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 Canadian-American actor, producer, and entrepreneur renowned for his comedic and superhero film roles. He achieved the distinction of being the world's second-highest-paid actor in both 2020 and 2024. His accolades include two Primetime Emmy Awards and nominations for two Grammy Awards and a Golden Globe Award. Films where Reynolds held a leading role have collectively grossed $6.6 billion globally, highlighting his significant impact on the entertainment industry.
1966: In Cold Blood Adaptation
In 1996, Reynolds portrayed Bobby Rupp in the two-part miniseries In Cold Blood (1996), an adaptation of Truman Capote's 1966 nonfiction novel of the same name.
1977: The Amityville Horror Novel
In 2005, Reynolds starred in The Amityville Horror, an adaptation of the 1977 novel of the same name.
1979: The Amityville Horror Film
In 2005, Reynolds starred in The Amityville Horror, an adaptation and remake of the 1979 film of the same name.
1991: Hillside Debut
In 1991, Ryan Reynolds began his career in the Canadian teen soap opera Hillside.
1993: Feature Film Debut
In 1993, Ryan Reynolds made his feature film debut in Ordinary Magic.
1994: The Odyssey Roles
Between 1993 and 1994, Ryan Reynolds played dual roles in the television series The Odyssey.
1995: Outer Limits Appearance
In 1995, Ryan Reynolds made his first appearance in The Outer Limits in the episode "If These Walls Could Talk".
1996: Television Appearances
In 1996, Ryan Reynolds made cameo appearances in The X-Files and The John Larroquette Show. He also co-starred in the TV film Sabrina the Teenage Witch.
1997: The Alarmist
In 1997, Ryan Reynolds returned to feature films with The Alarmist.
1998: 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 Comedy Roles
In 1999, Ryan Reynolds took on minor roles in the comedies Coming Soon and Dick.
2000: Deadpool film in development
As early as the year 2000, development began for the Deadpool movie that would later star Ryan Reynolds.
2000: Boltneck
In 2000, Ryan Reynolds starred in the horror comedy Boltneck as Karl.
2001: Finder's Fee Role
In 2001, Ryan Reynolds portrayed Quigley in the drama thriller Finder's Fee.
2002: National Lampoon's Van Wilder
In 2002, Ryan Reynolds played the titular character in the romantic comedy National Lampoon's Van Wilder.
2003: The In-Laws and Foolproof
In 2003, Ryan Reynolds portrayed Mark Tobias in The In-Laws and starred in Foolproof.
2004: Harold & Kumar Go to White Castle
According to Rotten Tomatoes, in 2004, 'Harold & Kumar Go to White Castle' was one of Ryan Reynolds's most acclaimed films.
2004: Harold & Kumar Cameo and Voice Acting Debut
In 2004, Ryan Reynolds had a cameo in Harold & Kumar Go to White Castle and made his voice acting debut in Zeroman. He also played Hannibal King in Blade: Trinity.
2005: Deadpool Interest
As early as 2005, Ryan Reynolds had expressed interest in a potential Deadpool film adaptation.
2005: Starring in Horror and Comedy Films
In 2005, Ryan Reynolds starred in The Amityville Horror, Waiting..., and Just Friends.
2006: Smokin' Aces
In 2006, Ryan Reynolds played FBI agent Richard Messner in the crime action film Smokin' Aces.
2007: The Nines
In 2007, Ryan Reynolds played three distinct characters in The Nines.
2008: Roles in Various Films
In 2008, Ryan Reynolds played Frank Allen in Chaos Theory, Will Hayes in Definitely, Maybe, and a novelist in Fireflies in the Garden.
2008: Ran New York City Marathon for Team Fox
In 2008, Ryan Reynolds ran the New York City Marathon for Team Fox to support the Michael J. Fox Foundation.
2009: Adventureland Acclaim
According to Rotten Tomatoes, in 2009, 'Adventureland' was one of Ryan Reynolds's most acclaimed films.
2009: Joined the board of the Michael J. Fox Foundation
In 2009, Ryan Reynolds joined the board of the Michael J. Fox Foundation, continuing to support research for a cure for Parkinson's disease.
