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 and American actor, producer, and businessman. Primarily recognized for his roles in comedic and superhero films, Reynolds was the second-highest-paid actor globally in both 2020 and 2024. His films have collectively grossed over $6.5 billion worldwide. He has received various awards, including a Primetime Emmy Award, and has been nominated for two Grammy Awards and a Golden Globe Award, highlighting his broad success in the entertainment industry.
2000: Deadpool Film Development Begins
Development of a film based on Deadpool, starring Ryan Reynolds, began as early as 2000.
2004: Harold & Kumar Go to White Castle
According to review aggregation website Rotten Tomatoes, Harold & Kumar Go to White Castle (2004) is among Ryan Reynolds's most acclaimed films.
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
According to review aggregation website Rotten Tomatoes, Adventureland (2009) is among Ryan Reynolds's most acclaimed films.
2009: Joined Board of Michael J. Fox Foundation
In 2009, Ryan Reynolds joined the board of the Michael J. Fox Foundation and continues to support research for a cure.
2009: Portrayed 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 involvement in the development of a standalone Deadpool film.
2010: Buried
According to review aggregation website Rotten Tomatoes, Buried (2010) is among Ryan Reynolds's most acclaimed films.
2011: The Whale
According to review aggregation website Rotten Tomatoes, The Whale (2011) is among Ryan Reynolds's most acclaimed films.
2012: Starred in Safe House and Made a Cameo in Ted
In 2012, Ryan Reynolds starred in the action thriller Safe House alongside Denzel Washington, playing CIA agent Matt Weston. Also in 2012, he made a cameo appearance in the comedy Ted.
2013: Starred in R.I.P.D.
In 2013, Ryan Reynolds played Nick Walker in R.I.P.D., a film about a detective murdered by his partner. The film was a box-office bomb.
2013: Voiced Characters in The Croods and Turbo
In 2013, Ryan Reynolds voiced Guy in DreamWorks' The Croods, an inventive teenage caveboy, and Turbo, a garden snail with superspeed who dreams of racing in the Indianapolis 500 and 24 Hours of Le Mans. These roles expanded his presence in animated feature films in 2013.
2014: Hollywood's Most Popular Actor
In 2014, Richard Newby of The Hollywood Reporter recognized Ryan Reynolds as "one of Hollywood's most popular actors for nearly 20 years", noting his diverse range of roles, predominantly in comedy, action, and superhero films.
2014: Took on Roles in The Voices and The Captive
In 2014, Ryan Reynolds starred in the horror comedy film The Voices, playing Jerry Hickfang, a factory worker with schizophrenia. Also in 2014, he played Matthew in the psychological thriller The Captive, a father searching for his missing daughter.
2015: Mississippi Grind
According to review aggregation website Rotten Tomatoes, Mississippi Grind (2015) is among 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 starred in Self/less. These roles showcased his versatility across different film genres in 2015.
2016: Deadpool
According to review aggregation website Rotten Tomatoes, Deadpool (2016) is among Ryan Reynolds's most acclaimed films.
2016: Achieved Success with Deadpool
In 2016, Ryan Reynolds achieved significant critical and commercial success with the superhero film Deadpool, a project he had been developing since as early as 2000. The film became the ninth-highest-grossing film of 2016.
2016: Played Bill Pope in Criminal
In 2016, Ryan Reynolds had a supporting role as Bill Pope in the action thriller Criminal, where his character is killed early in the film.
June 2017: Filming Began for Deadpool 2
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 director Daniel Espinosa in the science fiction film Life, playing Rory Adams. Also in 2017, he starred in The Hitman's Bodyguard as Michael Bryce.
2017: Starred in The Hitman's Bodyguard
In 2017, he starred in The Hitman's Bodyguard as Michael Bryce.
