Movie Review: 'She's in Portland' Sideways for a new Generation

She's in Portland stars Tommy Dewey as Wes, a rich successful, still relatively young man, in a rut. Wes has problems that he's not fully prepared to confront but they are about to come to a head. Wes is being sent out west to his company's west coast branch to complete a deal. While he's on the coast he intends on seeing his friend Luke (Francois Arnaud), his best friend who has been ghosting him for over a month.

The trip gains a newfound importance after Luke blows off Wes's invitation to their High School reunion. At the reunion, alongside his wife, Sarah (Mnka Kelly), Wes sees Maggie (Nicole LaLiberte), the one time love of Luke's life. When Maggie asks about Luke and un-casually drops in that she's single, Wes gets the idea that he will take Luke to find her.

Why does this mean so much to Wes? It's not very clear, but that's not really the point. Wes is desperate for a reason to reconnect with the lost soul of his best friend and the road trip is an excuse to do just that. Wes also has a deep dark secret that he's carrying with him on the trip that threatens to derail not just the trip, but the modest construct of his suburban Dad existence.

She's in Portland was co-written and directed by Marc Carlini and quite nakedly lifts from the angsty road trip tropes of Alexander Payne's seminal mid-life crisis romance, Sideways. From the male bonding premise to the California setting, to the secrets and lies about fidelity, loss, marriage and friendship, She's in Portland doesn't so much rip off Sideways as bear the weight of its influence.

Tommy Dewey is an actor whose face seems very familiar but I could not place it. He looks like one of those guys who plays the bully at work to someone like an Adam DeVine or in another era, Ed Helms or Jason Bateman. He has that permanent smugness to him and yet, he's perfectly cast here. Dewey overcame my reservations and typecasting and proves a compelling and charismatic presence.

I also enjoyed the subdued sadness of Francois Arnaud whose Luke is at a fearful crossroads. Having crossed my own threshold of fear about the future and financial security versus living for a dream, I was feeling Luke's story on a deeper level. It's scary to reach a particular age in life and no that you have no safety net and it's tempting to give in to a comfortable form of defeat.

Yes, the themes of She's in Portland are laid on rather thick with Maggie, more metaphor than character. Maggie, quite obviously, represents following your dreams versus giving into despair and so on but I didn't mind the heavy-handedness of She's in Portland. These two actors and a series of brilliant cameos from beautiful, brilliant supporting actresses help make She's in Portland tolerably thick with metaphor, meaning and humor.

I was especially taken with Lola Glaudini and Joelle Carter as a pair of women who find themselves within their own parallel movie to Dewey and Arnaud. In another universe, they are starring in a He's in Portland or some such journey and it's just as entertaining, lively and intriguing. Glaudini is wonderful as an independent and spirited woman free from the binds of convention.

The pairs of women that Wes and Luke meet along their journey are quite obviously representative of a tour of their past lives, past loves and paths not taken. A pair of college students remind them of their youth, Glaudini and Carter of the life still to be lived and two more women who represent the poor choices they need to avoid also pop in for a moment.

She's in Portland is a lovely movie with a gorgeous California setting. It's the kind of setting that makes you want to buy an open top jeep and drive up the PCH for days seeking youth and adventure. The setting would be hard not to make look gorgeous but much credit to Cinematographer Devin Whetstone who captures the beauty at its most appealing.

She's in Portland is modest, entertaining and occasionally moving. The leads have a genuine, flawed appeal and the women are all just incredible. The script, co-credited to Patrick Alexander, has charm for days. All of that combined with the gorgeous setting makes She's in Portland impossible not to recommend.

Fans of Sideways may especially enjoy She's in Portland as a reminder of how movies can portray wonderfully flawed men with genuine empathy while not letting them off the hook when they suck. Like Sideways, there is soul and romance at the heart of She's in Portland and that is unquestionably the films biggest asset.