"Eternal Sunshine of the Spotless Mind"
"Eternal Sunshine of the Spotless Mind" set the gold standard for contemporary films that subvert romantic comedy conventions. Where many rom-coms render viewers numb with their transparent formula, Charlie Kaufman's narrative labyrinth, blending memories and dreams, was refreshingly stimulating in an era of feeble Heigl and Aniston vehicles. While none of the performances in the film falter, Jim Carrey arguably reached a career high with his portrayal of Joel, a devastated lover revisiting memories in the process of being erased. Michel Gondry's lush and colorful direction cement the film as a modern classic.

"Kissing Jessica Stein"
Before Jennifer Westfeldt directed her first feature "Friends With Kids," she co-penned this winning and insightful romantic comedy about a unlucky in love copy editor, Jessica (Westfeldt), who tries her hand at being bisexual after coming across a personal ad in the newspaper posted by a woman seeking a meaningful relationship (co-writer Heather Juergensen). To Jessica's surprise, she takes to the ad's author, Helen, a gallery owner who has her own share of hardships with the opposite sex. Things get messy (as they always do in rom-coms) when one of the pair wrestles with whether she's in it for the long haul, but the way Westleft and Juergensen deal with the denouement is anything from typical.

Woody Allen's "Manhattan" retains the romantic comedy framework while examining several dark and flawed romances. Building upon "Annie Hall's" sentimental story of a promising relationship's painful collapse, "Manhattan" begins with a middle aged writer, Isaac (Allen), being involved with a seventeen year old girl, a romance that both Isaac and the audience know is fundamentally amiss. Beyond the comedic facade are marriages fraught with infidelity and discontent. The black and white film stock and iconic Gershwin soundtrack imbue "Manhattan" with a sense of mythic weight and melancholy that heighten the film's dramatic moments. Though the film ends with a promise of redemption, the romantic relationships in "Manhattan" leave none unscathed.