January 2018: Launched Maximum Effort and Developed Clue Adaptation
In January 2018, Ryan Reynolds launched the production company Maximum Effort and signed a three-year first-look 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: Acquired Stake in Aviation American Gin
In February 2018, Ryan Reynolds acquired a stake in Aviation American Gin, taking on a role of overseeing the brand's creative direction.
2018: Deadpool 2
According to review aggregation website Rotten Tomatoes, Deadpool 2 (2018) is among Ryan Reynolds's most acclaimed films.
November 2019: Purchased Ownership 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 and starred in Michael Bay's action film 6 Underground.
May 2020: Read James and the Giant Peach to Support Partners In Health
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's efforts to combat COVID-19.
July 2020: Offered Reward for Stolen Teddy Bear
In July 2020, Ryan Reynolds and George Stroumboulopoulos each offered $5,000 for the return of a stolen teddy bear belonging to a Vancouver woman, which was later recovered.
September 2020: Began 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: 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 review aggregation website Rotten Tomatoes, The Croods: A New Age (2020) is among Ryan Reynolds's most acclaimed films.
2020: Described The Voices as a Favorite Movie
In 2020, Ryan Reynolds described the film The Voices as "one of my favorite movies I've ever done".
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 Roles 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.
February 2021: Takeover of Wrexham Approved
In February 2021, Ryan Reynolds and Rob McElhenney's takeover of Wrexham 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 After Spirited
In October 2021, Ryan Reynolds announced he was taking "a little sabbatical" from his work after the production of Spirited.
2021: Free Guy
According to review aggregation website Rotten Tomatoes, Free Guy (2021) is among 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, and Red Notice, playing a renowned art thief.
March 2022: Donated 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: Honored with 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: Pledged to Match Donations 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 fleeing the conflict.
2022: Invested in Various Companies and Pursued Ownership of Ottawa Senators
In 2022, Ryan Reynolds invested in several companies, including Wealthsimple, 1Password and FuboTV. Also in 2022, he briefly pursued ownership of the National Hockey League's Ottawa Senators.
2022: Starred in The Adam Project and Spirited
In 2022, Ryan Reynolds starred in The Adam Project, playing Adam Reed, and Spirited, a Christmas musical comedy. These roles continued his presence in both science fiction and comedy genres in 2022.
2022: Welcome to Wrexham Documentary Series
In 2022, the process of Ryan Reynolds and Rob McElhenney's investment in Wrexham was covered in the television documentary series Welcome to Wrexham.
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.
April 2023: Invested in Nuvei
In April 2023, Canadian payments technology company Nuvei announced that Ryan Reynolds had invested in the company.
August 2023: Donated to SAG-AFTRA Foundation
In August 2023, Ryan Reynolds and Blake Lively joined several other Hollywood couples in donating $1 million to the SAG-AFTRA Foundation's financial assistance program.
October 2023: Donated 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 in Israel and Gaza.
August 2024: Deadpool & Wolverine and It Ends with Us Lead Box Office
In August 2024, Ryan Reynolds and Blake Lively became the first married Hollywood couple since 1990 to have separate films leading the box office on the same weekend. Their respective films, Deadpool & Wolverine and It Ends with Us, claimed the number one and two spots. Deadpool & Wolverine also achieved commercial and critical success.
October 2024: Donated to Feeding America
In October 2024, Ryan Reynolds and Blake Lively donated $1 million to the non-profit organization Feeding America to aid relief efforts in Florida and other U.S. regions affected by the hurricanes Helene and Milton.
December 19, 2024: Appointed Officer of the Order of Canada
On December 19, 2024, Ryan Reynolds was appointed an Officer of the Order of Canada, recognizing his achievements in film and his philanthropic contributions.
2024: Deadpool & Wolverine
According to review aggregation website Rotten Tomatoes, Deadpool & Wolverine (2024) is among Ryan Reynolds's most acclaimed films.
2025: Box Office Success
As of 2025, Ryan Reynolds's films have grossed over $6.5 billion worldwide, according to The Numbers.
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