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. He started his acting career in the teen soap opera *Hillside* and gained recognition in the sitcom *Two Guys and a Girl*. He transitioned into films, starring in comedies like *National Lampoon's Van Wilder*, *Waiting...*, and *The Proposal*. He also took on superhero roles in *Blade: Trinity* and *Green Lantern*. He has gained more fame and notoriety in recent years for his production and entrepreneurial endeavours.
1979: Original Amityville Horror Release
In 2005, Ryan Reynolds played George Lutz in the remake of the 1979 horror film The Amityville Horror.
1991: Hillside Debut
In 1991, Ryan Reynolds began his acting career starring in the Canadian teen soap opera Hillside.
1993: Ordinary Magic
In 1993, Ryan Reynolds played a child in the film Ordinary Magic.
1993: Hillside End
In 1993, Ryan Reynolds' role in Hillside came to an end.
1993: Young Artist Award Nomination
In 1993, after having a role in the Canadian drama series Hillside, Ryan Reynolds was nominated for a Young Artist Award.
1994: The Odyssey
Between 1993 and 1994, Ryan Reynolds had a recurring role in The Odyssey as Macro.
1996: The X-Files & Sabrina the Teenage Witch
In 1996, Ryan Reynolds had a supporting role in The X-Files and co-starred in Sabrina the Teenage Witch.
November 14, 1998: The Outer Limits episode airs
On November 14, 1998, Ryan Reynolds appeared in The Outer Limits episode "Origin of the Species".
1998: Two Guys and a Girl
In 1998, Ryan Reynolds landed the lead role on the sitcom Two Guys and a Girl.
2000: Deadpool Film Development
As early as 2000, Deadpool was in development.
2001: Two Guys and a Girl End
In 2001, Ryan Reynolds' role in Two Guys and a Girl ended.
2002: National Lampoon's Van Wilder
In 2002, Ryan Reynolds starred in National Lampoon's Van Wilder.
2002: Van Wilder
In 2002, Ryan Reynolds starred in the National Lampoon movie Van Wilder.
2003: Foolproof
In 2003, Ryan Reynolds appeared in the Canadian production Foolproof.
2004: Blade: Trinity & Harold & Kumar Cameo
In 2004, Ryan Reynolds played Hannibal King in Blade: Trinity and made a cameo in Harold & Kumar Go to White Castle.
2005: Deadpool Film Adaptation
As far back as 2005, Ryan Reynolds had spoken of his interest and involvement in a possible film adaptation of Deadpool.
2005: The Amityville Horror & Waiting...
In 2005, Ryan Reynolds starred in The Amityville Horror and Waiting...
2006: Smokin' Aces
In 2006, Ryan Reynolds played an FBI agent in the crime action film Smokin' Aces.
2007: My Boys Guest Star
In 2007, Ryan Reynolds guest-starred in the episode "Douchebag in the City" of the TBS sitcom My Boys.
October 2008: Wrote for The Huffington Post regarding NYC Marathon
In October 2008, Ryan Reynolds wrote for The Huffington Post regarding his plan to run the 2008 New York City Marathon for his father who, at the time, suffered from Parkinson's disease.
2008: Definitely, Maybe
In 2008, Ryan Reynolds played the protagonist in the film Definitely, Maybe.
2009: X-Men Origins: Wolverine & The Proposal
In 2009, Ryan Reynolds portrayed Wade Wilson in X-Men Origins: Wolverine and starred in The Proposal.
June 17, 2011: Green Lantern Release
On June 17, 2011, Ryan Reynolds starred in Warner Bros.' film Green Lantern.
2013: The Croods Franchise Debut & Turbo
In 2013, Ryan Reynolds began voice acting in The Croods franchise and starred in Turbo.
2013: The Croods & R.I.P.D.
In 2013, Ryan Reynolds starred in The Croods and R.I.P.D.
2014: The Voices & The Captive
In 2014, Ryan Reynolds starred in The Voices and The Captive.
2015: Woman in Gold & Self/Less
In 2015, Ryan Reynolds starred in Woman in Gold and Self/Less.
2016: Deadpool Success
In 2016, Ryan Reynolds achieved commercial success with the film Deadpool.
2016: Critics' Choice Movie Award for Best Actor in a Comedy
In 2016, for his role as Deadpool in the Marvel film of the same name, Ryan Reynolds received the Critics' Choice Movie Award for Best Actor in a Comedy and a Golden Globe nomination in the same category.
June 2017: Deadpool 2 Filming
In June 2017, Ryan Reynolds began filming Deadpool 2.
2017: The Hitman's Bodyguard
In 2021, Reynolds reprised his role in Hitman's Wife's Bodyguard, a sequel to the 2017 film The Hitman's Bodyguard.
May 18, 2018: Deadpool 2 Release
On May 18, 2018, Deadpool 2 was released.
2018: Grammy Nomination for Best Compilation Soundtrack
For the soundtrack of the 2018 sequel, Ryan Reynolds received a Grammy nomination for Best Compilation Soundtrack for Visual Media.
January 2019: Armani Code Face
In January 2019, Ryan Reynolds was named the face of Armani Code.
January 2019: The Croods Sequel Return
In January 2019, it was announced that Ryan Reynolds would return as the voice of Guy in the sequel to The Croods.
April 2019: Free Guy Filming
Beginning in April 2019, Ryan Reynolds shot the science fiction action comedy film Free Guy.
