[2] Webber has twice directed former mumblecore[3][4][5] actress Greta Gerwig, first in his film I Thought You Finally Completely Lost It and next in Northern Comfort, both shot primarily in a three-day shooting frenzy.

[12] In 2005, Webber began directing Monkfish starring Lloyd Kaufman,[13] and Tiny The Terrible, which debuted May 11, 2005 at The Paradise Rock Club in Boston.

Unsuccessful in helping Tiny's case through legal channels, Webber released a new feature-length documentary, American Psych Ward about Tunstall's unlawful imprisonment.

The film was delayed until May 28, 2010, by which time, Gerwig had gone on to her mainstream acting career with titles such as Greenberg starring Ben Stiller.

According to The Boston Globe, Webber and Gerwig create "ornery sparks",[18] and The Weekly Dig called him the "Anti-James Cameron" as a result.