History of Ryan Reynolds in Timeline
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.
1961: James and the Giant Peach published
In 1961, Roald Dahl's book James and the Giant Peach was published.
2000: Development of Deadpool film begins
As early as 2000, the superhero film Deadpool had been in development.
2002: Began Dating Alanis Morissette
In 2002, Ryan Reynolds began dating singer Alanis Morissette after meeting at Drew Barrymore's birthday party, marking the beginning of their relationship.
June 2004: Engagement Announcement
In June 2004, Ryan Reynolds and Alanis Morissette announced their engagement, signifying a deeper commitment in their relationship.
2004: Harold & Kumar Go to White Castle acclaimed film
In 2004, Ryan Reynolds starred in the acclaimed film Harold & Kumar Go to White Castle.
February 2007: Engagement Called Off
In February 2007, representatives confirmed that Ryan Reynolds and Alanis Morissette had mutually decided to call their engagement off, ending their relationship.
April 2007: Began Dating Scarlett Johansson
In April 2007, shortly after his breakup with Alanis Morissette, Ryan Reynolds began dating actress Scarlett Johansson, marking the beginning of a new relationship.
2007: People's Sexiest Men Alive
In 2007, Ryan Reynolds was featured in People's Sexiest Men Alive list, acknowledging his appeal.
May 2008: Engagement Announcement
In May 2008, Ryan Reynolds and Scarlett Johansson announced their engagement, signifying a deeper commitment in their relationship.
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.
2009: People's Sexiest Men Alive List
In 2009, Ryan Reynolds was again featured in People's Sexiest Men Alive list.
July 2010: Met Blake Lively
In July 2010, Ryan Reynolds first met Blake Lively while filming Green Lantern (2011), where they costarred, marking the beginning of their acquaintance.
December 14, 2010: Separation Announcement
On December 14, 2010, Ryan Reynolds and Scarlett Johansson announced their separation, indicating the end of their marriage.
2010: Buried acclaimed film
In 2010, Ryan Reynolds starred in the acclaimed film Buried.
2010: Sexiest Man Alive
In 2010, Ryan Reynolds was named Sexiest Man Alive by People, recognizing his widespread appeal.
July 2011: Divorce Finalized
In July 2011, the divorce between Ryan Reynolds and Scarlett Johansson was finalized, legally ending their marriage.
October 2011: Began Dating Blake Lively
In October 2011, Ryan Reynolds and Blake Lively began dating, transitioning their relationship from colleagues to partners.
2011: The Whale acclaimed film
In 2011, Ryan Reynolds starred in the acclaimed film The Whale.
September 9, 2012: Married Blake Lively
On September 9, 2012, Ryan Reynolds married Blake Lively at Boone Hall Plantation in Mount Pleasant, South Carolina, solidifying their relationship.
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.
2015: Death of Father
In 2015, Ryan Reynolds's father, James, passed away after battling Parkinson's disease for twenty years, marking a personal loss.
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: Golden Globe Nomination for Deadpool
For his role in Deadpool in 2016, Ryan Reynolds received a Golden Globe nomination for Best Actor in a Motion Picture – Musical or Comedy.
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.
2017: Time's 100 Most Influential People
In 2017, Time included Ryan Reynolds in its list of the 100 most influential people in the world, acknowledging his widespread impact.
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: Grammy nomination for Deadpool 2 soundtrack
For the soundtrack of Deadpool 2 in 2018, Ryan Reynolds received a Grammy nomination for Best Compilation Soundtrack for Visual Media.
2018: Deadpool 2 released
In 2018, Deadpool 2 was released and became a commercial success, grossing $715 million.
2018: Acquires stake in Aviation American Gin
In 2018, Ryan Reynolds expanded into business ventures by acquiring a stake in Aviation American Gin and oversaw the brand's creative direction.
2018: Discussed Anxiety Struggles
In 2018, Ryan Reynolds openly discussed his lifelong struggle with anxiety, revealing that he often conducted interviews in character as Deadpool to help manage his fears, highlighting his personal challenges.
November 2019: Purchases stake in Mint Mobile
In November 2019, Ryan Reynolds purchased an ownership stake in Mint Mobile, holding between 20% and 25%.
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.
September 2020: Talks to purchase Wrexham announced
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 football club Wrexham.
November 2020: Takeover of Wrexham confirmed
In November 2020, Ryan Reynolds and Rob McElhenney's takeover of Wrexham was confirmed.
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: Celebrity 100 List
In 2020, Ryan Reynolds appeared in the Celebrity 100 list by Forbes, being listed as the eighteenth-most-powerful person and second-highest-paid actor in the world, with earnings of $71.5 million, recognizing his financial success and influence.
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: Joins Match Group board and sells 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: Apology for Venue Choice
In 2020, Ryan Reynolds publicly apologized and expressed deep regret for choosing Boone Hall Plantation, a venue with ties to slavery, for his wedding with Blake Lively, acknowledging the historical insensitivity.
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.
February 2021: Takeover of Wrexham receives approval
In February 2021, Ryan Reynolds and Rob McElhenney's takeover of Wrexham earned 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: 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: Pursues ownership of Ottawa Senators
In 2022, Ryan Reynolds briefly pursued ownership of the National Hockey League's Ottawa Senators but withdrew his bid in the middle of 2023.
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.
2022: Welcome to Wrexham documentary series begins
In 2022, the process of Ryan Reynolds and Rob McElhenney's investment in Wrexham was covered by the television documentary series Welcome to Wrexham.
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, in which Ryan Reynolds owned a stake.
April 2023: Invests in Nuvei
In April 2023, Canadian payments technology company Nuvei announced that Ryan Reynolds had invested in the company.
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.
November 2024: Taylor Swift as Godmother
In November 2024, Ryan Reynolds confirmed that Taylor Swift is the godmother to his three daughters, showcasing the close friendship between the families.
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: Second-Highest-Paid Actor
In 2024, Forbes listed Ryan Reynolds as the second-highest-paid actor in the world, with earnings of $85 million, highlighting his continued financial success.
2024: Anxiety Makes Him "Quiet" and "Shy"
In 2024, Ryan Reynolds reiterated that his anxiety makes him "quiet" and "shy" outside of acting, showing vulnerability about his personal struggles.
2024: Deadpool & Wolverine acclaimed film
In 2024, Ryan Reynolds starred in the acclaimed film Deadpool & Wolverine.
2024: Grammy nomination for Deadpool & Wolverine soundtrack
Ryan Reynolds was later nominated again for the soundtrack of Deadpool & Wolverine in 2024.
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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