James Gandolfini 'didn't have a lot of confidence' acting in rom-com

James Gandolfini took on his first ever romantic comedy in the months before his tragic death on June 19 — and it didn’t come as naturally to the Sopranos star as his numerous tough-guy roles.

In Nicole Holofcener’s Enough Said, Gandolfini plays Albert, a divorcee who falls for Julia Louis-Dreyfus’ Eve, a divorced masseuse who’s facing an empty nest as her daughter prepares to leave for college. Eve loves Albert, but when she finds out that he’s the ex-husband of her friend/client, Marianne (Catherin Keener), she begins to question their relationship.

Louis-Dreyfus, who was cast first, loved the idea of working with Gandolfini. “When I brought up the idea of Jim, she was like, ‘Hell yeah! He’s sexy,’ says Holofcener. Unsurprisingly, the Veep actress felt more comfortable with the comedic stylings of Enough Said than Gandolfini. “Julia’s just a hilarious person,” says the director, who remembers a moment on set when she and Dreyfus simply could stop laughing. “We’re doubled over, and Jim is standing there like, ‘Oh my god, I think I signed up to be in a chick flick.’”

Gandolfini proved far more cerebral. “He would become pretty focused and serious,” says Holofcener. “[He] would ask a lot of questions of me, challenge me. He’s a complex person.” She continues, “Jim, I think, didn’t have a lot of confidence in himself comedically, which is a shame because he was very funny, and his timing was wonderful…. I wish that I could work with him again.”

Audiences will get to see Gandolfini in Enough Said when it hits theaters on Sept. 20 (and for a final time in 2014’s Animal Rescue). For now, you’ll have to settle for the just-released trailer: