This month Ryan Ross, a 32-year-old Dallas native, makes his directorial debut with Wheeler, about a Kaufman cowboy who goes to Nashville to pursue his songwriting dream. The micro-budget feature, a collaboration between Ross and star/co-writer Stephen Dorff, wouldn’t exist if the seventh-generation Texan hadn’t understood one cardinal rule of showbiz: Don’t be shy about fraternizing above your pay grade.

Ross broke into movies, after all, only because he befriended director Richard Linklater’s producer Anne Walker-McBay during a high school road trip to Austin. When he matriculated at UT-Austin, she hooked him up with an internship on Linklater’s Boyhood, followed by another internship on A Scanner Darkly. “It’s a kid’s ultimate dream to work on a movie,” Ross recalls, exhibiting the sort of over-the-top enthusiasm that occasionally irked his colleagues on the set. Like when he delivered lunch to a rehearsal and tried—unsuccessfully—to  stick around as Keanu Reeves worked on his lines. Or when he lingered too close to the video monitors where Linklater watched each take. “They had to give me a talking-to sometimes,” he admits. “A lot of the crew was maybe not a huge fan of me.”

But the way Ross tells it, it wasn’t always his fault. Take the Scanner production kickoff party, where he and Walker-McBay chatted with Winona Ryder and her brother Jubal. “Winona kept wanting to dance, because we had this live band,” Ross says. “But her brother was like, ‘I don’t want to dance. Dance with Ryan.’ So Winona grabs me, and we’re dancing. We had a blast, and she and I became friends.” Cue disapproval from various assistant-director types. “Someone kind of pulled me aside,” he recalls, “and said, respectfully, ‘Hey, you need to know your place.’ ” Laughing, Ross makes his defense: “Well, she asked me!

“Looking back, maybe I did step over some boundaries,” Ross admits. “But I think that’s what you have to do in this business. You kind of have to go for it, you know?”