Career Timeline of Ryan Reynolds: Major Achievements and Milestones
From career breakthroughs to professional milestones, explore how Ryan Reynolds made an impact.
Ryan Reynolds is a highly successful Canadian-American actor, producer, and entrepreneur recognized for his roles in both comedic and superhero films. He has earned numerous accolades, including two Primetime Emmy Awards, and has been nominated for Grammy and Golden Globe Awards. Notably, he was the world's second-highest-paid actor in 2020 and 2024. Reynolds's films, in which he stars, have grossed over $6.6 billion globally, demonstrating his significant impact on the entertainment industry.
1966: Novel Published
In 1996, Ryan Reynolds portrayed Bobby Rupp in the miniseries In Cold Blood, an adaptation of Truman Capote's 1966 nonfiction novel of the same name.
1977: The Amityville Horror Novel
In 2005, Ryan Reynolds starred in The Amityville Horror which is an adaptation of the 1977 novel of the same name.
1979: The Amityville Horror Film Remake
In 2005, Ryan Reynolds starred in The Amityville Horror, a remake of the 1979 film of the same name.
1991: Began Career in Hillside
In 1991, Ryan Reynolds began his career in the Canadian teen soap opera Hillside, later distributed as Fifteen in the United States.
1993: Role in Hillside
In 1993, Ryan Reynolds continued his lead role in the teen soap opera Hillside, which began in 1991 and ended in 1993.
1993: Feature Film Debut in Ordinary Magic
In 1993, Ryan Reynolds made his feature film debut in the coming-of-age drama Ordinary Magic, playing Jeffrey.
1994: Dual Roles in The Odyssey
Between 1993 and 1994, Ryan Reynolds took on the dual roles of Macro and Lee in the children's television series The Odyssey, continuing from 1993.
1995: First The Outer Limits appearance
In 1995, Ryan Reynolds made his first appearance in The Outer Limits in "If These Walls Could Talk".
1996: TV Cameos and Sabrina the Teenage Witch
In 1996, Ryan Reynolds made cameo appearances in The X-Files and The John Larroquette Show, and co-starred in the television film Sabrina the Teenage Witch as Seth.
1997: Film with The Alarmist and The Outer Limits
In 1997, Ryan Reynolds returned to feature films with the dark comedy The Alarmist and appeared again in The Outer Limits.
1998: The Outer Limits
In 1998, Ryan Reynolds appeared again in The Outer Limits, playing the character Paul Nodel.
1998: Breakthrough Role in Two Guys and a Girl
In 1998, Ryan Reynolds had his breakthrough role as Michael "Berg" Bergen in Two Guys and a Girl.
1999: Minor Roles in Coming Soon and Dick
In 1999, Ryan Reynolds took on the minor roles of Henry Lipschitz and Chip in the comedies Coming Soon and Dick, respectively.
2000: Starred in Boltneck
In 2000, Ryan Reynolds starred as Karl in the horror comedy Boltneck.
2001: Two Guys and a Girl
In 2001, Ryan Reynolds continued his lead role in the sitcom Two Guys and a Girl. The show started in 1998 and ended in 2001.
2001: Finder's Fee
In 2001, Ryan Reynolds portrayed Quigley in the drama thriller Finder's Fee.
2002: Starred in National Lampoon's Van Wilder
In 2002, Ryan Reynolds played the titular character in the romantic comedy National Lampoon's Van Wilder, which was critically panned but achieved box office success.
2003: Starred in The In-Laws and Foolproof
In 2003, Ryan Reynolds portrayed Mark Tobias in The In-Laws and starred alongside Kristin Booth in Foolproof.
2004: Harold & Kumar Go to White Castle
According to Rotten Tomatoes, in 2004 one of Ryan Reynolds's most acclaimed films was Harold & Kumar Go to White Castle.
2004: Harold & Kumar and Blade Trinity
In 2004, Ryan Reynolds had a cameo in Harold & Kumar Go to White Castle, made his voice acting debut in Zeroman, and played Hannibal King in Blade: Trinity.
2004: Starred in Blade: Trinity
In 2004, Ryan Reynolds starred in the critically unsuccessful superhero film Blade: Trinity.
2005: Expressed Interest in Deadpool Adaptation
As early as 2005, Ryan Reynolds expressed interest in a potential Deadpool film adaptation.
2005: The Amityville Horror, Waiting... and Just Friends
In 2005, Ryan Reynolds starred in The Amityville Horror as George Lutz, Waiting... as Monty, and Just Friends as Chris Brander.
