Several of those films have testosterone-fueled buddy stories. "Varsity Blues" (1999), "Ready to Rumble" (2000), "Gone in 60 Seconds" (2000) and "Boiler Room," an indie film released last year about a group of hyper-aggressive young brokers, all feature gangs of guys, with Caan typically cast as a scrappy team player.
The actor also gravitates to a strong male point of view in his own writing.
"I have a lot of good male friends, and I think the things my friends say are hysterical; I think my strong point is writing dialogue between guys and girls. It's 'do what you know."'
For "Almost Love," Caan drew on his own mixed feelings about monogamy. "I've had the same girlfriend now for the past year and a half," he says. "We've broken up like eight times. I'd want to be with her when I wasn't with her, then when I \o7 was\f7 with her, I wanted to go out and have fun with other girls."
A few months ago, during one of the breakup phases, Caan began scribbling dialogue on scrap paper after a table-read for "Ocean's Eleven." "I just delved into that feeling of wanting her back."
Erik, the other male character in "Almost Love," goads Caan's lovelorn mope Danny into acknowledging the other side of the coin: He wants to be single.
Says Caan, "He's sort of like the other side of my brain. Not to discredit my girlfriend, but the play's really about my psyche, what goes on in my head. I think I know about the minds of young men.
"I dig the whole process so much, movies, plays, any theatrical activity. But with writing, all you need is a pad of paper."
If Caan has been working hard in recent years, he used to play even harder. "I was this scrappy little kid," he says. "I used to go out to clubs, and I used to like to drink and I used to like to rumble and get into trouble and stuff."
In 1998, Caan was involved in a nightclub brawl. "I woke up the next morning, and everything flashed in front of me. I said, you know, '[Forget] this. I want to be successful."'
Not that Caan regrets the partying years. "I'm glad I grew up in Los Angeles," he says. "A lot of kids come here from other towns, they want to be actors, and they get sucked into the whole Hollywood thing and having fun, then they're 27 before they settle down.
"I was doing all that stupid [stuff] when I was 15 years old, so by the time I was 19, I was already done with it. I decided to buckle down and really work hard.
"Now my drug is writing or acting, being creative. I can't sit still for 10 minutes."
Which is good. The green light keeps pulsing on his computer. For Scott Caan, work awaits.
"Almost Love," at Playhouse West, 10634 W. Magnolia Blvd., North Hollywood. Today through Saturday at 8 p.m., Sunday at 7 p.m., Sept. 9, 16 and 23 at 7 p.m. and Sept. 15 and 22 at 8 p.m. Donation. (310) 550-3536.