Reynolds's career began in 1991 when he starred as Billy Simpson in the Canadian-produced teen soap opera Hillside, distributed in the United States by Nickelodeon as Fifteen. In 1993, Reynolds played a child who moves from India to Canada after the death of his father in the film Ordinary Magic. Between 1993 and 1994, he had a recurring role in The Odyssey as Macro. In 1996, he had a supporting role as Jay "Boom" DeBoom in "Syzygy", the thirteenth episode of the third season of The X-Files, and co-starred with Melissa Joan Hart in the TV movie Sabrina the Teenage Witch. In 1996, Reynolds played Bobby Rupp, boyfriend of murdered teen Nancy Clutter, in a two-part miniseries, In Cold Blood, an adaptation of Truman Capote's non-fiction novel of the same name. He also appeared in the anthology The Outer Limits episode "Origin of the Species", which originally aired on November 14, 1998. Beginning in 1998, Reynolds starred in Two Guys, A Girl and a Pizza Place (later renamed Two Guys and a Girl), playing medical student Michael "Berg" Bergen throughout the show's four-season run. He starred in the National Lampoon movie Van Wilder in 2002, appeared in The In-Laws with Michael Douglas and Albert Brooks, and also in the Canadian production Foolproof in 2003.
Although he had performed primarily in comedies, Reynolds underwent intense physical training to play an action role as the character of Hannibal King in the 2004 film Blade: Trinity. The same year, he made a cameo appearance in Harold & Kumar Go to White Castle as a nurse. Reynolds played George Lutz in the 2005 remake of the 1979 horror film The Amityville Horror. Also in 2005, he played a waiter named Monty in Waiting... and appeared as music executive Chris Brander in the romantic comedy Just Friends alongside Amy Smart and Anna Faris. In Just Friends, Reynolds lip-synced "I Swear" over the end credits. Additionally, he played an FBI agent alongside Ray Liotta in the 2006 crime action film Smokin' Aces. Reynolds played the protagonist in the 2008 film Definitely, Maybe. He also appeared in the second-season finale of the television series Scrubs. In 2007, Reynolds guest-starred as Brendan's friend Hams in the episode "Douchebag in the City" of the TBS sitcom My Boys.

Reynolds portrayed Wade Wilson / Weapon XI in a supporting role in the prequel 20th Century Fox X-Men film, X-Men Origins: Wolverine, which was released in 2009. He had previously spoken of his interest and involvement in a possible film adaptation of Deadpool with screenwriter David S. Goyer as far back as 2005. 2009 also saw Reynolds portray Andrew Paxton, opposite Sandra Bullock, in The Proposal, and Mike Connell in Adventureland.

In 2010, Reynolds starred in the Spanish and American thriller

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In January 2018, Reynolds started the production company Maximum Effort and signed a three-year first-look deal with Fox. Maximum Effort is in development on a live-action adaptation of the board game Clue, to be penned by Deadpool writers Rhett Reese and Paul Wernick. On June 23, 2021, the marketing division of Maximum Effort Production was spun off as a separate company, and acquired by MNTN Software. Reynolds is the driving force of Maximum Effort and has created ads for a number of his film projects and for brands such as Peloton and R.M. Williams.

Reynolds acquired a stake in Aviation American Gin in February 2018. He stated that his interest went beyond that of an owner, and that he planned to oversee the product's creative direction as well as taking an active role in the business.

In November 2019, Reynolds purchased an ownership stake in Mint Mobile. It was later revealed that Reynolds owns between 20% and 25% of Mint Mobile. Reynolds and Mint founder David Glickman both served on the board of directors for The Michael J. Fox Foundation, and Glickman was impressed with Reynolds' marketing for Deadpool. He joined the board of Match Group in July 2020. In August 2020, Diageo announced it was acquiring Aviation American Gin in a deal valued at up to $610 million.

On September 23, 2020, the Wrexham Supporters Trust announced that a business partnership consisting of Reynolds and fellow actor Rob McElhenney was in talks to purchase the Welsh football club Wrexham AFC. On November 16, it was confirmed that Reynolds and McElhenney took over the club after receiving the backing of the Wrexham Supporters Trust. In February 2021, the Financial Conduct Authority approved their takeover of Wrexham. The process of Reynolds and McElhenney's investment in Wrexham was covered by the 2022 TV documentary series Welcome to Wrexham.

As soon as Reynolds and McElhenney became involved with Wrexham AFC, they also took interest in Welsh culture, specifically their use of Welsh language, with them first advertising their club takeover with a Welsh translator. Reynolds asked that Welsh subtitles be included with his Netflix movie Red Notice, which was also advertised within Wrexham. In 2022, Reynolds and McElhenney were awarded the Diolch Y Ddraig award by Welsh language TV station S4C for their role promoting Welsh culture.

On May 3, 2021, Ryan Reynolds was part of an investor group led by Greylock Partners that made a $750 million investment into Wealthsimple. Reynolds's exact ownership amount was …

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In October 2008, 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. Reynolds appeared in People's Sexiest Man Alive lists in 2007 and 2009, and was awarded the top honour in 2010. On February 12, 2012, Reynolds appeared on the BBC's Top Gear as the Star in a Reasonably-Priced Car. He posted a time of 1:43.7. On the May 13, 2018, broadcast of the South Korean reality television show King of Mask Singer, Reynolds had a special performance in the opening act, singing "Tomorrow".

For his work, Reynolds has received widespread recognition and accolades. After having a role in the Canadian drama series Hillside, he was nominated for a Young Artist Award in 1993. For his role as Deadpool in the 2016 Marvel film of the same name, he received the Critics' Choice Movie Award for Best Actor in a Comedy and a Golden Globe nomination in the same category. For the soundtrack of the 2018 sequel, he received a Grammy nomination for Best Compilation Soundtrack for Visual Media. His other achievements include three MTV Movie & TV Awards, three People's Choice Awards and a Saturn Award. He received the Primetime Emmy Award for Outstanding Unstructured Reality Program for producing the series Welcome to Wrexham.

On November 26, 2021, Governor General Mary Simon awarded Reynolds a Governor General's Performing Arts Award to recognize his philanthropic work and significant contributions to the cultural life of Canada. Sandra Bullock, Morena Baccarin, Michael J. Fox, and Hugh Jackman made pre-recorded speeches in support of, and to congratulate Reynolds on the award.

The appointment of Reynolds by his home province to the Order of British Columbia was announced on August 7, 2023. The honour was to be presented to Reynolds and his fellow recipients during a ceremony held in November 2023 in Victoria.

In 2023, he received the Robin Williams Legend’s Legacy of Laughter Award.

Reynolds was appointed an Officer of the Order of Canada on October 16, 2024, in recognition of his film career and philanthropy.