I'm Reed Fish (2006)

Synopsis
Reed Fish (Jay Baruchel of Million Dollar Baby and Undeclared) seems to be leading the life he's supposed to. He's followed in the footsteps of his late father, doing an early-morning radio show with the town's mayor, Maureen (Katey Sagal), through which the eccentric locals of Mud Meadows voice their complaints and have them addressed. He produces the show with his old high school buddy, Frank (Victor Rasuk), and he's engaged to be married to another high school chum, the gorgeous Kate Peterson (Alexis Bledel), whose dad (Blake Clark) seems to own every business in town. But Reed's plans are upended when his high school sweetheart, Jill (Schuyler Fisk), comes back to town. She's supposed to be away at law school, but she confides to Reed that she quit school years ago, and has been working as a waitress while she fruitlessly pursues a career in music. Reed encourages her to play on Open Mike Night at the local bar. He inspires her to find her voice, which leads to some complications in his relationship with Kate, forcing Reed to reexamine every aspect of his safe, secure life. I'm Reed Fish also features performances by DJ Qualls, Chris Parnell, and Shiri Appleby. The comedy marks the feature debut of director Zackary Adler, and had its world premiere at the 2006 Tribeca Film Festival. ~ Josh Ralske, All Movie Guide