History of Ryan Reynolds in Timeline
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.
1907: Portrait of Adele Bloch-Bauer I Painted
In 1907, Gustav Klimt painted Portrait of Adele Bloch-Bauer I, which is featured in the 2015 film Woman in Gold, in which Reynolds starred.
1961: Publication 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 (published in 1961) to support Partners In Health's efforts to combat COVID-19.
1990: Last Married Couple with Separate Films Leading Box Office Prior to Reynolds and Lively
In August 2024, Reynolds and 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.
2000: Deadpool Film Development Begins
Development of a film based on Deadpool, starring Ryan Reynolds, began as early as 2000.
2002: Began Dating Alanis Morissette
In 2002, Ryan Reynolds began dating singer Alanis Morissette after meeting her at Drew Barrymore's birthday party.
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.
2004: Engagement to Alanis Morissette
In 2004, Ryan Reynolds and Alanis Morissette announced their engagement.
February 2007: Engagement Called Off
In February 2007, representatives for Ryan Reynolds and Alanis Morissette confirmed that they had mutually decided to call off their engagement.
April 2007: Began Dating Scarlett Johansson
In April 2007, shortly after his breakup with Alanis Morissette, Ryan Reynolds began dating actress Scarlett Johansson.
2007: People's Sexiest Men Alive
In 2007, Ryan Reynolds was featured in People magazine's Sexiest Men Alive list.
May 2008: Engagement to Scarlett Johansson
In May 2008, Ryan Reynolds and Scarlett Johansson announced their engagement.
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.
2009: People's Sexiest Men Alive
In 2009, Ryan Reynolds was again featured in People magazine's Sexiest Men Alive list.
July 2010: First Meeting with Blake Lively
In July 2010, Ryan Reynolds first met Blake Lively while filming "Green Lantern" (2011), in which they were costars.
December 14, 2010: Separation Announced
On December 14, 2010, Ryan Reynolds and Scarlett Johansson announced their separation.
2010: Buried
According to review aggregation website Rotten Tomatoes, Buried (2010) is among Ryan Reynolds's most acclaimed films.
2010: Sexiest Man Alive
In 2010, Ryan Reynolds was named People magazine's Sexiest Man Alive.
July 2011: Divorce Finalized
In July 2011, the divorce between Ryan Reynolds and Scarlett Johansson was finalized.
October 2011: Began Dating Blake Lively
In October 2011, Ryan Reynolds and Blake Lively began dating.
2011: The Whale
According to review aggregation website Rotten Tomatoes, The Whale (2011) is among Ryan Reynolds's most acclaimed films.
September 9, 2012: Marriage to Blake Lively
On September 9, 2012, Ryan Reynolds and Blake Lively married at Boone Hall Plantation in Mount Pleasant, South Carolina.
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.
2015: Death of Father
In 2015, Ryan Reynolds's father, James, passed away after a twenty-year battle with Parkinson's disease. Reynolds used humour to cope with his grief.
December 15, 2016: Star on the 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
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.
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 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: Time 100
In 2017, Ryan Reynolds was featured in the Time 100, Time magazine's annual list of the 100 most influential people in the world.
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.
2018: Grammy Nomination
In 2018, Ryan Reynolds received a Grammy nomination for Best Compilation Soundtrack for Visual Media for the soundtrack of Deadpool 2.
2018: Anxiety Management
In 2018, Ryan Reynolds revealed his lifelong struggle with anxiety and mentioned that he often conducted interviews in character as Deadpool to manage his fears.
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: First Time Voting
Around 2018, Ryan Reynolds attained American citizenship, and in 2020, he voted for the first time in the presidential election.
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.
2020: Celebrity 100 List
In 2020, Ryan Reynolds was included in Forbes' Celebrity 100 list as the eighteenth-most-powerful person globally. He was also listed as the second-highest-paid actor in the world, earning $71.5 million.
2020: Regret Over Wedding Venue
In 2020, following civil rights protests, Ryan Reynolds publicly apologized and expressed deep regret for choosing Boone Hall Plantation as his wedding venue due to its ties to slavery. The couple later renewed their vows at home in New York.
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.
November 26, 2021: Governor General's Performing Arts Award
On November 26, 2021, Ryan Reynolds was honoured with a Governor General's Performing Arts Award by Mary Simon, governor general of Canada.
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.
April 2023: Dialogue Contribution
In April 2023, Ryan Reynolds wrote a significant portion of dialogue for a rooftop scene in "It Ends with Us" featuring Blake Lively, without the knowledge of the film's director, Justin Baldoni.
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
In August 2023, Ryan Reynolds was announced as a recipient of the Order of British Columbia, British Columbia's highest honour. He and his fellow honourees were scheduled to receive the award at a ceremony in Victoria in November 2023.
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.
November 2023: Order of British Columbia Ceremony
In November 2023, Ryan Reynolds and his fellow honourees were scheduled to receive the Order of British Columbia, British Columbia's highest honour, at a ceremony in Victoria.
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.
November 2024: Taylor Swift as Godmother
In November 2024, Ryan Reynolds confirmed that Taylor Swift is the godmother to his three daughters.
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.
2024: Second Highest Paid Actor
In 2024, Forbes again listed Ryan Reynolds as the second-highest-paid actor in the world, reporting his earnings at $85 million.
2024: Anxiety and Shyness
In 2024, Ryan Reynolds reiterated that his anxiety makes him "quiet" and "shy" outside of acting.
2024: Grammy Nomination
In 2024, Ryan Reynolds was nominated again for a Grammy award for the soundtrack of Deadpool & Wolverine.
2024: It Ends With Us Controversy
In 2024, the production of "It Ends with Us" faced controversy due to conflicts involving Blake Lively and director Justin Baldoni. The situation escalated after Reynolds wrote dialogue for a rooftop scene.
January 16, 2025: Lawsuit Filed Against Reynolds and Lively
On January 16, 2025, Justin Baldoni filed a $400 million civil lawsuit against Ryan Reynolds and Blake Lively, alleging extortion, defamation, and invasion of privacy related to the production of "It Ends With Us". Reynolds filed a motion to be dismissed from the lawsuit in March of the same year.
2025: Box Office Success
As of 2025, Ryan Reynolds's films have grossed over $6.5 billion worldwide, according to The Numbers.
2050: Character Adam Reed's Origin Year in The Adam Project
The Adam Project features Reynolds as Adam Reed, a time pilot from 2050, who time travels to uncover the truth regarding his wife's disappearance. 2050 is Adam Reed's origin year.
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