May 2019: Detective Pikachu
In May 2019, Ryan Reynolds starred in Pokémon Detective Pikachu.
December 2019: Deadpool & Wolverine Announcement
In December 2019, Ryan Reynolds announced that Deadpool & Wolverine was in the works.
2019: 6 Underground & Detective Pikachu
In 2019, Ryan Reynolds starred in the action film 6 Underground and voiced Detective Pikachu.
May 2020: Read James and the Giant Peach for charity
In May 2020, Ryan Reynolds was among a group of celebrities who read an instalment of Roald Dahl's novel James and the Giant Peach in aid of Partners In Health.
June 11, 2020: Don't Premiere
On June 11, 2020, ABC's game show, Don't, premiered, with Ryan Reynolds as an executive producer.
September 23, 2020: Reynolds and McElhenney in talks to purchase Wrexham
On September 23, 2020, the Wrexham Supporters Trust announced that a business partnership consisting of Ryan Reynolds and Rob McElhenney was in talks to purchase the Welsh football club Wrexham.
2020: The Croods Franchise End
In 2020, Ryan Reynolds' voice acting in The Croods franchise ended.
February 2021: Takeover of Wrexham approved
In February 2021, the Financial Conduct Authority approved Ryan Reynolds' and Rob McElhenney's takeover of Wrexham.
May 3, 2021: Investment in Wealthsimple
On May 3, 2021, Ryan Reynolds was part of an investor group led by Greylock Partners that made a $750 million investment into Wealthsimple.
November 26, 2021: Governor General's Performing Arts Award
On November 26, 2021, Ryan Reynolds was awarded a Governor General's Performing Arts Award to recognize his philanthropic work and significant contributions to the cultural life of Canada.
2021: Starred in Three Films
In 2021, Ryan Reynolds starred in three films: Hitman's Wife's Bodyguard, Free Guy, and Red Notice.
January 2022: Investment in 1Password
In January 2022, Ryan Reynolds was part of a group of investors who participated in a Series C funding round that made a $620 million investment into 1Password.
March 2022: Donation to Water First
In March 2022, Ryan Reynolds and Blake Lively donated $500,000 to Water First, to provide indigenous people in Canada with clean water.
March 2022: The Adam Project Release
In March 2022, Ryan Reynolds starred in Netflix's science-fiction adventure film The Adam Project.
August 2022: Equity stake in FuboTV
In August 2022, Ryan Reynolds took an equity stake in FuboTV and announced a co-production partnership that will include the launch of the Maximum Effort Network on FuboTV.
November 2022: Interest in purchasing Ottawa Senators
In November 2022, Ryan Reynolds expressed interest in purchasing ownership of the Ottawa Senators, confirming his intentions on The Tonight Show and attending a Senators game.
2022: Awarded Diolch Y Ddraig award
In 2022, Ryan Reynolds and Rob McElhenney were awarded the Diolch Y Ddraig award by Welsh language TV station S4C for their role promoting Welsh culture.
2022: The Adam Project
In 2022, Ryan Reynolds starred in The Adam Project.
2022: Welcome to Wrexham documentary
In 2022, the process of Ryan Reynolds' and Rob McElhenney's investment in Wrexham was covered by the TV documentary series Welcome to Wrexham.
2022: Pledged donation for Ukrainian refugees
In the aftermath of the 2022 Russian invasion of Ukraine, Ryan Reynolds and Blake Lively pledged to "match up" to $1 million for Ukrainian refugees fleeing the conflict in Ukraine.
January 2023: Humanitarian Award at the Canadian Screen Awards
In January 2023, Ryan Reynolds was named the winner of the Academy of Canadian Cinema and Television's Humanitarian Award at the 11th Canadian Screen Awards.
March 15, 2023: T-Mobile acquires Mint Mobile
On March 15, 2023, T-Mobile announced it was acquiring Ka’ena Corporation, parent company of Mint Mobile, Ultra Mobile, and Plum, in a deal valued at up to $1.35 billion.
April 2023: Investment in Nuvei
During April 2023, Canadian payments technology company Nuvei announced that Ryan Reynolds had invested in the company.
May 2023: Withdrawal of bid for Ottawa Senators
Ryan Reynolds withdrew his bid to purchase the Ottawa Senators in May 2023.
May 23, 2023: Deadpool & Wolverine Filming
Filming of Deadpool & Wolverine began on May 23, 2023.
June 26, 2023: Investment in Alpine F1 Team
On June 26, 2023, it was announced that both Ryan Reynolds and Rob McElhenney were part of an investor group that bought a 24% equity stake in the Formula One Alpine F1 Team.
July 26, 2024: Deadpool & Wolverine Release
Deadpool & Wolverine opened on July 26, 2024.
August 2024: Box Office Domination
In August 2024, Ryan Reynolds and Blake Lively became the first married Hollywood couple to have separate films lead the box office on the same weekend with Deadpool and Wolverine.
October 2024: Relief fund contribution for Hurricanes Helene and Milton
Ryan Reynolds and Blake Lively voluntarily contributed a relief fund of $1 million in October 2024 to assist the States affected by Hurricanes Helene and Milton through Feeding American.
October 16, 2024: Appointed Officer of the Order of Canada
Ryan Reynolds was appointed an Officer of the Order of Canada on October 16, 2024, in recognition of his film career and philanthropy.
2024: Deadpool & Wolverine
In 2024, Ryan Reynolds starred in Deadpool & Wolverine.