2009: Portrayal of Wade Wilson / Weapon XI in X-Men Origins: Wolverine
In 2009, Ryan Reynolds portrayed Wade Wilson / Weapon XI in "X-Men Origins: Wolverine", leading to his heavy involvement in the development of the Deadpool film.
2009: Adventureland, X-Men Origins: Wolverine, The Proposal
In 2009, Ryan Reynolds starred in Adventureland, X-Men Origins: Wolverine as Deadpool, and The Proposal.
2010: Buried Acclaim
According to Rotten Tomatoes, in 2010, 'Buried' was one of Ryan Reynolds's most acclaimed films.
2010: Sesame Street and Buried
In 2010, Ryan Reynolds made a guest appearance on Sesame Street and starred in the film Buried.
2011: The Whale Acclaim
According to Rotten Tomatoes, in 2011, 'The Whale' was one of Ryan Reynolds's most acclaimed films.
2011: Green Lantern and The Change-Up
In 2011, Ryan Reynolds played the titular character in Green Lantern and starred in The Change-Up. Reynolds also executive-produced the documentary film The Whale in 2011.
2012: Starred in Safe House and cameo in Ted
In 2012, Ryan Reynolds starred in the action thriller "Safe House" alongside Denzel Washington, playing a CIA agent named Matt Weston, and made a cameo appearance in the comedy film "Ted".
2013: Starred in The Croods and Turbo
In 2013, Reynolds voiced Guy in DreamWorks' animated film "The Croods" and starred as Turbo, a garden snail who gains superspeed, in the movie "Turbo".
2013: Starred in R.I.P.D.
In 2013, Ryan Reynolds played Nick Walker in "R.I.P.D.", a film that was a box-office bomb and received negative reviews.
2014: Roles in The Voices and The Captive
In 2014, Ryan Reynolds starred in "The Voices" as Jerry Hickfang, a factory worker with schizophrenia, and portrayed Matthew in the psychological thriller "The Captive", both of which received mixed to negative reception.
2014: Hollywood Reporter calls Reynolds a popular actor
In 2014, The Hollywood Reporter's Richard Newby recognized Ryan Reynolds as 'one of Hollywood's most popular actors' for nearly two decades, noting his diverse range of roles, primarily in comedy, action, and superhero films.
2015: Mississippi Grind Acclaim
According to Rotten Tomatoes, in 2015, 'Mississippi Grind' was one of Ryan Reynolds's most acclaimed films.
2015: Starred in Mississippi Grind, Woman in Gold and Self/less
In 2015, Ryan Reynolds played Curtis in "Mississippi Grind", E. Randol Schoenberg in "Woman in Gold", and also starred in the science fiction film "Self/less", which was critically panned.
December 15, 2016: Received Star on Hollywood Walk of Fame
On December 15, 2016, Ryan Reynolds received a star on the Hollywood Walk of Fame at 6801 Hollywood Boulevard, a significant recognition of his contributions to the film industry.
2016: Deadpool Acclaim
According to Rotten Tomatoes, in 2016, 'Deadpool' was one of Ryan Reynolds's most acclaimed films.
2016: Starring role in Deadpool
In 2016, Ryan Reynolds achieved critical and commercial success with the superhero film "Deadpool", which he heavily contributed to the development of. The film grossed $782 million and received positive reviews, with many critics praising Reynolds's performance.
2016: Golden Globe Nomination for Deadpool
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 began, leading to the release of "Deadpool 2" in 2018.
2017: Reunited with Espinosa in Life and starred in The Hitman's Bodyguard
In 2017, Ryan Reynolds reunited with Daniel Espinosa in the science fiction film "Life", and starred in the action comedy "The Hitman's Bodyguard" as Michael Bryce.
2017: The Hitman's Bodyguard released
In 2017, Ryan Reynolds starred in The Hitman's Bodyguard as Michael Bryce
January 2018: Launched Maximum Effort and development of Clue
In January 2018, Ryan Reynolds launched the production company Maximum Effort and began development of a live-action adaptation of the board game "Clue".
