Courting Courtney is a 1997 independent comedy film which include the likes of various older and future improv/stand-up comedians. The cast includes: Ann Gasteyer (Saturday Night Live, The Good Wife), Sean Masterson (Improv-A-Ganza, Drew Carey's Green Screen Show), Kathy Griffin, character actor Taylor Negron, Chris Hardwick (future host of the The Nerdist and @midnight), stand-up comedian Dana Gould (The Simpsons), Ian Gomez (The Drew Carey Show), Ryan Stiles and Julia Sweeney (Saturday Night Live, Pulp Fiction).
Filmmaker Nick has decided to make a documentary about his best friend Courtney's love life. Courtney, a schoolteacher, has had a two-year on and off relationship with a guy who can't commit; she's also tried video-dating and a women's group. She never thought she'd have a problem finding the right guy and falling in love, but as she gets closer and closer to 30 she gets more and more desperate. Nick, on the other hand, is having as much trouble finding the right girl, and when his true feelings for Courtney come to light, they have to decide whether or not to stay just friends.