, and he 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.”

“The Green Lantern” (2011)

In what was meant to cement Reynolds as an A-list star, Reynolds starred as Hal Jordan in DC Comics’ tentpole film “The Green Lantern.” But the superhero movie was critically panned and a box office disappointment, setting Reynolds back a few years. Needless to say, no “Green Lantern” sequel is imminent. 

Warner Bros.

“Safe House” (2012)

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.

Universal

2012

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.

Getty Images

“R.I.P.D.” (2013)

Reynolds’ 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.”

Universal

“Woman in Gold” (2015)

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.

BBC Films/The Weinstein Company

“Deadpool” (2016)

Reynolds finally found his signature role when he played the irreverent, smart-alecky “Merc with a Mouth” Deadpool. The R-rated superhero comedy held nothing back in its knowing winks to the audience, along with its bloody, profane style and action scenes. The film made $783.1 million worldwide. 

20th Century Fox

“Deadpool 2” (2018)

By the time the second “Deadpool” came out, Reynolds had wholeheartedly embraced the character and leaned into every aspect of the film’s marketing. He made hilarious and subversive videos with Celine Dion, riffed on Bob Ross and “The Princess Bride” and even took over Stephen Colbert’s monologue. The second film was an equally impressive smash, earning $785 million worldwide. 

Sony

“Feud” with Hugh Jackman (2018)

Reynolds and Wolverine himself, Hugh Jackman, carried on an extended fake feud as the best of “frenemies” throughout 2018, trading barbs and fake political smear ads on social media, all culminating in Jackman and Reynolds exchanging commercials for each other’s brands.

Getty Images

“Pokemon: Detective Pikachu” (2019)

In a promotional short for “Detective Pikachu,” Blake Lively ribbed Reynolds for not even attempting to change his voice to portray the iconic Pokemon. But Reynolds’ charm along with the “Deadpool” style marketing proved to be the perfect fit for the family film. 

Warner Bros.