February 2018: Acquired stake in Aviation American Gin
In February 2018, Ryan Reynolds acquired a stake in Aviation American Gin and oversaw the brand's creative direction.
2018: Deadpool 2 Acclaim
According to Rotten Tomatoes, in 2018, 'Deadpool 2' was one of Ryan Reynolds's most acclaimed films.
2018: Grammy Nomination for Deadpool 2 Soundtrack
In 2018, Ryan Reynolds received a Grammy nomination for Best Compilation Soundtrack for Visual Media for the soundtrack of 'Deadpool 2'.
November 2019: Purchased stake in Mint Mobile
In November 2019, Ryan Reynolds purchased an ownership stake in Mint Mobile, holding between 20% and 25%.
2019: Voiced Detective Pikachu and starred in 6 Underground
In 2019, Ryan Reynolds voiced the titular character in "Detective Pikachu", an adaptation of the video game, and starred in Michael Bay's action film "6 Underground" as the leader of a group fighting an evil dictator.
May 2020: Reading of James and the Giant Peach
In May 2020, Ryan Reynolds joined a group of celebrities in reading an installment of Roald Dahl's "James and the Giant Peach" to support Partners In Health in its efforts to combat COVID-19.
July 2020: Offered reward for stolen teddy bear
In July 2020, Ryan Reynolds offered a reward for the return of a stolen teddy bear containing a recording of a deceased mother's message, which was later recovered.
September 2020: Talks to purchase Wrexham
In September 2020, the Wrexham Supporters Trust announced that Ryan Reynolds and Rob McElhenney were in talks to purchase the Welsh soccer club Wrexham.
November 2020: Confirmed takeover of Wrexham
In November 2020, the takeover of Wrexham by Ryan Reynolds and Rob McElhenney was confirmed.
2020: The Croods: A New Age Acclaim
According to Rotten Tomatoes, in 2020, 'The Croods: A New Age' was one of Ryan Reynolds's most acclaimed films.
2020: Reynolds reflects on The Voices
In 2020, Ryan Reynolds described the 2014 film "The Voices" as one of his favorite movies he's ever done, despite it not getting its due recognition.
2020: Joined Match Group board and sold Aviation American Gin
In 2020, Ryan Reynolds joined the board of Match Group and later sold Aviation American Gin to Diageo in a deal valued at up to $610 million.
2020: Reprised voice role in The Croods: A New Age and Hitman's Wife's Bodyguard
In 2020, Ryan Reynolds reprised his role as the voice of Guy in "The Croods: A New Age" and as Michael Bryce in "Hitman's Wife's Bodyguard", a sequel to The Hitman's Bodyguard.
2020: Listed in Celebrity 100 and Second Highest Paid Actor
In 2020, Ryan Reynolds was listed in Forbes' Celebrity 100 list and was ranked as the second-highest-paid actor in the world by the same magazine, with earnings of $71.5 million.
February 2021: Approved takeover of Wrexham
In February 2021, Ryan Reynolds and Rob McElhenney's takeover of the Wrexham soccer club received approval from the Financial Conduct Authority.
June 23, 2021: Maximum Effort's marketing division acquired by MNTN Software
On June 23, 2021, Maximum Effort's marketing division was spun off into a separate company and acquired by MNTN Software.
October 2021: Announced sabbatical
In October 2021, Ryan Reynolds announced he was taking "a little sabbatical" from his work after the production of Spirited.
November 26, 2021: Honored with Governor General Performing Arts Award
On November 26, 2021, Mary Simon, governor general of Canada, honored Ryan Reynolds with a Governor General Performing Arts Award, celebrating his achievements in the performing arts.
2021: Free Guy Acclaim
According to Rotten Tomatoes, in 2021, 'Free Guy' was one of Ryan Reynolds's most acclaimed films.
2021: Starred in Free Guy and Red Notice
In 2021, Ryan Reynolds starred in "Free Guy", portraying a non-playable character who becomes self-aware, and in "Red Notice" as a renowned art thief alongside Dwayne Johnson and Gal Gadot.