2005: Starred in Waiting...
In 2005, Ryan Reynolds starred in the romantic comedy Waiting...
2006: Starred in Smokin' Aces
In 2006, Ryan Reynolds played FBI agent Richard Messner in the crime action film Smokin' Aces.
2007: Starred in The Nines
In 2007, Ryan Reynolds played three distinct characters in the science fiction film The Nines.
2008: Roles in Chaos Theory, Definitely, Maybe, and Fireflies in the Garden
In 2008, Ryan Reynolds played Frank Allen in Chaos Theory, Will Hayes in Definitely, Maybe, and a novelist in Fireflies in the Garden.
2008: Runs New York City Marathon
In 2008, Ryan Reynolds ran the New York City Marathon for Team Fox.
2009: Adventureland
According to Rotten Tomatoes, in 2009 one of Ryan Reynolds's most acclaimed films was Adventureland.
2009: Joins Michael J. Fox Foundation Board
In 2009, Ryan Reynolds joined the board of the Michael J. Fox Foundation.
2009: Plays Wade Wilson / Weapon XI in X-Men Origins: Wolverine
In 2009, Ryan Reynolds played Wade Wilson / Weapon XI in X-Men Origins: Wolverine.
2009: Adventureland, X-Men Origins: Wolverine, The Proposal and Paper Man
In 2009, Ryan Reynolds starred in Adventureland as Mike Connell, X-Men Origins: Wolverine as Wade Wilson / Deadpool / Weapon XI, The Proposal as Andrew Paxton, and Paper Man as Captain Excellent.
2009: Starred in The Proposal and X-Men Origins: Wolverine
In 2009, Ryan Reynolds starred in the commercially successful romantic comedy The Proposal and the critically unsuccessful superhero film X-Men Origins: Wolverine.
2010: Buried
According to Rotten Tomatoes, in 2010 one of Ryan Reynolds's most acclaimed films was Buried.
2010: Sesame Street Guest Appearance and Buried
In 2010, Ryan Reynolds made a guest appearance on Sesame Street and starred in the survival thriller film Buried as Paul Conroy.
2011: The Whale
According to Rotten Tomatoes, in 2011 one of Ryan Reynolds's most acclaimed films was The Whale.
2011: Green Lantern and The Change-Up
In 2011, Ryan Reynolds played the titular character in Green Lantern and Mitch Planko in The Change-Up.
2011: Starred in Green Lantern
In 2011, Ryan Reynolds starred in the critically unsuccessful superhero film Green Lantern.
2012: Stars in Safe House and Cameo in Ted
In 2012, Ryan Reynolds starred in the action thriller "Safe House" alongside Denzel Washington, playing CIA agent Matt Weston. His safe house is breached, forcing them to escape. He also made a cameo appearance as Jared in the comedy "Ted".
2013: Voiced Turbo and The Croods
In 2013, Ryan Reynolds lent his voice to animated films including Turbo and The Croods franchise.
2013: Stars in R.I.P.D.
In 2013, Ryan Reynolds played Nick Walker in "R.I.P.D.", a detective murdered by his partner. The film was a box-office bomb and was panned by critics.
2013: Voice roles in The Croods and Turbo
In 2013, Ryan Reynolds voiced Guy in "The Croods", an inventive teenage caveboy, and the titular protagonist in "Turbo", a garden snail with superspeed who dreams of racing in the Indianapolis 500 and 24 Hours of Le Mans.
2014: Hollywood's most popular actor
In 2014, Richard Newby of The Hollywood Reporter called Ryan Reynolds "one of Hollywood's most popular actors for nearly 20 years", acknowledging his diverse range of roles, primarily in comedy, action, and superhero films.
2014: Acts in The Voices and The Captive
In 2014, Ryan Reynolds played Jerry Hickfang in the horror comedy "The Voices", voicing his pet dog and cat. He also portrayed Matthew in the psychological thriller "The Captive", a father searching for his missing daughter.
2015: Mississippi Grind
According to Rotten Tomatoes, in 2015 one of Ryan Reynolds's most acclaimed films was Mississippi Grind.
2015: Stars in Mississippi Grind, Woman in Gold and Self/less
In 2015, Ryan Reynolds starred as Curtis in "Mississippi Grind", played E. Randol Schoenberg in "Woman in Gold", and appeared in "Self/less".
2015: Starred in Woman in Gold
In 2015, Ryan Reynolds starred in the biographical drama Woman in Gold.
