Determined that his second feature would be more commercial, Anderson collaborated with Vaus on the screenplay for "Next Stop Wonderland" (1998), a quirky romantic comedy about a Boston-area nurse. The film earned positive notices and was favorably compared with Eastern European movies of the late 60s in its focus on the individual in scenes that uncover both the comedy of life and telling details of the character's day-to-day existence. After its initial showing at the 1998 Sundance Film Festival, "Next Stop Wonderland" was snapped up by Miramax for a reported $6 million.
Along with the release of "Wonderland", Anderson's deal with Miramax including working on an Americanized remake of the French film "When the Cat's Away", but that deal fizzled and he was replaced on the project. The hyphenate tackled yet another genre, this time sci-fi, when he crafted "Happy Accidents" (2000), a romantic comedy about a time-traveling man who returns to the past to woo and save a woman whose picture has intrigued him. Enhanced by strong turns by leads Marisa Tomei and Vincent D'Onofrio, the film debuted at the 2000 Sundance Film Festival where it was quickly snapped up by Paramount Classics. Along the road to actually opening in theaters, however, "Happy Accidents" fell out of favor with the studio. By the time IFC Films (which had funded the movie) decided to release it, Anderson had completed his fourth film "Session 9" (2001), a creepy thriller about a team hired to remove asbestos from an abandoned mental hospital. True to his credo about not repeating himself, the writer-director was mulling the idea of tackling an historical drama or a documentary as his fifth project.