Always Woodstock

Always Woodstock, directed by first-time feature writer-director Rita Merson, is a prime example of why romantic comedies get a bum rap. The film hits the trifecta of what not to do when crafting a story about relationships: it spotlights cookie-cutter characters, includes unsurprising plot points and features banal dialogue. As a “bonus,” Always Woodstock also has a musical element: mediocre pop-folk tunes sung passably by the lead character, a struggling singer-songwriter.
Catherine Brown’s (Allison Miller) life implodes within the film’s first 15 minutes. She’s been forced to put her own music on hold while managing a New York record label’s most difficult pop diva (Brittany Snow). On the same day she’s fired by her clownish bosses over a misunderstanding with the pop star, she comes home early to find her actor fiancé (Jason Ritter) in the shower with his dialect coach. Despite the setup, Snow has little more than a cameo role, and Ritter only pops in on occasion to provide campy moments as a self-absorbed actor.
The film explores the often-tread quarter-life crisis, but instead of drawing on elements from more successful films like Reality Bites, Frances Ha, Drinking Buddies or even this year’s musically inspired Begin Again, Merson relies on hackneyed themes in her script, and Miller overcompensates, trying too hard to become the quirky, city girl-turned-country hipster.
Catherine, orphaned at a young age, moves back to her family’s home in Woodstock to take time for herself and her music. During a night out, she meets handsome doctor Noah (James Wolk, Mad Men’s Bob Benson), who coincidentally owns a renowned music venue and recording studio that belonged to his late mother. Wolk isn’t given much to do except moon at Miller with puppy dog eyes. His character is a little too perfect: he’s rich, a gentleman and throws great dinner parties, proven by the copious amounts of kale salad and red wine served to his guests. Despite the fairytale elements, from flirty stares to long walks at night and stargazing on covered bridge rooftops, there’s no chemistry between the actors or their respective characters. We simply don’t buy that Catherine and Noah are falling madly in love.