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 businessman celebrated for his roles in both comedic and superhero films. His movies have generated $6.5 billion globally, placing him among the highest-paid actors. He's won a Primetime Emmy Award and received nominations for two Grammy Awards and a Golden Globe Award, highlighting his versatility and success in the entertainment industry. Reynolds' ventures extend beyond acting, showcasing his entrepreneurial spirit.
2000: Development of Deadpool film begins
As early as 2000, the superhero film Deadpool had been in development.
2004: Harold & Kumar Go to White Castle acclaimed film
In 2004, Ryan Reynolds starred in the acclaimed film Harold & Kumar Go to White Castle.
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.
2009: Adventureland acclaimed film
In 2009, Ryan Reynolds starred in the acclaimed film Adventureland.
2010: Buried acclaimed film
In 2010, Ryan Reynolds starred in the acclaimed film Buried.
2011: The Whale acclaimed film
In 2011, Ryan Reynolds starred in the acclaimed film The Whale.
2012: Stars in Safe House and makes cameo in Ted
In 2012, Ryan Reynolds starred in the action thriller Safe House alongside Denzel Washington. Reynolds played Matt Weston, a CIA agent. Also in 2012, he made a cameo appearance as Jared in the comedy Ted.
2013: Voice roles in The Croods and Turbo, and stars in R.I.P.D.
In 2013, Ryan Reynolds had starring voice roles in two DreamWorks Animation films, The Croods, where he voiced Guy, and Turbo, where he voiced the titular character. Also in 2013, he played Nick Walker in R.I.P.D.
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.
2014: Hollywood's Most Popular Actors
In 2014, Richard Newby of The Hollywood Reporter noted that Ryan Reynolds had been one of Hollywood's most popular actors for nearly 20 years, acknowledging his sustained success in the industry.
2014: Roles in The Voices and The Captive
In 2014, Ryan Reynolds took on several roles in the horror comedy film The Voices. In the psychological thriller The Captive (2014), he portrays Matthew.
2015: Stars 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 Self/less.
2015: Mississippi Grind acclaimed film
In 2015, Ryan Reynolds starred in the acclaimed film Mississippi Grind.
December 15, 2016: Hollywood Walk of Fame Star
On December 15, 2016, Ryan Reynolds received a star on the Hollywood Walk of Fame, located at 6801 Hollywood Boulevard, marking a significant achievement in his career.
2016: A-lister Status with Deadpool
In 2016, Rotten Tomatoes recognized that Ryan Reynolds had established himself as an A-lister with the chops to play just about any part, reaching an even greater peak with his portrayal in Deadpool.
2016: Critical and Commercial Success with Deadpool
In 2016, Ryan Reynolds found significant critical and commercial success with the superhero film Deadpool. His performance earned universal acclaim and the film grossed $782 million.
2016: Supporting role in Criminal
In 2016, Ryan Reynolds had a supporting role in Ariel Vromen's action thriller Criminal, playing Bill Pope.
June 2017: Filming for Deadpool 2 begins
In June 2017, filming for a sequel to Deadpool started, eventually leading to the release of Deadpool 2 in 2018.
2017: Stars in The Hitman's Bodyguard
In 2017, Reynolds starred in Patrick Hughes's action comedy film The Hitman's Bodyguard as Michael Bryce.
January 2018: Launches Maximum Effort Production Company
In January 2018, Ryan Reynolds launched the production company Maximum Effort and signed a three-year first-look deal with Fox.
2018: Deadpool 2 released
In 2018, Deadpool 2 was released and became a commercial success, grossing $715 million.
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 action film 6 Underground.
May 2020: Reads 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 the global non-profit Partners In Health in its efforts to combat COVID-19.
July 2020: Offers 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.
2020: First Time Voting
Around 2018, Ryan Reynolds became an American citizen, and in 2020, he voted for the first time in the presidential election, marking his civic engagement.
2020: Reflects 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: Reprises role 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: The Croods: A New Age acclaimed film
In 2020, Ryan Reynolds starred in the acclaimed film The Croods: A New Age.
October 2021: Announces 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's Performing Arts Award
On November 26, 2021, Governor General Mary Simon honoured Ryan Reynolds with a Governor General's Performing Arts Award, recognizing his contributions to the performing arts.
2021: Stars in Free Guy and Red Notice
In 2021, Ryan Reynolds starred in Shawn Levy's contemporary fantasy Free Guy and in the action comedy film Red Notice.
2021: Free Guy acclaimed film
In 2021, Ryan Reynolds starred in the acclaimed film Free Guy.
March 2022: Pledges donations for Ukrainian refugees and donates to Water First
In March 2022, Ryan Reynolds and his wife, Blake Lively, pledged to match donations up to $1 million for Ukrainian refugees. Also in March 2022, the couple donated $500,000 to Water First.
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: Stars in The Adam Project and takes a sabbatical
In 2022, Ryan Reynolds starred in The Adam Project. In October 2021, he announced he was taking a "little sabbatical" from his work after the production of Spirited.
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, which is Canada's highest honour, recognizing his significant contributions.
November 2023: Ceremony in Victoria
In November 2023, Ryan Reynolds and fellow honorees were scheduled to receive the Order of British Columbia award at a ceremony in Victoria.
August 2024: Films lead box office on same weekend
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.
October 2024: Donates to Feeding America
In October 2024, Ryan Reynolds and Blake Lively voluntarily donated $1 million to the non-profit organization Feeding America to aid relief efforts in Florida and other U.S. regions affected by the October 2024 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 philanthropic contributions.
2024: Deadpool & Wolverine acclaimed film
In 2024, Ryan Reynolds starred in the acclaimed film Deadpool & Wolverine.
2025: Films Gross Over $6.5 Billion
As of 2025, Ryan Reynolds's films have grossed over $6.5 billion worldwide according to The Numbers, indicating his significant box office success.
2050: Plays Adam Reed in The Adam Project
In the movie The Adam Project Ryan Reynolds portrays Adam Reed—a time pilot from 2050 who risks his life to uncover the truth regarding his wife's disappearance.
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