December 15, 2016: Star on the Hollywood Walk of Fame
On December 15, 2016, Ryan Reynolds received a star on the Hollywood Walk of Fame at 6801 Hollywood Boulevard.
2016: Deadpool
According to Rotten Tomatoes, in 2016 one of Ryan Reynolds's most acclaimed films was Deadpool.
2016: Stars in Criminal
In 2016, Ryan Reynolds played Bill Pope in the action thriller "Criminal".
2016: Golden Globe Nomination
In 2016, Ryan Reynolds received a Golden Globe nomination for Best Actor in a Motion Picture – Musical or Comedy for his role in Deadpool.
June 2017: Filming for Deadpool 2 Started
In June 2017, filming for the sequel to Deadpool started.
2017: Appeared in Life
In 2017, Ryan Reynolds appeared in the sci-fi horror film Life.
2017: The Hitman's Bodyguard
In 2017, Ryan Reynolds starred in "The Hitman's Bodyguard" which led to the sequel Hitman's Wife's Bodyguard in 2020.
2017: Stars in Life and The Hitman's Bodyguard
In 2017, Ryan Reynolds starred in the science fiction film "Life" and the action comedy "The Hitman's Bodyguard".
January 2018: Launches Maximum Effort
In January 2018, Ryan Reynolds launched the production company Maximum Effort and signed a deal with Fox. Also in January 2018, it was announced that a live-action adaptation of the board game Clue was in development.
February 2018: Acquires stake in Aviation American Gin
In February 2018, Ryan Reynolds acquired a stake in Aviation American Gin, overseeing the brand's creative direction.
2018: Deadpool 2
According to Rotten Tomatoes, in 2018 one of Ryan Reynolds's most acclaimed films was Deadpool 2.
2018: Grammy Nomination
In 2018, Ryan Reynolds received a Grammy nomination for Best Compilation Soundtrack for Visual Media for the soundtrack of Deadpool 2.
November 2019: Purchases stake in Mint Mobile
In November 2019, Ryan Reynolds purchased an ownership stake in Mint Mobile.
2019: Starred in 6 Underground and Detective Pikachu
In 2019, Ryan Reynolds appeared in action films like 6 Underground and lent his voice to the animated character Pikachu in Detective Pikachu.
2019: Stars in Detective Pikachu and 6 Underground
In 2019, Ryan Reynolds voiced the titular character in "Detective Pikachu", and starred in Michael Bay's "6 Underground".
May 2020: Reads James and the Giant Peach
In May 2020, Ryan Reynolds joined celebrities in reading "James and the Giant Peach" by Roald Dahl to support Partners In Health.
July 2020: Offers Reward for Stolen Teddy Bear
In July 2020, Ryan Reynolds and George Stroumboulopoulos offered $5,000 for the return of a stolen teddy bear belonging to a Vancouver woman.
September 2020: Talks to purchase Welsh football club Wrexham
In September 2020, Ryan Reynolds and Rob McElhenney were in talks to purchase the Welsh football club Wrexham.
November 2020: Takeover of Wrexham confirmed
In November 2020, Ryan Reynolds and Rob McElhenney's takeover of Wrexham was confirmed.
2020: The Croods: A New Age
According to Rotten Tomatoes, in 2020 one of Ryan Reynolds's most acclaimed films was The Croods: A New Age.
2020: Voted for the first time
Around 2018, Ryan Reynolds attained American citizenship, and in 2020, he voted for the first time in the presidential election.
2020: Celebrity 100 list
In 2020, Ryan Reynolds appeared in the Celebrity 100 list, a compilation of the 100 most powerful public figures in the world, as selected by Forbes. He was also listed as the second-highest-paid actor in the world, with earnings of $71.5 million.
2020: Continued Voicing The Croods
In 2020, Ryan Reynolds continued lending his voice to The Croods franchise of animated films.
2020: Joins Match Group Board and Sells Aviation American Gin
In 2020, Ryan Reynolds joined the board of Match Group and sold Aviation American Gin to Diageo.
2020: The Croods: A New Age and Hitman's Wife's Bodyguard
In 2020, Ryan Reynolds reprised his role as Guy in "The Croods: A New Age" and Michael Bryce in "Hitman's Wife's Bodyguard".
2020: Second Highest-Paid Actor
In 2020, Ryan Reynolds was the world's second-highest-paid actor. He is known for starring in comedic and superhero films.
February 2021: Approval from the Financial Conduct Authority
In February 2021, Ryan Reynolds and Rob McElhenney received approval from the Financial Conduct Authority for their takeover of Wrexham.
