Jack Harlow Gives Matt Damon Criminal Advice in Trailer for Heist Movie ‘The Instigators’

Jack Harlow is set to star alongside Matt Damon and Casey Affleck in Apple TV+‘s The Instigators, and the crime comedy received its first trailer on Thursday (June 13).

Damon, who plays an ex-Marine named Rory, wants to pull off a heist, but is a novice in the robbery business. Luckily, Harlow and company are experts in the field, and are willing to help the much older Rory make it happen, but that comes with a price too.

“Just say, ‘I have a gun,'” Harlow hilariously advises Rory when the latter asks how to get people to listen to his orders. When the former Marine starts taking notes, the rapper-actor questions, “What are you doing?!”

Fittingly for Damon, the movie is staged in South Boston, with Fenway Park playing host in certain scenes, and former New England Patriots star Rob Gronkowski making a cameo in the film.

Directed by Doug Liman (The Bourne Identity, Road House, Mr & Mrs. Smith), The Instigators hits Apple TV+ on Aug. 9. In addition to Damon and Harlow, the cast includes Casey Affleck, Hong Chau, Alfred Molina, Michael Stuhlbarg, Paul Walter Hauser, Ron Perlman and more.

The new film is not Jack Harlow’s first foray into Hollywood. He made his acting debut in 2023’s White Men Can’t Jump reboot.

“It’s either just going to be there was an announcement you were in a movie and nothing else, or you get that, and it’s like, ‘Wow, and you brought it. You brought it,’” the “Lovin On Me” hitmaker told Zane Lowe after securing his first role. “So, I’m starting to look at it how I look at the music, and it’s my first one, so I care a lot about it.”

Watch a trailer for The Instigators below.