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, renowned for his roles in comedic and superhero films. He ranked as the world's second-highest-paid actor in both 2020 and 2024. Reynolds has garnered critical acclaim, including two Primetime Emmy Awards, and nominations for two Grammy Awards and a Golden Globe Award. As a leading actor, his films have collectively grossed $6.6 billion worldwide, demonstrating his significant impact on the entertainment industry.
1961: Mention of James and the Giant Peach
In May 2020, Reynolds joined a group of celebrities in reading an installment of Roald Dahl's 1961 book James and the Giant Peach to support the global non-profit organization Partners In Health.
1991: Career Start in Hillside
In 1991, Ryan Reynolds began his acting career in the Canadian teen soap opera Hillside, also known as Fifteen in the United States.
1993: Feature Film Debut in Ordinary Magic
In 1993, Ryan Reynolds made his feature film debut in the coming-of-age drama Ordinary Magic, playing Jeffrey.
1993: Hillside role ends
In 1993, Ryan Reynolds' role in Hillside came to an end.
1994: Dual roles in The Odyssey
Between 1993 and 1994, Reynolds starred in The Odyssey.
1995: First The Outer Limits Appearance
In 1995, Ryan Reynolds made his first appearance in The Outer Limits in the episode "If These Walls Could Talk".
1996: Cameo Appearances and Co-starring role
In 1996, Ryan Reynolds made cameo appearances in The X-Files and The John Larroquette Show and co-starred in the television film Sabrina the Teenage Witch.
1997: Role in The Alarmist and The Outer Limits
In 1997, Ryan Reynolds returned to feature films with The Alarmist, and appeared in The Outer Limits.
1998: The Outer Limits appearance
In 1998, Ryan Reynolds appeared in The Outer Limits.
1998: Breakthrough Role in Two Guys and a Girl
In 1998, Ryan Reynolds had his breakthrough role as medical student Michael "Berg" Bergen in Two Guys and a Girl.
1999: Roles in Coming Soon and Dick
In 1999, Ryan Reynolds took on minor roles in the comedies Coming Soon and Dick.
2000: Starring in Boltneck
In 2000, Ryan Reynolds starred as Karl in the horror comedy Boltneck.
2000: Development of Deadpool film
The superhero film "Deadpool" which Ryan Reynolds starred in, began development as early as 2000.
2001: Role in Finder's Fee
In 2001, Ryan Reynolds portrayed Quigley in the drama thriller Finder's Fee.
2001: Two Guys and a Girl ends
In 2001, Ryan Reynolds' role in Two Guys and a Girl came to an end.
2002: Starring in National Lampoon's Van Wilder
In 2002, Ryan Reynolds played the titular character in the romantic comedy National Lampoon's Van Wilder, which achieved box office success.
2003: Roles in The In-Laws and Foolproof
In 2003, Ryan Reynolds portrayed Mark Tobias in The In-Laws and starred in Foolproof.
2004: Cameo Appearance, Voice Acting Debut, and Starring in Blade: Trinity
In 2004, Ryan Reynolds had a cameo appearance in Harold & Kumar Go to White Castle, made his voice acting debut in Zeroman, and starred in Blade: Trinity.
2004: Harold & Kumar Go to White Castle
In 2004, Ryan Reynolds starred in Harold & Kumar Go to White Castle, one of his most acclaimed films according to Rotten Tomatoes.
2004: Starring in Blade: Trinity
In 2004, Ryan Reynolds starred in the critically unsuccessful superhero film Blade: Trinity.
2005: Interest in Deadpool Film Adaptation
As early as 2005, Ryan Reynolds expressed interest in and involvement with a potential Deadpool film adaptation.
2005: Roles in The Amityville Horror, Waiting..., and Just Friends
In 2005, Ryan Reynolds starred in The Amityville Horror, Waiting..., and Just Friends.
2005: Starring in Waiting...
In 2005, Ryan Reynolds starred in the commercially successful romantic comedy Waiting....
2006: Starring in Smokin' Aces
In 2006, Ryan Reynolds played FBI agent Richard Messner in the crime action film Smokin' Aces.
2007: Starring in The Nines
In 2007, Ryan Reynolds played three distinct characters in The Nines, exploring themes of reality, identity, and the nature of existence.
2008: Running New York City Marathon for Team Fox
In 2008, Reynolds ran the New York City Marathon for Team Fox to support the Michael J. Fox Foundation.
