Powell plays mild-mannered college professor Gary Johnson — and his devil-may-care hit man alter ego, Ron.

For Powell, writing a screenplay with his longtime collaborator was a lifelong dream. “When I was 14, I worked with Rick for the first time,” Powell said. “And at that point, I thought, ‘Oh, my gosh, he’s one of the greats. I’m getting to be on a film set, a Richard Linklater film set.’ And now it’s 20 years later, and I look at Rick the same way. I just pinch myself every day that I get to be here.”

“[Glen] is a great collaborator,” Linklater said about his leading man and co-writer. The two first worked together when Powell was a teen actor in Linklater’s Fast Food Nation; they reunited on Everybody Wants Some!! and Apollo 10 ½ before writing Hit Man together. “It’s kind of like the sports team: If the best guy on the team is also the hardest working, you might win … That’s what Glen is. He wants everybody on the team to be great.”

Top Gun: Maverick, Hidden Figures, Everybody Wants Some!!, The Expendables 3, Devotion, Twisters, Scream Queens

Arjona (Andor, Triple Frontier) plays Madison, who tries to hire Ron and then becomes romantically entangled with him.

Arjona is the key to the romance at the core of the film. “Casting Madison was the crucial moment,” Linklater said. “It had to be someone a guy would risk everything they’ve worked for to be with. And yet, she had to be very sympathetic. Ultimately, what we were asking her to do is just be a real person.”

“Madison’s intentions in this movie are not exactly clear, and that’s one of the reasons why I love her so much,” Arjona said about diving into the role. “There’s an energy about Madison that is kind of contagious, erratic, and spontaneous. I’ve never played a character like that.”

Andor, Emerald City, Good Omens, Pacific Rim Uprising, Life of the Party, Morbius, Father of the Bride, Blink Twice

Jasper is the dirty cop whose suspension leads to Gary taking the fake hit man job; upon returning to the force, Jasper quickly becomes suspicious of his replacement.

“Even though Jasper is sort of the bad guy, you’ve always got to find something, a point of view, that will back up the character and justify why he’s doing what he’s doing. You could feel his anger and he was erratic, and the unpredictability of him had me turned on,” Amelio said. 

Indeed, Amelio was the only actor considered for the role. “As Rick and I were writing, there was no one we ever talked about or considered for the role of Jasper other than Austin Amelio,” Powell said. “We wrote this character for him. We had both worked with him on Everybody Wants Some!!, and he’s just one of those special actors who are fun to watch thinking and scheming. This character is very tough to play, but he makes it look so effortless.”

Everybody Wants Some!!, The Walking Dead, Fear the Walking Dead, Song to Song, Holler

Claudette is one of Gary’s police chaperones, the supervisor who’s in his ear on difficult assignments.

“Claudette was really me because it was written as a guy, Claude, and there wasn’t a whole lot to go on,” Retta said. “How do you research detectives? I’ve never even heard of a group of detectives who do sting operations for people trying to do hits on people, so I wouldn’t even know where to begin.”

Retta had history with both Linklater and Powell. She worked with the director on her first pilot, $5.15/Hr., and with Powell on the 2014 comedy Sex Ed. “An interesting fact about Retta is she’s also incredibly well versed in crime stories,” Powell said. “When Rick and I were constructing the through lines for how someone would die or what police would be looking for, Retta was our BS detector. She’d be like, ‘That would never happen. You would discover the body here.’ ” 

Parks and Recreation, Good Girls

Phil is Claudette’s partner, the tech guy in the van who happily swaps pants with Gary when he needs a more realistic hit man disguise. 

“Rick’s movies are extremely naturalistic. Coming from a comedy background, I was actually worried that I was going to be too big, making too big of gestures or too big a joke, or hitting things too on the nose for a Linklater film,” Rao said.

But Rao was pleasantly surprised at how things turned out on set. “At the end of our rehearsal period, I remember Rick told me, ‘Bring yourself to it.’ So, for me, it was not so much creating a character, but being myself,” he adds. “But I am still Phil, who moved to New Orleans, got into IT, and then ended up in this odd job with the police force.”

The One You’re With, Bad Romance, The Flight Attendant, Truth Be Told

Bernard plays Gary’s ex-wife Alicia, with whom he still shares a friendly relationship. 

Younger, Milkwater, Sully, The Intern, Chicago Med, Transparent, High Maintenance

Actor and stuntman Holtzman plays Madison’s husband, Ray, an abusive partner who incites her to visit a hit man in the first place.

Hidden Figures, The Inspectors, Westworld, Civil War

Actor and radio personality Banks plays the police sergeant whom Gary and co. report to. 

Queen & Slim, Green Book, The Banker, The Burial, NCIS: New Orleans, Queen Sugar, Treme