June 23, 2021: Maximum Effort's marketing division acquired by MNTN Software
On June 23, 2021, Maximum Effort's marketing division was spun off and acquired by MNTN Software.
October 2021: Sabbatical Announcement
In October 2021, Ryan Reynolds announced he was taking a sabbatical after the production of "Spirited".
November 26, 2021: Governor General Performing Arts Award
On November 26, 2021, Mary Simon, governor general of Canada, honoured Ryan Reynolds with a Governor General Performing Arts Award.
2021: Free Guy
According to Rotten Tomatoes, in 2021 one of Ryan Reynolds's most acclaimed films was Free Guy.
2021: Free Guy and Red Notice Release
In 2021, Ryan Reynolds starred in "Free Guy" and "Red Notice".
March 2022: Donation to Water First
In March 2022, Ryan Reynolds and Blake Lively donated $500,000 to Water First, providing clean water to Indigenous communities in Canada.
October 2022: Humanitarian Award
In October 2022, Ryan Reynolds was honoured with the Academy of Canadian Cinema and Television's Humanitarian Award.
2022: Pledge to support Ukrainian refugees
Following the 2022 Russian invasion of Ukraine, Ryan Reynolds and Blake Lively pledged to match donations up to $1 million for Ukrainian refugees.
2022: Starred in The Adam Project
In 2022, Ryan Reynolds appeared in the action film The Adam Project.
2022: Investment in several companies
In 2022, Ryan Reynolds invested in Wealthsimple, 1Password and FuboTV.
2022: The Adam Project and Spirited
In 2022, Ryan Reynolds starred in "The Adam Project" and "Spirited".
2022: Welcome to Wrexham Released
In 2022, Welcome to Wrexham, a television series documenting Ryan Reynolds's co-ownership of Welsh soccer club Wrexham, premiered.
March 2023: T-Mobile Acquires Mint Mobile
In March 2023, T-Mobile announced its acquisition of Mint Mobile.
April 2023: Invests in Nuvei
In April 2023, Ryan Reynolds invested in Canadian payments technology company Nuvei.
August 2023: Donation to SAG-AFTRA Foundation
In August 2023, Ryan Reynolds and Blake Lively donated $1 million to the SAG-AFTRA Foundation's financial assistance program.
August 2023: Order of British Columbia
In August 2023, Ryan Reynolds was announced as a recipient of the Order of British Columbia, British Columbia's highest honour.
October 2023: Donation to the International Committee of the Red Cross
In October 2023, Ryan Reynolds and Blake Lively donated $1 million to the International Committee of the Red Cross to support children affected by the conflict between Israel and Gaza.
November 2023: Order of British Columbia Ceremony
In November 2023, Ryan Reynolds and his fellow honourees were scheduled to receive the Order of British Columbia at a ceremony in Victoria.
August 2024: Box Office Success
In August 2024, Ryan Reynolds and Blake Lively had separate films, "Deadpool & Wolverine" and "It Ends with Us" respectively, leading at the box office.
August 2024: Contribution to "It Ends With Us"
In August 2024, during a red carpet interview, Blake Lively revealed that Ryan Reynolds contributed dialogue to a rooftop scene in the 2024 film, "It Ends with Us".
October 2024: Donation to Feeding America
In October 2024, Ryan Reynolds and Blake Lively donated $1 million to Feeding America to aid relief efforts in Florida affected by hurricanes.
December 19, 2024: Officer of the Order of Canada
On December 19, 2024, Ryan Reynolds was appointed an Officer of the Order of Canada, recognizing both his achievements in film and his philanthropic contributions.
2024: Deadpool & Wolverine
According to Rotten Tomatoes, in 2024 one of Ryan Reynolds's most acclaimed films was Deadpool & Wolverine.
2024: Second-highest-paid actor in the world
In 2024, Forbes listed Ryan Reynolds as the second-highest-paid actor in the world for a second time, with earnings of $85 million. He was also included on Harper's Bazaar's list of the 50 Hottest Men of All Time.
2024: Grammy Nomination
In 2024, Ryan Reynolds was nominated again for the soundtrack of Deadpool & Wolverine.
2024: Second Highest-Paid Actor
In 2024, Ryan Reynolds was the world's second-highest-paid actor. He is known for starring in comedic and superhero films.
September 2025: Film Grosses
As of September 2025, Ryan Reynolds's films have grossed over $6.6 billion worldwide.
2050: The Adam Project
In 2050, Adam Reed travels back in time in "The Adam Project" released in 2022.
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