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, entrepreneur, and producer. He is best known for his roles in comedic and superhero films, achieving recognition as one of the highest-paid actors globally in both 2020 and 2024. He has received a Primetime Emmy Award and nominations for two Grammy Awards and a Golden Globe Award. Films in which he has had a leading role have grossed $6.5 billion worldwide.
2000: Deadpool film in development
As early as 2000, a film based on Deadpool was in development.
2004: Harold & Kumar Go to White Castle
According to review aggregation website Rotten Tomatoes, Harold & Kumar Go to White Castle (2004) is one of 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 one of 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 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 developing a "Deadpool" film.
2010: Buried
According to review aggregation website Rotten Tomatoes, Buried (2010) is one of Ryan Reynolds's most acclaimed films.
2011: The Whale
According to review aggregation website Rotten Tomatoes, The Whale (2011) is one of Ryan Reynolds's most acclaimed films.
2012: Starred 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. 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 that was a box-office bomb and panned by critics.
2013: Voiced roles in The Croods and Turbo
In 2013, Ryan Reynolds voiced Guy in DreamWorks' "The Croods," and the titular character, Turbo, in DreamWorks' "Turbo."
2014: Starred in The Voices and The Captive
In 2014, Ryan Reynolds starred in the horror comedy "The Voices" as Jerry Hickfang, and also starred in the psychological thriller "The Captive" as Matthew.
2014: Hollywood's Most Popular Actor
In 2014, The Hollywood Reporter's Richard Newby recognized Ryan Reynolds as "one of Hollywood's most popular actors for nearly 20 years", acknowledging his diverse range of roles, predominantly in comedy, action, and superhero films.
2015: Mississippi Grind
According to review aggregation website Rotten Tomatoes, Mississippi Grind (2015) is one of Ryan Reynolds's most acclaimed films.
2015: Starred in Mississippi Grind, Woman in Gold, and Self/less
In 2015, Ryan Reynolds starred as Curtis in "Mississippi Grind", portrayed E. Randol Schoenberg in "Woman in Gold", and starred in the science fiction film "Self/less".
2016: Deadpool
According to review aggregation website Rotten Tomatoes, Deadpool (2016) is one of Ryan Reynolds's most acclaimed films.
2016: Critical and commercial success with Deadpool
In 2016, Ryan Reynolds achieved significant critical and commercial success with the superhero film "Deadpool", grossing $782 million.
2016: Starred in Criminal
In 2016, Ryan Reynolds had a supporting role in the action thriller "Criminal" as Bill Pope, a character who is tortured and killed early in the film.
June 2017: Filming for Deadpool 2 started
In June 2017, filming for the sequel to "Deadpool" began.
2017: Starred in Life and The Hitman's Bodyguard
In 2017, Reynolds reunited with Daniel Espinosa in the science fiction Life. Reynolds also starred in Patrick Hughes's action comedy film The Hitman's Bodyguard.
January 2018: Launched Maximum Effort and developing Clue
In January 2018, Ryan Reynolds launched the production company Maximum Effort and announced 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, overseeing the brand's creative direction.
2018: Deadpool 2
According to review aggregation website Rotten Tomatoes, Deadpool 2 (2018) is one of 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.
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: Joined 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.
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 recovered within a few days.
September 2020: Talks to purchase Wrexham soccer club
In September 2020, it was 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
According to review aggregation website Rotten Tomatoes, The Croods: A New Age (2020) is one of Ryan Reynolds's most acclaimed films.
2020: Described The Voices as a favorite movie
In 2020, Ryan Reynolds described the movie "The Voices" as "one of my favorite movies I've ever done" despite it not getting its day in court.
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 starred in Hitman's Wife's Bodyguard
In 2020, Ryan Reynolds reprised his voice role as Guy in "The Croods: A New Age" and reprised the role of Michael Bryce in "Hitman's Wife's Bodyguard".
February 2021: Approval from Financial Conduct Authority for Wrexham purchase
In February 2021, Ryan Reynolds and Rob McElhenney received approval from the Financial Conduct Authority for their purchase of the Welsh soccer club Wrexham.
June 23, 2021: Maximum Effort's marketing division acquired
On June 23, 2021, Maximum Effort's marketing division was spun off into a separate company and acquired by MNTN Software.
October 2021: Announced a sabbatical
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 one of Ryan Reynolds's most acclaimed films.
2021: Starred in Free Guy and Red Notice
In 2021, Ryan Reynolds starred in "Free Guy" and "Red Notice".
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: Honoured 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: Pursued ownership of Ottawa Senators
In 2022, Reynolds 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" and "Spirited".
2022: Welcome to Wrexham
In 2022, the television documentary series Welcome to Wrexham covering the process of Ryan Reynolds and Rob McElhenney's investment in Wrexham started airing.
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, Ryan Reynolds invested in the Canadian payments technology company Nuvei.
August 2023: Donated to SAG-AFTRA Foundation
In August 2023, Ryan Reynolds and Blake Lively donated $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: Films led box office
In August 2024, Ryan Reynolds and 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. Their respective films, "Deadpool & Wolverine" and "It Ends with Us" claimed the number one and two spots.
October 2024: Donated 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.
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 review aggregation website Rotten Tomatoes, Deadpool & Wolverine (2024) is one of Ryan Reynolds's most acclaimed films.
2025: Film Grosses
As of 2025, Ryan Reynolds's films have grossed over $6.5 billion worldwide according to The Numbers.
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