In 2016, Reynolds found critical and commercial success with Deadpool, a film that had been in development as early as 2000.
After portraying Wade Wilson / Weapon XI, without the name Deadpool, in X-Men Origins: Wolverine, he became heavily involved in the development of a Deadpool film.
Deadpool featured a reboot of the character, ignoring the events of X-Men Origins: Wolverine, and establishing a new backstory for the character that was closer to the Marvel Comics source material.
The film takes place within the larger X-Men film universe, being made possible by the reset timeline in X-Men: Days of Future Past.
Deadpool made several box-office records, including: a worldwide opening of $264.9 million from 62 markets, which is the biggest of 2016, the biggest for an R-rated film, and the second biggest for Fox, only behind Star Wars: Episode III – Revenge of the Sith ($303.9 million).
It also recorded the biggest IMAX 2D worldwide opening of all time with $27.4 million from 606 IMAX theatres, eclipsing The Dark Knight Rises ($23.8 million).
The film's financial and critical success led the studio to move forward with a sequel.

Also in 2016, Reynolds had a supporting role in the Ariel Vromen-directed thriller Criminal.
On December 15, 2016, Reynolds received a star on the Hollywood Walk of Fame, at 6801 Hollywood Boulevard.
Reynolds co-starred with Jake Gyllenhaal and Rebecca Ferguson in the science fiction thriller Life in 2017, which reunited him with Safe House director Daniel Espinosa.

Reynolds began filming Deadpool 2 in June 2017.
The film opened on May 18, 2018.
In May 2019, he starred as the titular character in Pokémon Detective Pikachu, a live action film adaptation of the Detective Pikachu video game.
Reynolds voiced, and was the facial motion capture actor for the CGI detective Pikachu.

In January 2018, Reynolds signed a three-year first-look deal with Fox, starting development on a live-action adaptation of the board game Clue, to be penned by Deadpool writers Rhett Reese and Paul Wernick.
Additionally, in April 2019, Reynolds shot Free Guy, an action comedy directed by Shawn Levy in which Reynolds will star as "a background character who realizes he's living in a video game.
With the help of an avatar, he tries to prevent the makers of the game from shutting down his world".
In January 2019, it was announced that he would return as the voice of Guy in the sequel to The Croods.

In January 2019, Reynolds was named the face of Armani Code leading with a campaign for their Absolu scent.
On April 8, 2019, it was announced that Reynolds will be the host of ABC's game show, Don't.

In 2018, it was announced that Reynolds was cast in the Netflix action thriller film 6 Underground, directed by Michael Bay.
The film was released on December 13, 2019.

Reynolds will star alongside Dwayne Johnson and Gal Gadot in Netflix's upcoming thriller Red Notice, written and directed by Rawson Marshall Thurber.
Reynold's is an executive producer of ABC's game show, Don't, which premiered on June 11, 2020.
In 2016, Reynolds found critical and commercial success with Deadpool, a film that had been in development as early as 2000. After portraying Wade Wilson / Weapon XI, without the name Deadpool, in X-Men Origins: Wolverine, he became heavily involved in the development of a Deadpool film. Deadpool featured a reboot of the character, ignoring the events of X-Men Origins: Wolverine, and establishing a new backstory for the character that was closer to the Marvel Comics source material. The film takes place within the larger X-Men film universe, being made possible by the reset timeline in X-Men: Days of Future Past. Deadpool made several box-office records, including: a worldwide opening of $264.9 million from 62 markets, which is the biggest of 2016, the biggest for an R-rated film, and the second biggest for Fox, only behind Star Wars: Episode III – Revenge of the Sith ($303.9 million). It also recorded the biggest IMAX 2D worldwide opening of all time with $27.4 million from 606 IMAX theatres, eclipsing The Dark Knight Rises ($23.8 million). The film's financial and critical success led the studio to move forward with a sequel.
Also in 2016, Reynolds had a supporting role in the Ariel Vromen-directed thriller Criminal. On December 15, 2016, Reynolds received a star on the Hollywood Walk of Fame, at 6801 Hollywood Boulevard. Reynolds co-starred with Jake Gyllenhaal and Rebecca Ferguson in the science fiction thriller Life in 2017, which reunited him with Safe House director Daniel Espinosa.
Reynolds began filming Deadpool 2 in June 2017. The film opened on May 18, 2018. In May 2019, he starred as the titular character in Pokémon Detective Pikachu, a live action film adaptation of the Detective Pikachu video game. Reynolds voiced, and was the facial motion capture actor for the CGI detective Pikachu.
In January 2018, Reynolds signed a three-year first-look deal with Fox, starting development on a live-action adaptation of the board game Clue, to be penned by Deadpool writers Rhett Reese and Paul Wernick. Additionally, in April 2019, Reynolds shot Free Guy, an action comedy directed by Shawn Levy in which Reynolds will star as "a background character who realizes he's living in a video game. With the help of an avatar, he tries to prevent the makers of the game from shutting down his world". In January 2019, it was announced that he would return as the voice of Guy in the sequel to The Croods.
In January 2019, Reynolds was named the face of Armani Code leading with a campaign for their Absolu scent. On April 8, 2019, it was announced that Reynolds will be the host of ABC's game show, Don't.
In 2018, it was announced that Reynolds was cast in the Netflix action thriller film 6 Underground, directed by Michael Bay. The film was released on December 13, 2019.
Reynolds will star alongside Dwayne Johnson and Gal Gadot in Netflix's upcoming thriller Red Notice, written and directed by Rawson Marshall Thurber. Reynold's is an executive producer of ABC's game show, Don't, which premiered on June 11, 2020.
Ryan Reynolds