March 2022: Donation to Water First
In March 2022, Ryan Reynolds and Blake Lively donated $500,000 to Water First, an organization providing Indigenous communities in Canada with access to clean water.
October 2022: Humanitarian Award
In October 2022, Ryan Reynolds was honoured with the Academy of Canadian Cinema and Television's Humanitarian Award at the 11th Canadian Screen Awards.
2022: Pledge for Ukrainian refugees
Following the 2022 Russian invasion of Ukraine, Ryan Reynolds and Blake Lively pledged to match donations of up to $1 million for Ukrainian refugees.
2022: Invested in companies and pursued ownership of Ottawa Senators
In 2022, Ryan Reynolds invested in Wealthsimple, 1Password, and FuboTV, and briefly pursued ownership of the National Hockey League's Ottawa Senators.
2022: Starred in The Adam Project and sabbatical announcement
In 2022, Ryan Reynolds starred in "The Adam Project" and announced he was taking a "little sabbatical" after the production of "Spirited".
2022: Welcome to Wrexham
In 2022, Welcome to Wrexham, the television series documenting Ryan Reynolds' co-ownership of Welsh soccer club Wrexham, premiered and won an Emmy Award.
March 2023: T-Mobile acquired Mint Mobile
In March 2023, T-Mobile announced its acquisition of Mint Mobile in a deal worth up to $1.35 billion, in which Ryan Reynolds had a stake.
April 2023: Invested in Nuvei
In April 2023, Ryan Reynolds invested in Canadian payments technology company Nuvei.
April 2023: Reynolds writes dialogue for It Ends with Us
In April 2023, Ryan Reynolds wrote a significant portion of dialogue for a rooftop scene in 'It Ends with Us' for Lively without the director Justin Baldoni's knowledge, sparking speculation about a rift.
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, supporting actors facing financial hardship.
August 2023: Recipient of the Order of British Columbia
In August 2023, Ryan Reynolds was announced as a recipient of the Order of British Columbia, the highest honor in British Columbia.
October 2023: Donation to 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, becoming the first celebrities to publicly contribute financial aid to both sides amid the Israel–Hamas war.
November 2023: Scheduled to Receive Order of British Columbia
In November 2023, Ryan Reynolds and his fellow honorees were scheduled to receive the Order of British Columbia at a ceremony in Victoria.
August 2024: Leading box office with separate films
In August 2024, Ryan Reynolds and his wife, Blake Lively, became the first married Hollywood couple since Bruce Willis and Demi Moore in 1990 to have separate films leading the box office on the same weekend, with "Deadpool & Wolverine" and "It Ends with Us" claiming the number one and two spots.
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 and other U.S. regions affected by the hurricanes Helene and Milton.
December 19, 2024: Appointed an Officer of the Order of Canada
On December 19, 2024, Ryan Reynolds was appointed an Officer of the Order of Canada, acknowledging his achievements in film and his philanthropic contributions.
2024: Deadpool & Wolverine Acclaim
According to Rotten Tomatoes, in 2024, 'Deadpool & Wolverine' was one of Ryan Reynolds's most acclaimed films.
2024: Second-Highest-Paid Actor and Hottest Men List
In 2024, Ryan Reynolds was again listed by Forbes as the second-highest-paid actor globally, earning $85 million. He was also included on Harper's Bazaar's list of the 50 Hottest Men of All Time.
2024: Grammy Nomination for Deadpool & Wolverine Soundtrack
In 2024, Ryan Reynolds was nominated again for the soundtrack of 'Deadpool & Wolverine' for a Grammy Award.
2024: It Ends with Us Production Controversy
In 2024, the production of 'It Ends with Us' was embroiled in controversy due to conflicts between Lively and the film's director, Justin Baldoni.
September 2025: Films Gross Over $6.6 Billion Worldwide
As of September 2025, Ryan Reynolds's films have collectively grossed over $6.6 billion worldwide, according to The Numbers, marking a major milestone in his career.
2050: Character portrayal in The Adam Project
In 2050, Ryan Reynolds's character in The Adam Project, Adam Reed, is a time pilot.
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