[7] Grillo graduated from New York University with a business degree and spent a year on Wall Street before being asked to do a Miller Genuine Draft beer commercial.

[11] In 2012, he played Diaz in the survival thriller The Grey with Liam Neeson and as Sarge in End of Watch with Jake Gyllenhaal.

[17] 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.

[25] 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.

[27] 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.

[33][34] Grillo first appeared on television in episodes of Silk Stalkings (1993), and Poltergeist: The Legacy (1996) before being cast as oil tycoon Hart Jessup on the daytime soap opera Guiding Light in 1996 up until 1999.

[11] He was in the first and only season of The Kill Point in 2007, and played the role of Jimmy in the CSI: NY episode "The Things About Heroes," which aired in November 2007.

[38] Between 2014 and 2017, Grillo starred in the DirecTV drama series Kingdom as MMA coach Alvey Kulina alongside Nick Jonas and Jonathan Tucker.

[39] Grillo was a season 5 regular on the drama series Billions, starring as artist Nico Tanner opposite Damian Lewis and Maggie Siff.

[45][non-primary source needed] Grillo met actress Wendy Moniz in 1996 on the set of Guiding Light.