2008: Roles in Chaos Theory, Definitely, Maybe, and Fireflies in the Garden
In 2008, Ryan Reynolds played Frank Allen in Chaos Theory, Will Hayes in Definitely, Maybe, and a successful novelist in Fireflies in the Garden.
2009: Joining the Board of the Michael J. Fox Foundation
In 2009, Reynolds joined the board of the Michael J. Fox Foundation to support research for a cure for Parkinson's disease.
2009: Portrayal of Wade Wilson / Weapon XI in X-Men Origins: Wolverine
In 2009, Reynolds portrayed Wade Wilson / Weapon XI in "X-Men Origins: Wolverine", which led to his deeper involvement in the development of "Deadpool".
2009: Roles in Adventureland, X-Men Origins: Wolverine, The Proposal, and Paper Man
In 2009, Ryan Reynolds starred in Adventureland as Mike Connell, played Wade Wilson / Deadpool / Weapon XI in X-Men Origins: Wolverine, starred as Andrew Paxton in The Proposal, and played Captain Excellent in Paper Man.
2009: Adventureland Film
In 2009, Ryan Reynolds starred in Adventureland, one of his most acclaimed films according to Rotten Tomatoes.
2009: Starring in The Proposal
In 2009, Ryan Reynolds starred in the commercially successful romantic comedy The Proposal.
2010: Guest Appearance on Sesame Street and Starring in Buried
In 2010, Ryan Reynolds made a guest appearance on Sesame Street and starred in the Spanish and American survival thriller film Buried.
2010: Buried Film
In 2010, Ryan Reynolds starred in Buried, one of his most acclaimed films according to Rotten Tomatoes.
2011: Starring in Green Lantern, The Change-Up, and Executive Producing The Whale
In 2011, Ryan Reynolds starred in Green Lantern and The Change-Up, and executive-produced and narrated the documentary film The Whale.
2011: The Whale Film
In 2011, Ryan Reynolds starred in The Whale, one of his most acclaimed films according to Rotten Tomatoes.
2011: Starring in Green Lantern
In 2011, Ryan Reynolds starred in the critically unsuccessful superhero film Green Lantern.
2012: Starring in Safe House and cameo in Ted
In 2012, Ryan Reynolds starred in the action thriller "Safe House" alongside Denzel Washington, playing a CIA agent named Matt Weston. He also made a cameo appearance as Jared in the comedy "Ted" in 2012.
2013: Role in R.I.P.D.
In 2013, Reynolds played Nick Walker in "R.I.P.D.", a detective murdered by his partner.
2013: Voice acting in The Croods and Turbo
In 2013, Ryan Reynolds lent his voice to animated films, including The Croods and Turbo.
2013: Voice roles in The Croods and Turbo and leading role in R.I.P.D.
In 2013, Ryan Reynolds voiced Guy in "The Croods" and the titular character in "Turbo". He also played Nick Walker in "R.I.P.D." in 2013.
2014: 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," acknowledging his extensive and varied career roles.
2014: Roles in The Voices and The Captive
In 2014, Ryan Reynolds starred as Jerry Hickfang in "The Voices", and portrayed Matthew in the psychological thriller "The Captive".
2015: Starring 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 appeared in the science fiction film "Self/less".
2015: Mississippi Grind Film
In 2015, Ryan Reynolds starred in Mississippi Grind, one of his most acclaimed films according to Rotten Tomatoes.
2015: Starring in Woman in Gold
In 2015, Ryan Reynolds starred in the biographical drama Woman in Gold.
2016: Starring in Deadpool
In 2016, Ryan Reynolds achieved commercial success as the titular character in Deadpool and received a Golden Globe nomination for his performance.
2016: Critical and Commercial Success with Deadpool
In 2016, Ryan Reynolds achieved significant success with "Deadpool", grossing $782 million. He played Wade Wilson / Weapon XI, reprising a role he had previously played in X-Men Origins: Wolverine.
2016: Supporting role in Criminal
In 2016, Ryan Reynolds had a supporting role as Bill Pope in the action thriller "Criminal".
2016: Deadpool Film
In 2016, Ryan Reynolds starred in Deadpool, one of his most acclaimed films according to Rotten Tomatoes.
2017: Appearing in Life
In 2017, Ryan Reynolds appeared in the sci-fi horror Life.
2017: Release of The Hitman's Bodyguard
In 2017, Ryan Reynolds starred in The Hitman's Bodyguard, playing Michael Bryce.
