From the fluid cinematography of Doug Emmett to Mary Elizabeth Winstead’s obvious transition into an undeniable star, the directorial debut of Chris Messina, Alex of Venice, contains a natural honesty that simply feels right.

As an actor, Messina has assembled an impressive resume over the last 15 years, beginning with his debut in John Dahl’s Rounders. More recently, he’s starred in Damages, The Newsroom and The Mindy Project, so given his incredible range as a performer, it was a pleasant surprise to learn of Messina’s debut behind the camera. And what a way to kick off a directing career with the severely underrated Winstead as his star. Both Massina and his actress channel the contained intensity of John Cassavetes’ LA-based A Woman Under the Influence, as the Venice Beach location provides a beautiful backdrop for a study of the human element.

At the heart of Alex of Venice is Chekhov’s final play, The Cherry Orchard. Inspired by memories of an industrial takeover of his beloved garden and a swindling of his Mother (forcing her into debt), the writer penned the story of materialism and further established his legacy. In Messina’s film, a young mother named Alex (Winstead) struggles to cope with a distant husband (Messina) and the onset of her father’s Alzheimer’s disease. Furthermore, she’s an eco-conscious lawyer trying to prevent the construction of a new spa. For Alex, her passion extends beyond the immediate future — it’s about legacy. She’s constantly wound up and attempts to juggle a full load of responsibilities, which prompts her live-in father (Don Johnson) to summon Alex’s eclectic sister Lily (Katie Nehra) for help. Watching from the sidelines is young Dakota (Skylar Gaertner), who removes himself from the domestic three-ring circus.

When Alex’s husband drifts away and her maternal stress intensifies, it’s the foul-mouth Lily that offers comedic relief and a new perspective. It’s not that Alex lives a conservative life, she’s just used to being a Mom and considers herself a “weirdo” for having only one sex partner. Through a rather convenient twist, she hooks up with an ambitious businessman (Derek Luke) — the same man Alex is fighting against — but only after an overt attempt at seduction fails miserably with a distracted co-worker.

The gentle score enhances the visual imagery of Messina’s film, and Winstead’s natural glow reminds of her famous relative Ava Gardner. She’s always been a joy to watch on screen, however the increasing command of her skills makes Winstead the ultimate indie actress. If the sound dropped, she could still keep viewers in their seats just like Renée Jeanne Falconetti in Dreyer’s The Passion of Joan of Arc. And so, one has to wonder if there’s any significance to Messina’s title.

As a director, Messina offers an insightful take on familial bonds and timely societal issues. At a crucial moment, Alex willingly drops ecstasy with her sister, yet the scene doesn’t take on a didactic tone. Instead, Alex enjoys a brief moment of happiness; a departure from reality. The camera remains at a safe distance throughout the film and peers through open spaces as the drama unfolds. As a result, a poignant close-up shot of Alex’s brief escape becomes even more powerful.

The cast — wow. Of course, there’s Winstead, but Katie Nehra will have you immediately googling Alex of Venice for her name. With a striking presence, she provides numerous laugh-out-loud moments and compliments Winstead exceptionally well. Meanwhile, Don Johnson manages to deliver a genuinely touching performance that could easily have gone the other way. He’s believable throughout and lends weight to the acting of his fellow performers. And one can’t forget about the always-entertaining Derek Luke.

It’s exciting to imagine what subject matter Chris Messina will tackle in the future, but until then, Alex of Venice stands alone as a relevant and well-executed piece of work.

Q.V. Hough (@qvhough) is a freelance writer and founder of Vague Visages. He lived in Hollywood, California from 2006 to 2012 and graduated from Minnesota’s Concordia College in 2004 with bachelor degrees in Communication-Mass Media and History. He now resides in Fargo, North Dakota.