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 roles in comedic and superhero films. He achieved the distinction of being the world's second-highest-paid actor in both 2020 and 2024. His work has earned him several accolades, including two Primetime Emmy Awards and nominations for two Grammy Awards and a Golden Globe Award. Films in which he starred as a leading actor have collectively grossed $6.6 billion globally, marking his significant impact on the film industry.
2000: Deadpool film development began
Since as early as 2000, development of the "Deadpool" film has been ongoing, leading to Ryan Reynolds's involvement.
2004: Harold & Kumar Go to White Castle Film
According to review aggregation website Rotten Tomatoes, one of Ryan Reynolds's most acclaimed films is Harold & Kumar Go to White Castle in 2004.
2008: Ran the New York City Marathon
In 2008, Ryan Reynolds ran the New York City Marathon for Team Fox to support the Michael J. Fox Foundation.
2009: Adventureland Film
According to review aggregation website Rotten Tomatoes, one of Ryan Reynolds's most acclaimed films is Adventureland in 2009.
2009: Joined the board of the 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", which later led to his heavy involvement in the development of the "Deadpool" film.
2010: Buried Film
According to review aggregation website Rotten Tomatoes, one of Ryan Reynolds's most acclaimed films is Buried in 2010.
2011: The Whale Film
According to review aggregation website Rotten Tomatoes, one of Ryan Reynolds's most acclaimed films is 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 CIA agent Matt Weston. His performance received praise. He also made a cameo appearance as Jared in the comedy "Ted" in 2012.
2013: Starring voice roles in The Croods and Turbo
In 2013, Ryan Reynolds had starring voice roles in two DreamWorks Animation feature films. He voiced Guy in "The Croods", and Turbo in "Turbo".
2013: Played Nick Walker 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.
2014: Hollywood's most popular actors
In 2014, Richard Newby of The Hollywood Reporter called Ryan Reynolds "one of Hollywood's most popular actors for nearly 20 years", recognizing his diverse range of roles, particularly in comedy, action, and superhero films.
2014: Roles in The Voices and The Captive
In 2014, Ryan Reynolds took on several roles in "The Voices", starring as Jerry Hickfang. He also portrayed Matthew in the psychological thriller "The Captive", which received negative reception.
2015: Mississippi Grind Film
According to review aggregation website Rotten Tomatoes, one of Ryan Reynolds's most acclaimed films is Mississippi Grind in 2015.
2015: Starred in Mississippi Grind, Woman in Gold, and Self/less
In 2015, Ryan Reynolds starred as Curtis in "Mississippi Grind". He also portrayed E. Randol Schoenberg in "Woman in Gold" and starred in "Self/less", which was critically panned.
December 15, 2016: 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.
2016: Deadpool Film
According to review aggregation website Rotten Tomatoes, one of Ryan Reynolds's most acclaimed films is Deadpool in 2016.
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. Critics praised Reynolds's performance.
2016: Supporting role in Criminal
In 2016, Ryan Reynolds had a supporting role in the action thriller "Criminal", where he played Bill Pope. The film received negative reviews.
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 a sequel to Deadpool started.
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". He also starred in "The Hitman's Bodyguard" as Michael Bryce.
2017: Starred in The Hitman's Bodyguard
In 2017, Ryan Reynolds starred in "The Hitman's Bodyguard" as Michael Bryce.
2017: Time 100
In 2017, Ryan Reynolds was named as one of the 100 most influential people in the world by Time magazine, landing him on the Time 100 list.
January 2018: Launched Maximum Effort and Clue adaptation in development
In January 2018, Ryan Reynolds launched the production company Maximum Effort and signed a three-year first-look deal with Fox. Also, 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 Film
According to review aggregation website Rotten Tomatoes, one of Ryan Reynolds's most acclaimed films is Deadpool 2 in 2018.
2018: Grammy Nomination
For the soundtrack of Deadpool 2, Ryan Reynolds received a Grammy nomination for Best Compilation Soundtrack for Visual Media in 2018.
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: Starred in Detective Pikachu and 6 Underground
In 2019, Ryan Reynolds voiced the titular character in "Detective Pikachu", an adaptation of the video game. He also starred in Michael Bay's "6 Underground".
May 2020: Reading of James and the Giant Peach for charity
In May 2020, Ryan Reynolds joined other celebrities in reading an installment of Roald Dahl's James and the Giant Peach to support Partners In Health in combating COVID-19.
July 2020: Offered reward for stolen teddy bear
In July 2020, Ryan Reynolds and George Stroumboulopoulos offered $5,000 for the return of a stolen teddy bear containing a recording of a deceased mother's message. The bear was recovered.
September 2020: Talks to purchase Wrexham
In September 2020, the Wrexham Supporters Trust announced that a business partnership comprising Ryan Reynolds and Rob McElhenney was 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 the Welsh soccer club Wrexham was confirmed.
2020: The Croods: A New Age Film
According to review aggregation website Rotten Tomatoes, one of Ryan Reynolds's most acclaimed films is The Croods: A New Age in 2020.
2020: Reflection on The Voices
In 2020, Ryan Reynolds described the film "The Voices" as "one of my favorite movies I've ever done [...] never really got its day in court, but man, it's weird and fun and beautiful".
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 Guy in "The Croods: A New Age" and as Michael Bryce in "Hitman's Wife's Bodyguard".
2020: Celebrity 100 List
In 2020, Ryan Reynolds was listed in Forbes' Celebrity 100 list as the eighteenth-most-powerful person in the world. The magazine also listed him as the second-highest-paid actor in the world that year, with earnings of $71.5 million.
2020: American Citizenship and First Vote
Ryan Reynolds attained American citizenship around 2018, and voted for the first time in the 2020 presidential election.
February 2021: Wrexham takeover 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".
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 Film
According to review aggregation website Rotten Tomatoes, one of Ryan Reynolds's most acclaimed films is Free Guy in 2021.
2021: Starred in Free Guy and Red Notice
In 2021, Ryan Reynolds starred in "Free Guy", portraying a non-playable character. He also starred in "Red Notice" 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: Received Humanitarian Award and donated to Feeding America
In October 2022, Ryan Reynolds was honored with the Academy of Canadian Cinema and Television's Humanitarian Award. The couple also donated $1 million to Feeding America.
2022: Pledged donation match 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: Investments in Wealthsimple, 1Password, and FuboTV, pursuit of Ottawa Senators
In 2022, Ryan Reynolds invested in several companies, including Wealthsimple, 1Password and FuboTV. He also briefly pursued ownership of the National Hockey League's Ottawa Senators.
2022: Starred in The Adam Project and production of Spirited
In 2022, Ryan Reynolds starred in "The Adam Project". He also worked on "Spirited", a Christmas musical comedy.
2022: Welcome to Wrexham documentary series
The process of Ryan Reynolds and Rob McElhenney's investment in Wrexham was covered in the television documentary series "Welcome to Wrexham" starting in 2022.
March 2023: T-Mobile acquisition of Mint Mobile announced
In March 2023, T-Mobile announced its acquisition of Mint Mobile in a deal worth up to $1.35 billion.
April 2023: Investment in Nuvei announced
In April 2023, Canadian payments technology company Nuvei announced that Ryan Reynolds had invested in the company.
April 2023: Rooftop Scene Dialogue
In April 2023, Ryan Reynolds wrote a significant portion of dialogue for a rooftop scene featuring Blake Lively in It Ends with Us without the director's knowledge.
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.
August 2023: Order of British Columbia Recipient
In August 2023, Ryan Reynolds was announced as a recipient of the Order of British Columbia, British Columbia's highest honour.
October 2023: Donated 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 honorees were scheduled to receive the Order of British Columbia award at a ceremony in Victoria.
August 2024: Deadpool & Wolverine and It Ends with Us lead box office
In August 2024, Ryan Reynolds and his wife, Blake Lively, became the first married Hollywood couple since Bruce Willis and Demi Moore 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: Donation 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: 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 Film
According to review aggregation website Rotten Tomatoes, one of Ryan Reynolds's most acclaimed films is Deadpool & Wolverine in 2024.
2024: Second-highest-paid actor
In 2024, Ryan Reynolds was again listed by Forbes as the second-highest-paid actor in the world, earning $85 million.
2024: Grammy Nomination for Deadpool & Wolverine Soundtrack
Ryan Reynolds was nominated again for the soundtrack of Deadpool & Wolverine in 2024.
September 2025: Films Gross Over $6.6 Billion Worldwide
As of September 2025, Ryan Reynolds's films have grossed over $6.6 billion worldwide according to The Numbers.
2050: The Adam Project
In 2022, Ryan Reynolds starred in Levy's science fiction action comedy The Adam Project, portraying Adam Reed—a time pilot from 2050 who risks his life to uncover the truth regarding his wife's disappearance.
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