January 2018: Launch of Maximum Effort and First-Look Deal with Fox
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, written by Deadpool screenwriters.
February 2018: Acquisition of 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: Release of Deadpool 2
In 2018, "Deadpool 2" was released and became a commercial success, grossing $715 million.
2018: Deadpool 2 Film
In 2018, Ryan Reynolds starred in Deadpool 2, one of his most acclaimed films according to Rotten Tomatoes.
November 2019: Ownership stake in Mint Mobile
In November 2019, Ryan Reynolds purchased an ownership stake in Mint Mobile, holding between 20% and 25%.
2019: Appearing in 6 Underground and Detective Pikachu
In 2019, Ryan Reynolds appeared in action films like 6 Underground and lent his voice to the animated character Pikachu in Detective Pikachu.
2019: Voicing Detective Pikachu and starring 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: Reading of James and the Giant Peach
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: Assistance in recovering stolen teddy bear
In July 2020, Ryan Reynolds and broadcaster George Stroumboulopoulos each offered $5,000 for the return of a stolen teddy bear belonging to a Vancouver woman. The teddy bear was recovered within a few days.
September 2020: Talks to purchase Wrexham
In September 2020, talks began for Ryan Reynolds and Rob McElhenney to purchase the Welsh soccer club Wrexham.
November 2020: Takeover of Wrexham confirmed
In November 2020, the takeover of the Welsh soccer club Wrexham by Ryan Reynolds and Rob McElhenney was confirmed.
2020: Reynolds reflects on The Voices
In 2020, 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: Reprising 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: The Croods: A New Age Film
In 2020, Ryan Reynolds starred in The Croods: A New Age, one of his most acclaimed films according to Rotten Tomatoes.
2020: Animated Films
In 2020, Ryan Reynolds was acting in The Croods franchise.
2020: Second-Highest-Paid Actor
In 2020, Ryan Reynolds was the world's second-highest-paid actor.
February 2021: Approval from Financial Conduct Authority for Wrexham takeover
In February 2021, the takeover of Wrexham by Ryan Reynolds and Rob McElhenney 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. Ryan Reynolds has used Maximum Effort to create advertisements for his film projects and brands.
October 2021: Announcement of Sabbatical
In October 2021, Ryan Reynolds announced he would be taking "a little sabbatical" from his work after the production of Spirited.
2021: Starring in Free Guy and Red Notice
In 2021, Reynolds starred in "Free Guy", portraying a non-playable character who realizes he is living in a video game, and in "Red Notice" as a renowned art thief.
2021: Appearing in Free Guy
In 2021, Ryan Reynolds appeared in action films like Free Guy.
2021: Free Guy Film
In 2021, Ryan Reynolds starred in Free Guy, one of his most acclaimed films according to Rotten Tomatoes.
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.
2022: Pledge 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: Appearing in The Adam Project
In 2022, Ryan Reynolds appeared in action films like The Adam Project.
2022: Pursuit of Ottawa Senators Ownership
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: Starring in The Adam Project and Sabbatical Announcement
In 2022, Ryan Reynolds starred in "The Adam Project" and announced he was taking "a little sabbatical" after the production of "Spirited".
2022: Welcome to Wrexham release
In 2022, the Emmy Award-winning television series Welcome to Wrexham, documenting Ryan Reynolds' co-ownership of Welsh soccer club Wrexham, was released.
March 2023: T-Mobile's acquisition of Mint Mobile
In March 2023, T-Mobile announced its acquisition of Mint Mobile in a deal worth up to $1.35 billion, a company Ryan Reynolds invested in.
April 2023: Investment in Nuvei
In April 2023, Canadian payments technology company Nuvei announced that Ryan Reynolds had invested in the company.
August 2023: Donation 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.
October 2023: Donation 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 between Israel and Gaza.
August 2024: Box Office Success for Reynolds and Lively
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. "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 hurricanes Helene and Milton.
2024: Deadpool & Wolverine Film
In 2024, Ryan Reynolds starred in Deadpool & Wolverine, one of his most acclaimed films according to Rotten Tomatoes.
2024: Starring in Deadpool & Wolverine
In 2024, Ryan Reynolds starred in Deadpool & Wolverine, which emerged as his highest-grossing release.
September 2025: Box Office Gross
As of September 2025, Ryan Reynolds' films have grossed over $6.6 billion worldwide.
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