Film
Grillo started his acting career by appearing in commercials, for companies such as American Express and Sure deodorant. His first film role was in 1992's The Mambo Kings, and he went on to appear in the films Minority Report (2002), April's Shower (2006), and both iMurders and New Line Cinema's Pride and Glory in 2008.
Grillo was in the 2010 horror film Mother's Day in the role of Daniel Sohapi and the following year, had a supporting role in the 2011 film Warrior as MMA trainer Frank Campana. In 2012, he played Diaz in the survival thriller The Grey with Liam Neeson and as Sarge in End of Watch with Jake Gyllenhaal. In 2013, he starred with Jaimie Alexander in the romantic thriller film Collision and had a bit role in the action film Homefront with Jason Statham.
In 2014, Grillo was cast as Hydra agent Brock Rumlow in the 2014 film Captain America: The Winter Soldier. The same year, he starred as Sergeant Leo Barnes in the sequel The Purge: Anarchy, and reprised his role in 2016's The Purge: Election Year. He also reprised the role of Brock Rumlow/Crossbones in the third installment of the Captain America film series, Civil War, which was released on May 6, 2016.
In October 2013, Grillo started filming for The Crash, starring alongside Academy Award nominee Minnie Driver, Ed Westwick, AnnaSophia Robb, Dianna Agron, John Leguizamo, Mary McCormack, Christopher McDonald and Maggie Q. The film is directed by Aram Rappaport and produced by Hilary Shor, Atit Shah, and Aaron Becker. The Crash was released on January 31, 2017.
In 2015, Grillo starred in the films Demonic and Big Sky. Another film in which he stars, Beyond Skyline, was originally set for release in 2015, and was ultimately released on Netflix in December 2017.
In 2018, Grillo starred opposite Bruce Willis and Johnathon Schaech in the action film Reprisal. Years after its release, the film made it on Netflix's U.S. top five in October 2021.
In 2019, Variety announced that Grillo has signed with Creative Artists Agency (CAA) for representation.
Grillo produced and starred in Boss Level, which was announced in November 2017 and was originally scheduled to be released by Entertainment Studios Motion Pictures on August 16, 2019, but was delayed. It was subsequently bought by Hulu, which released it on March 5, 2021. He also appeared in the sequel Hitman's Wife's Bodyguard with Ryan Reynolds and Samuel L. Jackson.
More recently, he has appeared in the films This Is the Night with Naomi Watts, Copshop with Gerard Butler, Ida Red with Melissa Leo, The Yacht with Ruby Rose and A Day to Die with Bruce Willis.
Grillo plays Ferruccio Lamborghini in the 2022 biographical drama Lamborghini: The Man Behind the Legend. The film is directed by Oscar-winning writer Bobby Moresco. The film also stars Oscar winner Mira Sorvino and Emmy nominee Gabriel Byrne.
In June 2024, set photos revealed that Grillo was set to appear in the DC Universe (DCU) film Superman as Rick Flag Sr., reprising the role in live-action after debuting as the character in the animated series Creature Commandos (2024–present).
